As you begin to explore all the towns and villages that comprise Cape Cod, you may find yourself drawn to the town of Dennis, offering the feel of a seaside resort and a history that dates back to 1639 when it was first settled. Also home to many of our beautiful and welcoming Cape Cod escapes at Pretty Picky Properties, visitors who decide that Dennis is where their journey is going to bring them can also experience the comforts, luxuries, and special amenities our Dennis retreats will offer. This ultimate Cape Cod guide to Dennis will give you an in-depth look at the places you can visit, the restaurants you will enjoy, and the comfortable adventures you will discover when you come home to our Cape Cod retreats every night of your stay.
Browse our Dennis Vacation Rentals Here!
The Villages of Dennis
There are several villages that make up the town of Dennis, each offering its own personality, attractions, and restaurants, and our Pretty Picky Properties are located in or near every village, so no matter where you are exploring, you will never be far from home. Because each of the villages offer something different, we are going to examine each one, giving you tips on the best attractions, restaurants, and in some cases, the fun events that make visitors feel as if they are one of the locals when they attend.
Dennis the Village, AKA North Dennis
Although Dennis was once a part of Yarmouth, it has developed quite a reputation of being a popular spot for tourists to visit, offering a little bit of everything that reflects the lifestyle of Cape Cod, with the activities listed below being the most notable.
Cape Playhouse, 820 Main Street
If all the world’s a stage, Dennis has long been the setting for summer theater, earning a place in history as America’s longest running summer theater. Also known as “the place where Broadway goes to summer,” some of the world’s most famous stage actors have played their part in the performances that have taken place every summer since 1927. Julie Andrews, Henry Ford, and Betty White have all taken a bow on the famous stage of the playhouse, and your summer getaway to Dennis wouldn’t be the same without viewing at least one show.
Mayflower Beach
Considered one of the most beautiful beaches on Cape Cod, its calm waters, brilliant white sand, and family friendly vibe also makes Mayflower Beach one of the Cape’s most popular. Swimming, skimboarding, and beach volleyball are some of the most popular activities here, as well as sunbathing and relaxing, but families with children who are always curious about life and its variety of creatures will appreciate the stories that the tide pools tell.
Sesuit Harbor Café, 357 Sesuit Neck Road & Fin, 800 Main Street
Located on opposite ends of the dining spectrum, Sesuit Harbor Café & Fin offer unique and authentic Cape Cod dining experiences. Sesuit Harbor Café offers a celebration of the classic Cape Cod restaurant, serving up “chowdah,” lobster rolls, and platters of freshly harvested seafood that will ensure you don’t leave hungry. It does not have a liquor license, but you are invited to BYOB, so no sacrifices will need to be made. Fin, however, is a fine dining establishment, located inside an antique captain’s home, offering a glimpse into history as well as an elevated seafood menu that is also locally harvested.
Dennis Port
Once known for its shipbuilding prowess, Dennis Port is also an artist’s colony, an architectural wonder, and one of the first places in the nation to manufacture salt, adding to its mystique and charm.
Browse our Mid Cape Vacation Rentals Here!
Hydrangea House Gift Shop, 227 Depot Street
For as long as there have been flowers on Cape Cod, hydrangeas have grown here, making them an iconic part of the Cape Cod experience, and the Hydrangea House Gift Shop capitalizes on their colorful beauty. Framed by gardens of, you guessed it, colorful hydrangeas, the building in which all manner of hydrangea themed gifts and art is sold is an 1861 Greek Revival Home that is worth a visit even if it didn’t have any gifts inside! Also purchased as part of a larger plan to create an artist’s colony, this female owned business is a wonderful addition to the shopping landscape of Dennis Port.
Sea Street Beach in Dennis Port
There are actually two Sea Street Beaches in the area. One is in East Dennis, located on the bay side; the one we are talking about now is actually in Dennis Port, overlooking Nantucket Sound. Offering lifeguards during the high season and a large parking lot, this is not the beach for people with mobility problems because the only way to reach its powdery sands is by climbing one of two tall staircases.
The Ocean House Restaurant, 425 Old Wharf Road
Whether you are celebrating a milestone birthday or anniversary or are just celebrating the best vacation you have ever taken, a dinner at the Ocean House Restaurant will make your celebration shine bright. This special occasion restaurant is open seasonally, offering a beach bar that overlooks Nantucket Sound and a fantastic menu filled with surf, turf, and Asian specialties and will become an integral part of your celebration.
East Dennis
Quiet and relaxing, East Dennis is the ideal place to visit when you don’t want to deal with the crowds of tourists that can be found in many other Cape Cod towns and villages. A smaller village, you may end up spending more of your time exploring the amenities of our Pretty Picky Properties Dennis retreats, but you may also find yourself enjoying a day on Sea Street Beach, (Remember, there are two Sea Street Beaches!) savoring the serenity that permeates every sea activity or enjoying a fabulous meal at Grumpy’s, located at 1408 Main Street. Open daily for breakfast and lunch, some might go as far as to say if you don’t experience a breakfast at Grumpy’s at least once during your getaway, you will be questioned on the authenticity of your entire Cape Cod vacation experience! Every meal is wonderful at Grumpy’s, but you might want to turn your attention to their Eggs Benedict menu, offering nine different variations that all deserve to be devoured; we love their seafood cake benedict, and their eggplant spinach roasted peppers benny is sure to delight your taste buds!
Browse our Saturday to Saturday Rentals Here!
South Dennis
Although Dennis is known for its stunning beaches, South Dennis is the only village that doesn’t offer direct ocean access. Some people may consider that a problem, but because all the villages are so close to each other in Dennis, you won’t have far to roam before finding your own stretch of beach on which you can work on your tan, splash around in the surf, and go beach combing for shells and sea glass. (Have you seen some of the art pieces artists are making from sea glass?)
Devil’s Purse Brewing Company, 120 Great Western Road
In our minds there are many wonderful ways to enjoy a summer’s day on Cape Cod, and Devil’s Purse Brewing Company in South Dennis is definitely one of those ways. Closed on Mondays and Tuesdays and offering a beer patio that will allow you to celebrate the season with beers brewed on the premises, including Handline Kolsch, which was originally brewed in Germany but is so much better brewed on this side of the pond. On most days they will sell snacks from food trucks, but if you are here on a day when food trucks aren’t, you are definitely invited to bring your own snacks. Also offering special events that include Lobster Donut Popups, live music, and dog bowl painting sessions, we can’t forget to tell you that leashed dogs that are well behaved are invited to join in your adventures in beer.
Scargo Tower, Scargo Hill Road
Scargo Tower is a 30-foot-tall stone tower that sits atop Scargo Hill, offering views that will take your breath away and providing a peaceful spot to relax and watch the sun set. Originally a shorter tower built of wood (the original Scargo Tower was only 28 feet tall), this stone structure and its predecessor were always meant to be observation towers, at one point offering a telescope that allowed visitors to explore the area even closer. Scargo Tower as it stands today was renovated in 2019, ensuring that your climbing adventures will be safe ones!
Lost Dog Pub, 1374 MA-134
We have always believed that pizza is the international language of love, and although Cape Cod is known for its seafood, we sincerely hope that our South Dennis guests will sample the pizza offerings found at the Lost Dog Pub. Offering a menu that does include a wonderful selection of seafood that is tasty and locally sourced, we hope that you try their pizza at least once, and if you crave seafood but also want pizza, their surf & turf pizza will never let you down. Created with garlic, olive oil, scallops, bacon, and mozzarella, one bite of this special pie and you will be hooked for life!
Cold Storage Beach, 66 Salt Works Road
Parking for Cold Storage Beach is for residents only, but if you want to enjoy a beach experience without venturing too far from home, ensuring that you will make memories you won’t ever forget. Known for its calm waters and for offering the ideal spot to watch all the boats coming in and out of Sesuit Harbor or at the very least, swim, frolic, and search for seashells and colorful sea glass. Dogs are allowed on Cold Storage Beach during the off season, which can be a fun experience for pups that have never played in the sea.
Check Out our Barnstable Vacation Rentals Here!
A Peek into Comfort
Choosing Pretty Picky Properties for your Dennis vacation accommodations is the easy choice, but you might have a little bit of difficulty narrowing your selection down to just one. Our properties are designed to make your traveling to Cape Cod experiences luxurious ones, comfortable ones, and ones that you will never forget, and as you spend your daylight hours exploring Cape Cod, coming home to our homes will add another element of wonderful to your getaway.
Our Dennis retreats, found in the villages that make up this beautiful town, are family homes offering as many as 5 bedrooms and an equal (or higher) number of baths. The kitchens will be spacious and equipped with updated appliances and room for the kids to sit at the breakfast eating a bowl of cereal. Living rooms will be furnished with what we like to call nappable couches (you know what we mean), and more often than not will feature stone fireplaces (it can still get chilly in the summer months) and state of the art televisions. These properties may be located in the middle of town or on the sandy shores of our Dennis beaches, and every moment you spend inside will be ones that you cherish.
Browse our Cape Cod Luxury Vacation Rentals Here!
Family Experiences and Traveling to Cape Cod
The amenities we offer outside will enhance your family vacation experience, perhaps enticing you to pencil in at least one day to play at home. From the colorful hydrangea gardens that bloom cheerfully in large backyards to crystal-clear swimming pools, bubbling hot tubs, and firepits that will warm up your nights, these outdoor spaces are an oasis of fun. Barbecue grills, dining tables, lounging spaces, and the occasional outdoor game; all of these extras work together to give you the idyllic Cape Cod vacation experience you deserve! Some of our properties may even feature indoor game rooms or maybe just a pool table set up in an open space, offering you more ways to play. Every attention is paid to every detail when you choose Pretty Picky Properties for your Dennis vacation accommodations.
Come Home to Comfort Every Night of Your Stay
Reserve your favorite Cape Cod escape today and start preparing yourself for a vacation that will remind you dreams really can come true!
