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What’s better than a summer vacation on Cape Cod? A summer vacation that’s perfectly planned so you can spend more time relaxing and less time stressing. With its charming coastal towns, beautiful beaches, and endless activities, Cape Cod is the ultimate summer destination for families, couples, and groups of friends looking to soak up the sun and enjoy classic New England charm. The key to a stress-free getaway is planning early, ensuring you get the best accommodations, dining experiences, and activities lined up before the summer crowds arrive.

Explore the Best of Cape Cod’s Outdoor Activities

Summer on Cape Cod is all about enjoying the great outdoors. The region is home to some of the most stunning beaches in New England, each offering a unique experience. Whether you prefer the gentle waves of Mayflower Beach, the scenic beauty of Nauset Beach, or the iconic dunes of Race Point Beach, there’s a perfect stretch of sand for everyone. Early planning means you can secure parking permits, reserve beach chairs and umbrellas, and even plan a beachfront picnic without any last-minute hassle.

Beyond the beaches, Cape Cod offers an abundance of outdoor activities. Bike along the Cape Cod Rail Trail, a scenic path that winds through picturesque towns and woodlands. Take a kayak or paddleboard out on one of the many inlets and bays, where you can explore tranquil waters and spot local wildlife. Whale-watching tours are another must-do, with excursions departing from Provincetown and Barnstable giving you a chance to see majestic whales in their natural habitat. If you love fishing, chartering a boat for a deep-sea fishing trip is an experience that shouldn’t be missed.

Savor the Flavors of Cape Cod

Food is an essential part of any summer vacation, and Cape Cod delivers with some of the freshest seafood and classic coastal cuisine. Lobster rolls, fried clams, and clam chowder are staples that every visitor must try. Planning ahead and making reservations at some of the most popular waterfront restaurants ensures you won’t miss out on these delicious experiences. From casual seafood shacks to fine dining overlooking the ocean, Cape Cod’s dining scene offers something for every taste and occasion.

For those who love a good brew or a craft cocktail, Cape Cod’s breweries and wineries provide the perfect spots to relax and unwind. Spend an afternoon tasting local wines or sampling craft beers at one of the area’s laid-back taprooms. Many spots feature outdoor seating, live music, and beautiful views, creating a perfect setting for a leisurely summer afternoon.

Experience the Cape’s Unique Attractions and Events

Beyond its beaches and seafood, Cape Cod is rich with cultural and historical attractions. Take a ferry to Martha’s Vineyard or Nantucket for a day of island exploration, where you can visit charming boutiques, tour historic lighthouses, and enjoy scenic bike rides. The Cape is also home to fascinating museums, including the Cape Cod Maritime Museum and Heritage Museums & Gardens, which provide insight into the region’s seafaring past and natural beauty.

Summer on Cape Cod is also filled with exciting events, from art festivals and live music performances to farmers’ markets and outdoor movie nights. Planning your trip early allows you to check event calendars and incorporate these unique experiences into your itinerary. Whether you’re interested in an old-fashioned clambake, a scenic sunset cruise, or a lively Fourth of July celebration, Cape Cod has something special for every visitor.

Book Your Summer Vacation on Cape Cod with Pretty Picky Properties

Finding the perfect place to stay is just as important as planning your activities. Pretty Picky Properties offers a wide selection of vacation rentals across Cape Cod, ensuring you have a home base that suits your needs. Whether you’re looking for a waterfront escape, a pet-friendly retreat, or a luxury property with all the amenities, there’s a perfect rental waiting for you. With properties available in Brewster, Dennis, Yarmouth, and beyond, you can stay close to your favorite attractions while enjoying the comforts of home.

Booking early means you get the first pick of the best rentals, ensuring you secure a property that fits your group size and vacation style. Many of these rentals come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces perfect for relaxing after a day of exploring. Whether you want to wake up to ocean views or enjoy a private backyard with a fire pit, planning ahead allows you to find the ideal summer getaway spot.

Start Planning Your Cape Cod Summer Escape Today

A Cape Cod summer vacation is one of the best ways to enjoy sun, sand, and classic New England charm. With a little early planning, you can secure the best accommodations, line up exciting activities, and make restaurant reservations before the summer crowds arrive. Book your dream vacation rental with Pretty Picky Properties today!

Are you wondering where you should celebrate Easter this year? With its charming coastal towns, fresh ocean air, and festive springtime events, Cape Cod is a perfect destination for an Easter getaway. Whether you’re looking for a peaceful retreat by the water, a delicious holiday brunch, or fun-filled activities for the kids, Cape Cod for Easter has something special to offer.

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Easter Egg Hunts and Family Festivities

Easter on Cape Cod is all about family-friendly fun. Towns across the Cape host a variety of Easter egg hunts, making it a perfect destination for kids and families looking for a festive spring break. Places like Chatham, Hyannis, and Dennis put on fantastic egg hunts in local parks and community centers, offering kids the thrill of collecting colorful eggs and prizes. Many of these events also feature visits from the Easter Bunny, live music, face painting, and other entertainment that makes for a fun-filled day.

For a unique twist on the traditional Easter egg hunt, check out the Sandwich Glass Museum’s annual Easter celebration. The museum often hosts glass-blowing demonstrations and special Easter-themed art exhibits, making it a great option for those who appreciate history and craftsmanship.

Easter Brunch on Cape Cod

No Easter celebration is complete without a delicious brunch, and Cape Cod’s restaurants and inns serve up some of the best holiday meals in New England. Many of the Cape’s top dining spots offer special Easter menus featuring fresh seafood, carved meats, and decadent desserts.

The Chatham Bars Inn is known for hosting an elegant Easter brunch with stunning ocean views. Their holiday menu features farm-to-table ingredients, seasonal specialties, and an assortment of mouthwatering desserts. In Hyannis, The Red Jacket Beach Resort also offers a fantastic Easter buffet with classic breakfast favorites and coastal-inspired dishes.

For a more casual setting, many local cafés and bakeries offer delightful Easter morning pastries, including hot cross buns, fruit tarts, and homemade muffins. If you prefer to have a relaxed Easter meal at home, you can even pick up a pre-made feast from one of the Cape’s gourmet markets and enjoy a holiday meal in the comfort of your vacation rental.

Explore the Natural Beauty of Cape Cod

Spring is a wonderful time to experience the natural beauty of Cape Cod. The warmer temperatures and blooming landscapes make it perfect for outdoor adventures. Take a scenic walk along the Cape Cod National Seashore and enjoy breathtaking views of the Atlantic Ocean. The trails at Nickerson State Park in Brewster provide a picturesque setting for a peaceful Easter morning hike.

For those who love biking, the Cape Cod Rail Trail is a fantastic way to explore the region’s charming villages and coastal scenery. The 25-mile trail runs through towns like Orleans, Brewster, and Dennis, offering plenty of opportunities to stop for coffee, take in the views, and soak in the fresh spring air.

If you’re a fan of wildlife, consider visiting the Wellfleet Bay Wildlife Sanctuary, where you can observe birds and other native species in their natural habitats. Spring is a great time to see migratory birds returning to the area, adding another special touch to your Easter getaway.

Book Your Cape Cod Easter Rental with Pretty Picky Properties

A Cape Cod getaway wouldn’t be complete without a comfortable and charming place to stay. Instead of booking a small hotel room, why not enjoy the space and privacy of a vacation rental with Pretty Picky Properties?

At Pretty Picky Properties, we offer a range of beautiful vacation rentals suited for groups of all sizes. Whether you’re visiting with a small group of friends or the entire family, we have the perfect home for you. Our rentals feature fantastic amenities, including pet-friendly options, private pools, waterfront properties, and luxury homes that provide an unforgettable Cape Cod experience.

Lower Cape Vacation Rentals

Our vacation rentals are conveniently located throughout the Cape, including Dennis, Yarmouth, Brewster, and beyond, making it easy for you to explore everything the region has to offer. Whether you’re looking for a cozy home near the beach or a spacious house for a large gathering, Pretty Picky Properties has the ideal rental for your Easter vacation.

Make the Most of Your Cape Cod Easter Getaway

Start planning your Easter 2025 getaway today and book your ideal vacation rental with Pretty Picky Properties. With stunning accommodations and a prime location near Cape Cod’s best attractions, your Easter escape will be filled with relaxation, adventure, and lasting memories.

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Springtime on Cape Cod is a breath of fresh air – literally. The crowds of summer haven’t arrived yet, the flowers are in bloom, and the crisp ocean breeze makes every outdoor activity feel like an adventure. Whether you’re looking to explore nature, enjoy the waterfront, or simply relax in the fresh air, Cape Cod offers plenty of options for a perfect spring getaway. Here are some of the best outdoor activities on Cape Cod to enjoy during this refreshing season.

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Hit the Cape Cod National Seashore

Spring is the perfect time to visit the Cape Cod National Seashore before the summer rush begins. Stretching over 40 miles, this stunning stretch of protected coastline offers hiking trails, picturesque dunes, and some of the most beautiful beaches in New England. Marconi Beach and Race Point Beach are both fantastic spots to take in the scenery, enjoy a quiet picnic, or go for a brisk seaside walk. With fewer people around, you’ll get to experience the natural beauty of the Cape at your own pace.

Cape Cod Dennis

Explore the Cape Cod Rail Trail

Cycling enthusiasts will love the Cape Cod Rail Trail, a 25-mile path that takes you through some of the most scenic areas of the Cape. Running from South Dennis to Wellfleet, this paved trail winds through charming towns, salt marshes, and pine forests, offering plenty of opportunities to stop and explore. Bring your own bike or rent one from a local shop along the way. Spring’s cooler temperatures make it one of the best times of the year to ride.

Take a Whale Watching Tour

Spring marks the return of whales to the waters off Cape Cod, making it an ideal time for a whale-watching tour. Humpback, minke, and finback whales migrate back to the area in the spring, and the waters near Provincetown are one of the best places in the world to see them. Book a tour with a local operator and prepare for an awe-inspiring experience as these majestic creatures breach and play in the Atlantic.

Visit the Cape’s Historic Lighthouses

Cape Cod is home to some of the most iconic lighthouses in New England, and spring is a great time to explore them without the summer crowds. Nauset Light in Eastham, Highland Light in Truro, and Chatham Light in Chatham all offer incredible views and a glimpse into the maritime history of the region. Many lighthouses offer guided tours, so you can learn about their history and significance while enjoying the fresh ocean air.

Go Kayaking or Paddleboarding

The waterways of Cape Cod come alive in the spring, making it the perfect season for kayaking or paddleboarding. Places like Pleasant Bay, Nauset Marsh, and the Bass River provide calm, scenic paddling routes where you can spot wildlife and enjoy the peaceful surroundings. If you don’t have your own gear, rental shops and guided tours are available throughout the Cape to help you get out on the water with ease.

Enjoy a Springtime Stroll Through Cape Cod’s Gardens

Cape Cod’s gardens start blooming in the spring, creating a colorful display of flowers and plants. The Heritage Museums & Gardens in Sandwich is a must-visit spot, featuring 100 acres of lush gardens, walking trails, and beautiful exhibits. The rhododendron and daffodil blooms in spring are truly spectacular. Even just a casual stroll through Cape Cod’s small towns will reveal charming gardens and window boxes filled with fresh spring flowers.

Book Your Spring Rental with Pretty Picky Properties

Spring is a perfect time to unwind and reset, and there’s no better place to do that than in a vacation rental tailored to your needs. We at Pretty Picky Properties offer a range of vacation homes across Cape Cod, including Brewster, Chatham, Orleans, Yarmouth, Dennis, and beyond. Whether you’re looking for a waterfront retreat, a home with beach access, a pet-friendly rental, or a property with a pool, we have something to fit your vacation style. Whether you’re visiting with a small group of friends or bringing the entire family, our properties provide the comfort and amenities you need for a relaxing and memorable stay.

Lower Cape Vacation Rentals

Plan Your Cape Cod Spring Escape Today

Spring is the perfect season to experience the beauty of Cape Cod without the summer crowds. Whether you’re biking the Rail Trail, exploring historic lighthouses, or kayaking through peaceful waters, there’s something for everyone to enjoy. Make the most of your Cape Cod adventure by booking a stay with Pretty Picky Properties, where comfort, convenience, and stunning locations come together to create the ultimate getaway. Browse our selection of vacation rentals today and start planning your spring escape to Cape Cod!

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Spring Break is a time to relax, recharge, and make some great memories, and there’s no better place to do that than beautiful Cape Cod. While many associate Cape Cod with summer, the early spring months offer a peaceful, scenic, and enjoyable way to experience this coastal gem. Whether you’re looking to enjoy outdoor adventures, local cuisine, or just unwind by the water, Cape Cod for spring break has plenty to offer.

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Embrace the Outdoors

One of the best things about Cape Cod is its natural beauty, and during Spring Break, you can fully embrace the great outdoors. Spring on Cape Cod is quieter than the busy summer months, giving you a chance to enjoy the area’s many scenic hiking trails without the crowds.

Take a stroll through Cape Cod National Seashore. This 43,000-acre park offers over 40 miles of pristine beaches, salt marshes, and scenic walking trails. You can walk along the beach, hike through the dunes, or just sit and watch the waves crash against the shore. For those looking for a more challenging hike, the Great Island Trail in Wellfleet is a beautiful, more rugged option, offering views of Cape Cod Bay and the surrounding wilderness.

Even in the spring, Cape Cod’s beaches are a sight to behold. While the water might still be too chilly for swimming, the beaches are perfect for long walks, picnics, or just soaking in the breathtaking views. Nauset Beach in Orleans is known for its expansive shoreline and is a great spot for beachcombing or simply relaxing with a good book.

Explore the Towns and Villages

Cape Cod is made up of charming towns and villages, each with its own unique character. During Spring Break, it’s the perfect time to wander around these quaint communities without the summer crowds.

Start in Hyannis, the commercial heart of Cape Cod. Here you’ll find a variety of restaurants, shops, and cafes to explore. Stop by the Cape Cod Mall or the Main Street area, where you can shop for local artisan goods, Cape Cod-themed souvenirs, and unique treasures. While the weather might not be beach-friendly in early spring, it’s still a great time to enjoy the quaint ambiance of the town.

For a more laid-back vibe, head to Chatham. Known for its charming streets and the iconic Chatham Lighthouse, this town offers a perfect combination of shopping, art galleries, and dining. Explore the quaint Main Street, visit Chatham’s Fish Pier, and grab a bite at one of the cozy restaurants offering fresh seafood.

If you’re looking for something a little more off the beaten path, Brewster is a quieter village that’s perfect for those who want to get away from the crowds. Known for its peaceful beaches and natural beauty, Brewster is the ideal spot to enjoy a relaxing day.

Take a Scenic Boat Tour

While it might be too cold for a swim, a boat tour around Cape Cod is an excellent way to see the beauty of the area from a different perspective. Many local operators offer scenic tours of Cape Cod Bay, where you can enjoy views of the shoreline, wildlife, and historic lighthouses.

In the spring, whale watching is also an option, with several boat tours offering excursions to see migrating whales. Keep an eye out for seals, dolphins, and various seabirds, too!

If you’re looking for something more tranquil, The Cape Cod Canal offers boat rentals where you can enjoy a peaceful ride along the water, taking in the beauty of the surrounding area. Visiting for the Cape Cod Canal Day? Choose our vacation rentals on Cape Cod, Massachusetts and celebrate this day in style!

Relax and Recharge at Your Vacation Rental

After a day of outdoor adventures or exploring the towns of Cape Cod, there’s no better way to unwind than by retreating to a cozy, comfortable vacation rental. And with Pretty Picky Properties, you’re sure to find the perfect spot to make your Cape Cod Spring Break even more special.

We offer a wide selection of beautiful vacation rentals on Cape Cod, including luxury homes, pet-friendly properties, waterfront homes, and rentals with hot tubs. Whether you’re planning a romantic getaway, a family vacation, or a solo retreat, we have something to suit every need.

Eastham vacation rentals

If you’re traveling with family or friends, their spacious homes provide ample room to relax and enjoy quality time together. Many of our homes offer large living areas, fully equipped kitchens, and private outdoor spaces where you can enjoy a barbecue or a relaxing evening under the stars. You’ll also enjoy the convenience of being near popular attractions, with many of the properties located in Dennis, Hyannis, Brewster, Yarmouth, and beyond.

Book with Pretty Picky Properties

When you book a vacation rental with Pretty Picky Properties, you’re setting yourself up for an unforgettable Cape Cod experience. With spacious, fully equipped homes and a range of amenities to suit your needs, you’ll have everything you need for a relaxing and enjoyable stay. Book your stay today and start planning the Spring Break of your dreams on Cape Cod!

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Valentine’s Day is the perfect occasion to show your loved one just how much they mean to you. If you’re looking for a romantic getaway that combines natural beauty, charm, and plenty of opportunities for indulgence, Cape Cod should be at the top of your list. Here’s how you can spoil your loved one on Cape Cod for Valentine’s Day!

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Start the Day with a Cozy Breakfast

Kick off Valentine’s Day with a cozy breakfast. Cape Cod offers plenty of charming spots for a warm and delicious meal, or you can enjoy a homemade breakfast in your rental. If you’re staying in a vacation home, consider preparing something special with fresh local produce, eggs, or seafood. Lobster omelets, fruit salads, or pancakes with maple syrup are all easy ways to add a personal touch and start the day off right.

Stroll Along Scenic Beaches

Cape Cod’s beaches are breathtaking year-round, and Valentine’s Day is no exception. Even in the colder months, a quiet walk along the shore with your partner can feel incredibly romantic. Bundle up in cozy sweaters, hold hands, and enjoy the sound of the waves crashing against the shore as you take in the stunning views of the ocean.

Cape Cod Dennis

For a truly intimate experience, head to one of Cape Cod’s more secluded beaches, where you can enjoy each other’s company without the distractions of crowds. Whether you’re walking along the beach or simply sitting on the sand, this is the perfect place to connect.

Take a Scenic Drive Through the Cape

Cape Cod’s winding roads and coastal landscapes make for the perfect backdrop for a scenic drive. Grab a map or use your phone to find some of the most picturesque spots on the Cape. Take a relaxing drive through charming towns like Brewster, Yarmouth, or Chatham, where you can enjoy beautiful views of the ocean, quaint cottages, and historical landmarks. Stop along the way for some photo opportunities, whether it’s at one of Cape Cod’s iconic lighthouses or in front of a vibrant town square.

Go Wine Tasting or Visit Local Shops

Cape Cod boasts a variety of wineries and local shops perfect for a leisurely afternoon out. Spend some time browsing through artisan shops, galleries, and boutiques where you can pick up a unique piece of Cape Cod to take home. There’s nothing more thoughtful than a handmade gift that captures the essence of your getaway.

For a special treat, consider booking a wine tasting experience at one of the local wineries. Many offer cozy settings with beautiful vineyard views, perfect for sharing a glass of wine with your loved one. Whether you prefer a dry red or a crisp white, you’ll enjoy tasting the local flavors while spending quality time together.

Unwind with a Spa Day

Valentine’s Day is all about relaxation, and what better way to unwind than with a rejuvenating spa day? Cape Cod offers several spas and wellness centers that specialize in couples’ treatments, including massages, facials, and more. Book a couple’s massage where you can both relax side by side, letting go of any stress and embracing the peaceful atmosphere.

Many of the spas also offer specialty Valentine’s Day packages, such as champagne and chocolate treatments, which add a little extra indulgence to your day.

Find Your Cape Cod Valentine’s Day Rental with Pretty Picky Properties

The key to a truly unforgettable Valentine’s Day getaway is where you stay. Instead of booking a typical hotel room, why not rent a private home or cottage where you and your loved one can enjoy some privacy and comfort? Pretty Picky Properties offers a large selection of vacation rentals across Cape Cod, including Yarmouth, Brewster, and beyond.

With Pretty Picky Properties, you can find the perfect home that suits your romantic escape, whether it’s a cozy cottage or a luxurious beachfront property. Our homes come with a range of amenities designed to make your stay as relaxing and enjoyable as possible. You can choose from properties that are pet-friendly, or even luxury options with stunning views. Each property is carefully curated to ensure a high standard of comfort and charm, making it the ideal place to enjoy your romantic Valentine’s Day getaway.

Start Planning Your Romantic Getaway

Cape Cod is the ultimate destination to spoil your loved one this Valentine’s Day. From scenic beach walks and cozy breakfasts to spa treatments and sunset cruises, there’s no shortage of romantic activities to enjoy. Contact us to book your romantic escape today and make this Valentine’s Day one to remember.

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If you’re planning a trip to the stunning beaches of Cape Cod, 2025 is the perfect year to take advantage of Book Direct Day, happening on February 5th! Whether you’re visiting to explore the charming towns, enjoy the incredible seafood, or just relax by the water, you can make the most of your vacation by booking directly with property owners and managers. Discover why booking direct is the way to go for your Cape Cod getaway!

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The Benefits of Booking Direct on Book Direct Day

Booking directly with a vacation rental property has its perks, and Book Direct Day is a great reminder of all the advantages it offers. One of the biggest draws of booking direct is the cost savings. When you book through third-party websites like Airbnb or Vrbo, you’re often hit with hidden fees and service charges that can add a significant amount to your total bill, usually 10%-15%. These fees, though convenient for the platform, don’t benefit you as the guest or the property owner.

By booking directly through a property management team or individual owner, you can avoid those pesky third-party commissions and fees. That means more of your money goes to your vacation instead of to the platform. In fact, many property managers offer exclusive discounts, special packages, or lower rates for guests who book directly. So not only can you save money by booking direct, but you can also often get a better deal than you would on a third-party site.

Better Communication Means a Better Stay

Booking directly gives you the opportunity to communicate personally with the property manager, which leads to a more customized and personalized experience. Have a special request? Need an early check-in or late check-out? Want to add something extra to your stay, like arranging a surprise welcome basket or special accommodations for your pet? When you book through a third-party platform, all communication is filtered through the platform, which can sometimes slow down the process or limit the flexibility of what’s possible.

When you book directly, you have direct access to our team, meaning any special requests, questions, or concerns can be addressed quickly and efficiently. Whether it’s finding the perfect property for your family, customizing your experience with local recommendations, or ensuring you have everything you need for a stress-free stay, booking direct allows you to get the most out of your trip.

A Stay Tailored Just for You

One of the biggest advantages of booking directly with property managers is the flexibility and customization that it offers. Booking platforms like Airbnb or Vrbo often follow a rigid set of guidelines when it comes to your stay, such as check-in times, room selection, cancellation policies, and so on. While these policies might work for some, they don’t always provide the freedom to cater to your personal needs.

When you book directly, the experience becomes much more flexible and customizable. You’ll have the opportunity to speak directly with the property manager to request changes or special accommodations, such as a late check-out, a different room layout, or even specific amenities that suit your trip’s purpose.

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Cape Cod Rental Home

Perks for Returning Guests

If you plan to make Cape Cod a regular vacation destination, you’ll want to take advantage of the loyalty rewards that many property managers offer to repeat guests. By booking directly, you can often receive exclusive perks for your return visit, including discounts, free upgrades, or even additional amenities that are available only to loyal customers. These rewards are a great way to feel valued and appreciated as a guest, and they can make your future visits to Cape Cod even more special.

Support Local Businesses and the Cape Cod Economy

When you choose to book directly with a local business like Pretty Picky Properties, you’re supporting small businesses and contributing to the local economy. Large third-party platforms often take a substantial cut of the booking fee, meaning much of your payment goes to the platform, not to the local property owners who are working hard to maintain their vacation rentals. By booking directly, more of your money stays in the local community, helping to support the Cape Cod economy and the people who make it such a wonderful place to visit.

Book Your Stay with Pretty Picky Properties

If you’re looking for a Cape Cod vacation experience that’s more personal, more affordable, and more memorable, look no further than Pretty Picky Properties. We offer a wide range of beautiful vacation rentals across Cape Cod, including Brewster, Yarmouth, Dennis, Chatham, Eastham and beyond.

Looking to head up north? Check out our Wellfleet vacation rentals! Whether you’re visiting for a solo retreat, a romantic couples getaway, or a family vacation, we have a property that will put a smile on your face.

Our vacation rentals are designed with comfort and style in mind, offering everything you need for the perfect getaway. From luxurious amenities like private pools and hot tubs to pet-friendly properties and last-minute availability, we’ve got you covered. And since we specialize in properties with water views and close proximity to Cape Cod’s best beaches, you can enjoy all that the area has to offer without venturing too far from your rental.

Plan Your Perfect Cape Cod Getaway

As you plan your 2025 Cape Cod adventure, remember that booking directly has so many benefits that can enhance your stay. From the cost savings and flexibility to personalized communication and the satisfaction of supporting local businesses, booking with Pretty Picky Properties is the smart choice for your Cape Cod vacation. Book your stay today and get ready to enjoy the perfect Cape Cod getaway!

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The new year is a time for fresh starts and bold resolutions, so why not make yours the promise of adventure and relaxation? Cape Cod, Massachusetts is a dream destination that offers the perfect combination of natural beauty, charming towns, and exciting activities to help you start 2025 on a high note. Whether you’re looking for a romantic getaway, a family vacation, or a solo retreat, Cape Cod for New Year’s is a destination for anyone.

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A Bucket-List Destination

Cape Cod is a destination that feels like stepping into a postcard. With its iconic lighthouses, stunning beaches, and quaint villages, it has a timeless appeal that draws visitors year after year. But beyond its picturesque charm, Cape Cod offers a wide range of activities and experiences for travelers of all ages and interests.

Outdoor enthusiasts can explore Cape Cod’s miles of sandy beaches, scenic biking trails, and lush nature preserves. Food lovers will delight in the area’s fresh seafood and farm-to-table dining options. History buffs can explore the Cape’s rich maritime heritage through its many museums and historical sites. No matter what kind of traveler you are, Cape Cod offers something special to discover.

last minute vacation cape cod

When Is the Best Time to Visit Cape Cod?

While Cape Cod is a popular summer destination, each season brings its own unique charm. If your 2025 resolution includes fewer crowds and a slower pace, consider visiting in the spring or fall. In spring, the Cape comes alive with blooming flowers and migratory birds, offering mild temperatures and ideal conditions for outdoor adventures.

Fall is equally magical, with crisp air, golden foliage, and quieter beaches. It’s also a great time for foodies, as the Cape’s local seafood shines during harvest season. Summer, of course, remains the peak season for a reason. It’s when the Cape is buzzing with festivals, outdoor concerts, and lively beach days. No matter when you choose to visit, Cape Cod promises a memorable experience.

What Cape Cod Offers Travelers

Cape Cod is the perfect destination for relaxation and exploration. Begin your mornings with a walk along the beach, watching the sunrise over the Atlantic Ocean. Spend your afternoons biking along the Cape Cod Rail Trail, a scenic 25-mile route that winds through quaint villages and wooded areas. The trail is family-friendly, making it a wonderful activity for groups of all ages.

For those who love the water, Cape Cod offers fantastic fishing, kayaking, paddleboarding, and even whale-watching tours during the warmer months. Visiting in the fall or winter? Bundle up and explore the Cape’s many hiking trails, like those at the Wellfleet Bay Wildlife Sanctuary, where stunning views and peaceful settings abound.

Cape Cod’s vibrant towns also offer unique shopping experiences. From antique shops in Sandwich to art galleries in Provincetown, you’ll find treasures to bring home as a reminder of your trip. End your days with fresh seafood at one of the Cape’s celebrated dining spots. Lobster rolls, clam chowder, and oysters are local specialties you won’t want to miss.

Your Home Away from Home with Pretty Picky Properties

One of the best ways to experience Cape Cod is by staying in a vacation rental that feels like your own private retreat. With Pretty Picky Properties, you’ll find a stunning selection of homes across Cape Cod’s most desirable communities, including Chatham, Orleans, Wellfleet, and Yarmouth.

Our rentals are designed to suit a variety of travel styles and group sizes. Looking for a luxury waterfront home? We’ve got you covered. Traveling with a pet? Check out our pet-friendly rentals that welcome every member of the family. Dreaming of a house with a private pool? You’ll find it in our portfolio.

Each property is thoughtfully furnished and equipped with amenities like fully equipped kitchens, spacious living areas, and outdoor spaces perfect for relaxing or entertaining. Staying in a vacation rental also allows you to cook your own meals, offering a convenient way to save money while enjoying quality time with loved ones.

With Pretty Picky Properties, you’ll have a home base that makes exploring Cape Cod seamless and enjoyable.

Plan Your Cape Cod New Year’s Escape Today

Cape Cod is calling, and there’s no better time to answer than 2025. Whether you’re looking to relax by the ocean, explore charming villages, or savor the freshest seafood around, this timeless destination has something for everyone.

Book your Cape Cod vacation rental with Pretty Picky Properties today and start planning your perfect getaway. With stunning homes, exceptional service, and all the beauty of Cape Cod waiting for you, your New Year’s resolution is about to become your favorite adventure yet.

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A Cape Cod vacation is destined to be one of the greatest vacation you have ever taken, no matter which community, town, or village you choose to stay in, but there are ones that we at Pretty Picky Properties believe will truly enhance your vacation experience. The sun appears to shine brighter, the beaches seem warmer and more welcoming, and because we refuse to offer anything less than the best for our guests, you will find our Cape Cod vacation retreats luxuriously residing within the city limits. This guide to the top Cape Cod communities will give you a better idea of what to expect and help you to narrow down your final destination to the community that best fits your family’s needs.

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Barnstable, Founded in 1639

Barnstable is one of the oldest communities on Cape Cod, steeped in history and offering seven charming villages, many of which we will be discussing further down the page. Home to the Olde Colonial Courthouse built in 1774, making it one of the oldest Colonial buildings in the country, the rich history, stunning views, and natural landscape will ensure that there is always something wonderful to do or see without having to travel far. The best time to visit is (and this will pretty much stay the same for all communities unless otherwise noted) in the months of May, June, September, and October, as the weather will be wonderful, and the crowds will be smaller. We like to call it “Locals Summer”. Below, we have listed some of our favorite Barnstable activities, attractions, and restaurants.

Sandy Neck Beach Park

Offering a 6.5-mile-long barrier beach with dunes that can reach up to 100 feet tall, Sandy Neck Beach Park is popular with hikers, bird watchers, swimmers, and drivers, as the beach can be driven on with offroad vehicles with the proper permit.

Cape Cod Barnstable

Barnstable Comedy Club, 3171 Main Street

Barnstable’s long history means it features a lot of “the oldest” businesses, buildings, etc., and the Barnstable Comedy Club falls under the category of the oldest club in the area. Continually open for over 100 years, talented performers have helped guests lose themselves in the magic on the stage, and that magic continues today.

The Dolphin Restaurant, 3250 Main Street

There’s a reason long running restaurants last, and that reason is a complicated blend of staff, ambience, and of course, good food. The Dolphin Restaurant, in business for over 70 years, is the perfect example. Moderately priced and offering a menu filled with both surf and turf options, we have visited many times over the years and never had a bad experience. Seafood on Cape Cod is fresher and sweeter than what you may be used to, so if you are choosing between a burger and their shrimp and scallops, go for the latter. You can thank us later!

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Brewster, Founded in 1803

Brewster is one of the newer Cape Cod areas founded in 1803. It was originally settled in the mid-1600s. Brewster is home to the largest pond on Cape Cod, coincidentally named Long Pond, and is nicknamed the Sea Captain’s Town due to the large number of sea captains who once settled there.

Brewster General Store, 1935 Main Street

Shopping is a popular activity during any vacation, and there is a large selection of stores in the area that we highly recommend, but perhaps the most fascinating one is the Brewster General Store. The building in which the store is housed was originally a church, but in 1866 it was converted into a general store and has been a primary source of candy, gifts, toys, and yummy ice cream ever since.

Cape Cod Brewster

Stony Brook Grist Mill, 830 Stony Brook Road

Originally built in 1699, the grist mill was washed away in a storm. It was rebuilt on the same site in 1751 using beams from the original building. During the Revolutionary War, grains from the mill were taken to feed British soldiers, and today it is the last remaining building of Factory Village, a once thriving industrial part of Brewster. Open for tours on weekends during the spring and summer months, cornmeal is still made and sold at the mill, providing a unique souvenir for your travels.

Spinnaker Restaurant, 2019 Main Street

Reservations are required for Spinnaker Restaurant, one of our favorite Brewster special occasion eateries. The menu changes on a regular basis, and with each new rendition we grow to love it more, recommending that guests save room for dessert—in particular the chocolate dessert of the day!

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Chatham, Incorporated in 1712

Although it wasn’t incorporated until 1712, Chatham was originally settled in 1685. Its charm and beauty stand out in the Cape Cod communities in that is renowned for both, so be sure to keep your camera handy when visiting.

Chatham Lighthouse, 37 Main Street

Constructed in 1808, the Chatham Lighthouse still shines its light over stormy waters today and during the season (July through September). Operating 24 hours a day, it stands 48 feet tall, and fortunately for tired travelers, it takes only 44 steps to reach the top.

Cape Cod Brewster

Ducks in the Window, 507 Main Street

One of the quirkier stores on Cape Cod, Ducks in the Window is loved by all, as its shelves are filled with rubber ducks of all sizes and professions. Yes, we said professions, as there are police ducks, nurse ducks, even teacher ducks, and you can’t help but smile and be happy when you walk into the store for the first time.

The Chatham Squire, 487 Main Street

The Chatham Squire is a typical New England restaurant, featuring casual décor, a great bar, and good food that sticks to your ribs as you go about your touristy business. The bar side offers video games and foosball, while the dining side is a little more formal, providing a menu filled with seafood delights you will greatly miss when it is time to leave Cape Cod. Meet me at the Squire!

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Dennis, Settled in 1639, Incorporated in 1793

The history of Dennis makes it a popular vacation destination for history buffs, offering a large variety of historic neighborhoods that visitors simply love to stroll about in.

The Cape Playhouse, 820 Main Street

Professional summer theater isn’t as big of a deal on the mainland as it once was, but on Cape Cod, it is integral to the Cape Cod experience, and the Cape Playhouse has been continuously running since 1927. Famous for Humphrey Bogart performing on its stage, you will feel a sense of history as you sit in the audience, perhaps imagining what it would have been like to watch the talented Humphrey Bogart performing.

Cape Cod Dennis

All American Town of Dennis Fireworks

The end of summer is always a sad time for Cape Cod, but the party that sends off our guests with a bang is something to look forward to. Featuring a Hallmark movie style bonfire on the West Dennis Beach, there will be live music, the opportunity to roast marshmallows, and the big burst of colorful explosions in the sky, all guaranteed to make this farewell to summer shine a little brighter.

Grumpy’s, 1408 Main Street in East Dennis

Breakfast is the most important meal of the day, and when you enjoy it at Grumpy’s, we can promise you won’t leave grumpy or unsatisfied. Grumpy’s selection of benedicts boggles the mind, and if you are here long enough, you may want to work your way through each dish.

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Harwich, Founded in 1665 and Incorporated in 1694

Cranberry bogs have been a huge part of Cape Cod for over 200 years, with Harwich being the town most commonly associated with the colorful fruit. Harwich has been named as America’s second happiest seaside town.

The Harwich Cranberry Arts & Music Festival, Weekends in September

One of our favorite local festivals, the Harwich Cranberry Arts & Music Festival pays homage to the cranberry with food trucks, live music, and a wooden dance floor in a tent, as well as over 150 craft vendors selling jewelry, art, gifts, and handmade foods. The best way to get to know the area you are visiting is by attending its local festivals, and this end of season festival will bring you joy.

Cape Cod Harwich

Watch the Harwich Mariners Win a Game

The Cape Cod Baseball League is where tomorrow’s superstars perfect their game, with some of the MLB’s biggest players having hit a homerun with their traditional wooden bats. Thurman Munson, Jason Varitek, Aaron Judge, and many, many more have played on these hallowed fields, and who knows? Maybe the players you are watching today will be tomorrow’s superstars.

Cape Sea Grille, 31 Sea Street in Harwich Port

Housed inside a former sea captain’s home, Cape Sea Grille is a wonderful special occasion spot serving new American cuisine. Open year round and offering elevated selections of surf or turf meals, their braised pork Osso Busco is a dish dreams are made of.

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Hyannis Port, Founded in 1639

Hyannis Port has a long history, but perhaps its most famed time were the years the Kennedys made the village their playground. The Kennedy compound has been the summer home for the Kennedys since the 1920s, when Joseph Kennedy first rented the initial cottage for a summer vacation. The family still owns the compound, and the widow of Robert F. Kennedy actually lived there until her death in October of 2024.

John F. Kennedy Hyannis Museum, 397 Main Street in Hyannis

The Kennedy name was much loved in this part of Cape Cod, on all of Cape Cod, and the JFK Hyannis Museum pays proper homage to the hero whose life was cut too short. Hyannis Port was always considered the heart and home of the Kennedys, and the museum doesn’t stop at chronicling JFK’s life but touches on all the Kennedys who lived and loved here through the years.

Cape Cod Hyannis Port

Baxter’s Wharf Restaurant & Waterfront Dining, 177 Pleasant Street in Hyannis

We can’t help but focus on the Kennedys when discussing Hyannis Port, and we aren’t going to stop with the restaurant suggestion. Baxter’s Wharf Restaurant was known to be where the Kennedys ate often, and if you had visited during that time, chances are you may have dined in the same room as the President, his brother, or any of the numerous family members who made Cape Cod their home in the summer months.

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Orleans, Settled in 1693

Orleans is the only US site attacked during WWII, when a German U-boat fired at the tug, Perth Amboy. Today, it is known for its beautiful landscape, arts scene, and its history that began long before the U-boat incident, an incident that Disney made a movie about in 2016.

Jonathan Young Windmill, 41 Old Kings Highway in Orleans

Most people do not know that there are seven windmills on Cape Cod, with the Jonathan Young Windmill being built in the early 18th century. It is a unique part of our history, still offering original parts that actually work. Open to the public in July and August, the windmill took a circuitous route to get to where it stands today, having been built in South Orleans, moved to the center of town, then to Hyannisport, then returned to its current location.

Cape Cod Orleans

The Alley Bowling & BBQ, 191 MA-6 in Orleans

Combining the fun of candlepin bowling and the yum of house smoked barbecue, the Alley Bowling & BBQ may be your favorite Cape Cod experience of all. Candlepin bowling is played with smaller balls and thinner pins and is a sport that originated right here in New England. Barbecue may not be a food that is unique to Cape Cod, but we assure you that you will find no beef with their beef!

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We Are There

The best communities of Cape Cod have one major thing in common: our Pretty Picky Properties are located in each and every one! Offering comfort, style, and a quiet New England luxury, our properties will become an integral part of your vacation experience. Reserve your favorite today!

Once upon a time, Sundays were set aside to spend time with extended family. Sunday dinners at grandma’s house were common activities. We played with cousins who would always be considered our first friends, ate homemade meals that the diet police would not approve of, and savored the familiarity of family. Times have changed, and those special moments don’t happen very often, making family reunions a vital way of keeping the family close, and when you really want to make the family reunion special, choosing to take it on the road to Cape Cod is a great idea. Choosing Pretty Picky Properties for your vacation accommodations is an even better one, as these 10 reasons to plan your family reunion on Cape Cod will show!

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Reason #10: You Have Always Wanted to Visit Cape Cod

Sometimes the simplest reasons are the most compelling ones, and wanting to visit Cape Cod can be the best reason of all to plan your family reunion there. You’ve been dreaming about it for years, saving your pennies so you can afford to do it right, and now it is time for your vacation dreams to come true. Cape Cod has been a much-loved vacation destination for over 100 years, and we can guarantee that you aren’t the only one in your family that has dreamed about visiting, ensuring that other vacation dreams will come true as well. Welcoming families with charm, history, and a variety of ways to play together or separately, your family reunion on Cape Cod will be one that is never forgotten.

Cape Cod Visit

Reason #9: A Beach Vacation Is an American Tradition

A family vacation at the beach is a long-standing tradition that is also one of life’s greatest luxuries, and when you get to share that same vacation with your extended family, it elevates the experience exponentially. As mentioned earlier, your cousins were your first friends, but are your children’s cousins theirs? Chances are they only get together for funerals and family reunions, making your family vacation to Cape Cod vital in helping them forge deeper bonds. Many of our Pretty Picky Properties are located on or near the Cape Cod National Seashore, and the cousins can work on building their bonds as they work together to build sandcastles at shore’s edge. Renting a boat and towing the squealing youngsters on rafts or innertubes will be another bond tightening experience and because our homes offer entertainment options as well as comfort and luxury, they can also work to put together large puzzles throughout their stay. And as you hang out with your own parents, grandparents, and cousins, reminiscing about the crazy times you and your cousins shared during your growing up years will help you rebuild yours.

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Reason #8: Educational and Entertaining

As parents, we want our children to do well in a world that doesn’t always make it easy to do so, and part of helping to ensure that they do can be accomplished by education. On the plus side, every experience can be a lesson learned, but on the negative side, our children often fail to see the fun or importance. And so, just like we hide pills in treats for our dogs, we hide education in entertainment, taking them to science museums where interactive activities are fun and attention grabbing. On Cape Cod, history surrounds you and even as the adults in your group appreciate walking in the footsteps of our ancestors, your children may just think its “cool” exploring some of the more historical spots, spots that will unbeknownst to them offer a history lesson they will enjoy.

Cape Cod Educational

Hoxie House, 18 Water Street in Sandwich

Reputed to be one of the oldest houses on Cape Cod, Hoxie House was built circa 1640, over 100 years before our nation fought for its independence, and the tours offered of this ancient home will give guests a fascinating peek into that time period. Holding what may be the oldest surviving loom in America and serving as a meeting place for Reverend John Smith, the artifacts from colonial times will surprise your kids due to their simplicity.

Whydah Pirates Museum, 674 MA-28 in West Yarmouth

There is absolutely no doubt in our minds that everyone in your family will be fascinated by the Whydah Pirates Museum. The artifacts displayed in this museum were recovered from an 18th century ship used for piracy, and the replica of a pirate ship that can be found here will capture the imagination of your youngest family members. Inexpensive, (admittance fees run between $14 and $16) the history lessons learned from the museum will never be recognized as lessons at all.

Cape Cod Pirates

Reason #7: The Perfect Backdrop for Family Photos

Just as the weekly family dinner has gone by the wayside, so have family pictures, and if you are like us, the last family picture taken may be missing the newest additions to the family. A family reunion on Cape Cod, however, offers the perfect backdrops for taking updated pics that the matriarch will cry over when she sees them. We’ve listed some of our favorite spots for taking family photos below.

Mayflower Beach in Dennis

Countless family photos have been taken at the beaches of Cape Cod over the past two centuries, and any beach on the Cape will work as a backdrop, but Mayflower Beach offers miles of flats and wavy patterns in the sand that will add interest to your picture. Don matching attire (white shirts and blue jeans are the most common clothing worn in family beach pictures) and head to the beach at sunset, taking pictures filled with color and serenity, and of course, all of your favorite people.

Cape Cod Beach

Chatham Lighthouse in Chatham

The lighthouses of Cape Cod have served as backdrops for pictures for as long as we can remember, and although the Nauset Lighthouse, the one pictured on the bag of Cape Cod Potato Chips, may be the most well-known lighthouse, the Chatham Lighthouse is one that we feel offers the most charm. Standing tall and proud as it does its duty of protecting the ships in the area from harm, the lighthouse keeper’s home and its red roof add an extra element of wow to any photos taken here!

Reason #6: Activities for Large Groups

The problem with traveling with large groups lies solely in the realization that there may not be many activities the group can participate in together. Beach days, of course, are always an option on Cape Cod, but there are many other activities that large groups can partake in during a family vacation to Cape Cod, some of which are listed below.

Cape Cod Beach

Cape Cod Harbor Tour, 715 Main Street in Harwich Port

A sunset cruise is a traditional Cape Cod adventure, one that you may not think you can participate in when you are traveling with a large group, but Cape Cod Harbor Tour’s newest boat, the White Shark, offers room for up to 45 guests, and their sunset cocktail cruise promises to be an adventure your entire family will enjoy. The kids can sip soft drinks as they eat their ice cream, but the cash bar offering cocktails, local wines, beer, and snacks ensures that you will be comfortably happy as you and your large group watch the sun fall into the sea.

Hiking

The natural landscape of Cape Cod will make you want to spend as much time as possible outside playing, something that is easy for larger groups to do. There are many different hiking trails that traverse the cape, offering a wonderful way to learn the beauty of the area. Gray’s Beach Boardwalk in Yarmouth Port offers a quick family friendly hike that is accessible for hikers of all ages and skill levels, extending out over the marsh and offering views of the landscape, the sea, and all its inhabitants that will change the feel of your family reunion getaway.

Cape Cod Hiking

Reason #5: The Cape Cod Rail Trail

Another popular group activity is a ride along the Cape Cod Rail Trail, extending out 26 miles and passing through six different Cape Cod towns, most of which you will find Pretty Picky Properties located in. Following alongside the old railroad tracks that used to bring tourists and supplies to various towns throughout Cape Cod, riders can rent bikes from a variety of shops, most of which are located on or near the trail. Passing through the towns of Yarmouth, Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet, the changing land and seascape never fails to fascinate. The Rail Trail Bike & Kayak Rentals, 302 Underpass Road in Brewster, offers a large selection of bike and bike gear rentals as well as providing direct access to the trail.

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Reason #4: Restaurants that can Handle Large Groups

Our Pretty Picky Properties retreats feature large and fully equipped kitchens that will make meal prep fun and easy, but you don’t want to be stuck at home creating every meal, especially as the restaurants of Cape Cod offer delicious meals that are prepared, served, and cleared away by someone other than you!

Cape Cod Food

Freeman’s Grill, 1000 Freeman’s Way in Brewster

Located on the Captain’s Golf Course and offering all the space you need for a large group seeking sustenance and suds, Freeman’s Grill in Brewster is destined to be your favorite dining spot when hitting the town.

The Skipper Restaurant & Chowder House, 152 S Shore Drive in South Yarmouth

Open seasonally, the Skipper Restaurant & Chowder House is a Cape Cod tradition, one that you can experience with your large group. One of the oldest restaurants on the Cape, the views of Nantucket Sound will make the perfect accompaniment to your seafood dinner and Skipper’s Ice Cream Shack will make the perfect ending to a beautiful meal with family.

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Reason #3: The Family That Fishes Together Eats Well

There is nothing like a fish dinner caught and grilled yourself, and when the family joins in the fun, the quiet hours between bites are destined to be filled with laughter and fish stories about the ones that got away. (They weren’t there, so how would they know?) And although you are perfectly capable of renting a boat and heading out blindly to spots where you can drop a line and cross your fingers, hoping for a bite or three, or you could hire a charter, one in which the captains know all the hopping spots, practically guaranteeing you will catch your limit. If the latter sounds best to you, Cape Cod Family Charters, 200 Millway in Barnstable is, of course, the only charter company we would recommend for your family fishing adventures. Offering 4-, 5-, or 6-hour expeditions, the captains will take your family out to catch a boat load (Is that where the term came from?) of striped bass, bluefish, tuna, and cod, and at trip’s end, will take the obligatory picture of your haul, which of course you can share on social media, earning the envy of all your friends back home.

Cape Cod Fishing

Reason #2: Tour of Lighthouses

Did you know that there are 14 lighthouses on Cape Cod, including Chatham Lighthouse, where you took your family photo, and Nauset Lighthouse, which you have been seeing on the bag of your favorite Cape Cod Potato Chips for years. No trip to Cape Cod would be complete without a visit to at least one of the lighthouses, taking the tours and climbing all the stairs, but if you really want to show off, you can visit them all. Highland Lighthouse is a bit of a drive, being located in North Truro, but as it the oldest and tallest lighthouse on Cape Cod and was commissioned by George Washington himself in 1797, it definitely is worth the little extra effort!

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Reason #1: Our Pretty Picky Properties Make Luxurious and Spacious Accommodations

Cape Cod Rental Home

Pretty Picky Properties is named as such due to the fact that we are pretty picky about the properties we offer, which means your family reunion vacation is that much more comfortable and luxurious. Our largest homes offer as many as 10 bedrooms and room for 20 to 24 people while also providing a large selection of luxury amenities that can include private swimming pools, hot tubs, and game rooms that will encourage your loving family to stay home and play on days when everyone is feeling especially comfy! Firepits and outdoor kitchens will entice you to engage in family barbecues and storytelling sessions that last long into the night, and large porches lined with rockers will be where everyone sits to watch the sun set every evening of their stay. Check out our 8-bedroom Cape Cod mansion rentals that include ample private space for everyone!

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Your family reunion on Cape Cod is destined to be one you never forget when you choose our Pretty Picky Properties family retreats. Reserve your favorite property today!

Looking for a refreshing and unique way to kick off the New Year? Trade the hustle and bustle of crowded city celebrations for the charm of Cape Cod. This quintessential New England destination might be famous for its summer vibes, but the Cape has plenty of magic to offer in winter, especially during New Year’s. From cozy celebrations to crisp seaside walks and local festivities, a Cape Cod New Year’s trip is the perfect mix of relaxation and adventure.

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Cape Cod Dennis

Cozy Up to New England Charm

Cape Cod in winter has a special kind of magic. The crowds are gone, and the charming towns are beautifully peaceful, with twinkling lights and that quintessential coastal coziness. Picture yourself strolling along historic Main Streets in towns like Chatham or Provincetown, bundled up with a warm drink in hand, as you pop into quaint shops and admire the festive window displays.

While you’re there, stop by local bakeries and cafes for treats like fresh-baked pastries or a cup of clam chowder to warm your soul. Many shops and restaurants remain open year-round, and you’ll love the slower pace and welcoming atmosphere that Cape Cod is famous for.

Cape Cod New Year’s Eve Festivities

If you’re looking for festive ways to celebrate New Year’s Eve on the Cape, there are plenty of fun options to explore!

One of the highlights is First Night Chatham, an annual celebration that transforms the town into a family-friendly New Year’s wonderland. With ice sculptures, live music, kids’ activities, and a magical early countdown for the little ones, it’s a great way to enjoy the holiday. The evening wraps up with a festive fireworks display over Oyster Pond, what better way to kick off the New Year?

New Years in Cape Cod

If you’re in the mood for something a bit more relaxed, many local restaurants host special New Year’s Eve dinners. Book a cozy table at spots like The Red Inn in Provincetown or The Ocean House in Dennis, where you can enjoy fresh seafood, gourmet dishes, and celebratory cocktails.

Explore Cape Cod’s Natural Beauty

Cape Cod’s beauty isn’t limited to summer, its coastal charm is just as breathtaking in winter. Bundle up and explore the Cape’s natural wonders with fewer crowds and plenty of room to roam.

Take a brisk walk along the beach at Cape Cod National Seashore or visit the picturesque dunes in Wellfleet. The views are stunning, and the fresh sea air is the perfect way to reset after the holiday hustle. For a dose of wildlife, head to Monomoy National Wildlife Refuge in Chatham, where you might spot seals lounging along the shore.

Don’t forget to check out the Cape Cod Rail Trail for a peaceful winter hike or bike ride. This 25-mile path winds through charming towns, forests, and cranberry bogs, offering a unique perspective of the Cape’s winter beauty.

Celebrate at Your Cape Cod Vacation Rental

One of the best parts of spending Cape Cod New Year’s? You don’t need to go out to have an amazing time. In fact, some of the most memorable celebrations happen in the comfort of your vacation rental.

Many Cape Cod rentals offer cozy gas fireplaces, game rooms, and stunning views – perfect for a quiet evening or an intimate gathering. Plus, if you’re feeling festive, host your own countdown with a homemade dinner featuring local seafood (think lobster rolls or fresh oysters), pop some champagne, and enjoy the magic of New Year’s in a space that feels like home. Whether it’s relaxing in a spacious living room or watching the ball drop from your rental’s private deck, the possibilities are endless.

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Stay with Pretty Picky Properties

Ready to plan your New Year’s trip to Cape Cod? At Pretty Picky Properties, we make it easy to find the perfect rental for your celebration. Whether you’re planning a quiet getaway or a lively family gathering, we have a variety of properties to suit every traveler and group size.

Many of our properties are pet-friendly, so you can even bring your furry friends along for the fun! From charming cottages to luxurious waterfront homes, there’s something for everyone.

Our rentals are conveniently located in some of Cape Cod’s most beloved towns, including Brewster, Chatham, Wellfleet, Yarmouth, and Dennis. No matter where you stay, you’ll be close to the area’s best attractions, restaurants, and natural beauty.

Make Your New Year’s Magical

Book your New Year’s adventure with Pretty Picky Properties today and get ready to experience the magic of Cape Cod this holiday season. Here’s to a New Year filled with joy, laughter, and unforgettable memories!

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