The next time you need a break, head to a place that boasts plenty of New England and small-town charm. If you’re also looking for a stay in a small waterfront town, consider Osterville. When planning your retreat, book private Osterville vacation rentals with Pretty Picky Properties. Ask about our pet-friendly properties so your furry family members can join you on your Osterville vacation, too!
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When you vacation on Cape Cod and Osterville, the beautiful seashore, rich history, and small-town charm of each town are enough to keep everyone busy throughout the stay. Take part in beach activities like swimming, sandcastle building, and sunbathing. Pack a beach picnic or plant your beach umbrella and beach chair and read with the sound of the waves in the background. Learn about the town’s history at the Osterville Historical Society Museum and stop in at the Crosby boat building shop – the oldest currently active boat shop in operation. Escape to the serenity of the Skunknett River Wildlife Sanctuary or learn a new skill at Stand Up & Paddle Cape Cod. Make sure you stop in at Osterville Mercantile and pick up books, décor, gifts, toys, clothing, and more to remember your trip.
Open the door to the “indoor” side of Osterville when you arrive at your Osterville Cape Cod rentals provided by Pretty Picky Properties. Step into the open great room featuring beautiful and stylish furnishings with touches of New England and beach charm, all waiting to host you for plenty of rest and relaxation wherever you please. Our spacious great rooms easily combine the daily indoor functions of living, cooking, and dining, bringing everyone together for meals and other daily activities throughout your vacation. Lounge in comfortable and cozy living spaces where you can stretch out and relax after a day at the beach or enjoying other outdoor New England fun. You may also choose to gather together for a favorite movie or show on a flat screen TV. You can even choose a movie from the provided movie library of DVDs or Blu Ray discs in select rentals. Take a seat on a comfortable couch or chair and gather everyone in one place to plan the day together before heading out on adventure.
At mealtime, make use of the fully equipped kitchen that can handle all your cooking and dining needs during your Osterville retreat. Prepare delicious home-cooked meals or New England favorites with the help of sprawling counters, including kitchen islands in select units. A myriad of cabinets and drawers are packed with everything you’ll need. We round out the space with modern appliances to prepare it all, so you’ll never miss making your favorite meals each day. Serve the meal in a dining space featuring a table that seats the entire group for a fun and relaxing group meal, anytime.
The comforts and conveniences of home start before you even set foot inside the home. Each of our Osterville vacation rental homes boasts laundry rooms, so you can pack light and save space for fun souvenirs from your Cape Cod adventures. Full-size washers and dryers mean everyone has clean clothes for the duration of the trip – without the need to search and pay for expensive laundromats or laundry services.
Take advantage of another important convenience you may need on vacation: free and private Wi-Fi connection. You’ll be able to stream favorite movies and TV shows, keep loved ones in the loop with pics and video on social media, or send a quick email.
Much of your vacation will be spent in exploration of Osterville, Cape Cod, and its many adventures and activities, but there may be some days when you just want to laze at your rental. Many Osterville vacation rentals provided by Pretty Picky Properties have plenty of things to do, right inside the home. In select homes you’ll enjoy books, board games, toys, and more in select homes that will keep everyone busy on those days when you take a break from going out.
Candace Cooper
My family rented from them two years ago and it was an easy and responsive experience. Looking to book with them again in 2021.
Bj Durante
Wonderful people honest ,trustworthy,motivated,capable and enthusiastic very hard to find people like this today .Were very lucky to have them.
Evan Pasenello
Great rental experience! Awesome commutation and very responsive service.
Our Osterville vacation rentals boast the privacy you get in your own home, no matter how you choose to experience a Cape Cod vacation. When you want privacy, privacy is what you’ll get. With separate living and sleeping areas, as well as the quiet neighborhood of a private home, everyone can enjoy vacation in their own way.
The private bedrooms in our Osterville vacation rental homes feature stylish furnishings, comfortable mattresses, cozy sheets, and blankets that provide a good night’s sleep or refreshing nap between fun Osterville and Cape Cod activities. Select properties offer even more privacy, with en suite bathrooms. Take your time with your morning and evening routines without someone banging on the door, impatiently waiting for “their turn” in the bathroom. Relax the day away in spacious showers or separate soaking tubs, so you begin and end the day with complete relaxation.
No matter how long you’re in Osterville with us, take the time to unpack and settle in at your vacation rental provided by Pretty Picky Properties. Large closets and spacious dressers in each bedroom hold all of your things and make relaxing on vacation and letting go of stress easy.
While you’ll be getting out and seeing the many sights of Osterville and the surrounding area, make sure to spend some time enjoying outdoor amenities of your Osterville vacation rental provided by Pretty Picky Properties, too.
Spending time outdoors can start right at your property! Each of our Osterville vacation rentals boasts amenities like sprawling decks, patios, or balconies where you can breathe in the salty sea air of Nantucket Sound. Watch the waves or blend them into the background noise of an al fresco meal or glass of wine.
Lounge on outdoor furnishings, or just step out and take in the view. On beach days, pack up your gear and head to the beach. Select homes have private walkways that lead you right onto the sand and only steps from the ocean! If you’re looking for a dip that’s doesn’t include sand and salt, select Osterville vacation rental homes have a private pool or spa. You’ll get a refreshing or relaxing dip with only a few steps outside your door. Relax after a day of adventuring and sink into the spa. If getting wet isn’t on the agenda at all, take a seat in the sun and soak up the rays instead. Whatever your outdoor plans may be, there’s a place to relax and enjoy your Osterville vacation.
When you stay in one of our Osterville Cape Cod rentals provided by Pretty Picky Properties, you’ll enjoy easy access to the beach and the crashing waves of the breathtaking Nantucket Sound along Cape Cod. You’re just moments from area attractions, shopping, dining, and more, too.
We’re here to help you create a Cape Cod and Osterville adventure that’s unique to you and your loved ones. We have a home in Osterville to suit your needs, with properties as large as four bedrooms! Plan a family or group reunion near the beach, or a simple getaway with your sweetheart. Whatever your vacation plans are, we are here to help!
Contact us to start planning today!
Your Osterville vacation home is prepped and ready! We provide a variety of starter essentials to help you settle in comfortably. If you run out, local shops are just a short drive away. Guests staying in one of our Luxury Collection homes will also enjoy upscale bath products like shampoo, conditioner, and body wash.
Osterville is a charming village with a compact, navigable layout. While you’ll find some shops and eateries within walking or biking distance, having a vehicle is the best way to explore the surrounding Cape Cod area and hidden coastal gems.
Summer in Osterville is filled with coastal charm. You can enjoy beautiful beaches, explore the scenic walking trails at Skunknett River Wildlife Sanctuary, shop in the quaint village center, or grab fresh seafood at one of the harbor-side restaurants. The town truly comes alive with sunny days and community events.
