Holiday rentals in Dennis Port

4.82 out of 5 average rating, 483 reviews

Tiny home in Dennis Port

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

4.95 out of 5 average rating, 212 reviews

The Strandloper / Beachwalker Cottage

This very clean and spacious 1 bedroom cottage has AC, is within walking distance to two public Nantucket Sound Beaches and is centrally located on Cape Cod. The vaulted ceilings and ample array of windows gives off natural light and a sense of space. FYI The cottage's name, The Strandloper, the Beachwalker, is a member of an extinct tribe of Khoikhoi Bushmen who lived on seafood gathered along the beaches of Southern Africa. Walking beaches is just as special today as it was a millennium ago.

4.97 out of 5 average rating, 178 reviews

4 Minute Walk to Beach, Cape Cod Serenity

Located on a quiet corner with lots of privacy, 2 full baths, 4 bedrooms, outdoor shower, and a quick stroll to the beach. Activities, great restaurants and shopping are moments away. Fully equipped kitchen, linens included, outdoor seating, a grill and beach accessories will make your trip great. 1 full bath down with two bedrooms, 1 full bath up with two bedrooms. AC/Heating units installed to make your stay more enjoyable! June, July and Aug are 7 day stays w/ Friday as arrival day!

4.93 out of 5 average rating, 111 reviews

Home in West Dennis

Adorable Cottage - Premier Location in West Dennis

**5 Blocks to West Dennis Beach** This adorable house is in the most desirable West Dennis Beach Neighborhood only a short 7-minute walk to the public beach. With two spacious bedrooms, an eat-in kitchen and a bonus room/sunroom/optional 3rd bedroom, there is plenty of room to spread out. Across the street (300 ft) is Kelley's Pond which is great for kayaking, canoeing and fishing! Come sit by the fire pit or on the deck, cookout and relax!! Firewood is included but bring some kindling!

4.93 out of 5 average rating, 257 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

Superhost

4.83 out of 5 average rating, 42 reviews

Oceanfront 3 bedroom cottage with private beach

Unwind at this stunning 3 bedroom Dennis Port oceanfront cottage. Enjoy sweeping views of the ocean from the comfortable living room or the spacious outdoor patio. Walk down the beach stairs to your own private beach. Equipped with two parking spots, wifi, and a smart TV, this peaceful cottage is perfect for couples, families, and friends. Steps away from the Pelham House Resort and a short walk to the Ocean House Restaurant, Sundae School, Woolfie’s Bakery and many other Dennis Port gems.

4.97 out of 5 average rating, 104 reviews

Flat in Dennis Port

Apartment suite|pond access|Firepit|Private Deck

Enjoy a stylish experience at this centrally-located spot. Our newly built apartment suite is within walking distance of Dennis Port for restaurants, yoga, and an organic market. Private parking, entrance, and deck along w/ water access to Swan Pond. A full kitchen & Bath equipped with a new LG washer + dryer makes this space feel like your home away from home. Explore, play, rest & relax. We have all you need for a wonderful retreat to make your trip to the Cape an enjoyable one.

4.96 out of 5 average rating, 28 reviews

Bo's Place

Enjoy your own cozy, rustic cottage nestled within a welcoming, tiny cottage community. Take a 5 minutes walk to a private beach to enjoy the sun and waves without the crowds. Afterwards, rinse the sand off in the outdoor shower, underneath the trees. You can either choose to make a meal indoors or crack into some fresh lobsters while sitting at the outdoor picnic table under the string lights. Then retire on the comfy couch or have a glass of wine outside by the fire.

5 out of 5 average rating, 28 reviews

Tiny home in Dennis Port

Pearl Haven: A Seaside Cottage

Located directly across from the beach, we welcome you to Pearl Haven, our “tiny” coastal escape on the coast of Dennis Port, MA! Nestled within a seaside cottage community, Pearl Haven is just steps away from the shimmering shores of Nantucket Sound. Our cozy studio cottage is a newly renovated, charming retreat designed for simplicity and comfort. *Note: 7 night stay, Sat-Sat for June 21- July and August. (2025 exceptions: August 16-19, 22, 30, 31)

4.95 out of 5 average rating, 185 reviews

Apartment in Dennis Port

#5 Nautical Nest Studio 300 yards to Glendon Beach

Newly renovated, 250 square ft studio at Near Beach Rentals. 300 yards to Glendon Beach. Fully furnished studio awaits for your Cape getaway. Head to the beach in the morning and you're close enough to walk back for lunch. The studio comes with a queen bed, a twin bed, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture.

4.99 out of 5 average rating, 116 reviews

Cottage in West Dennis

5 min walk to beach w/ Fire Pit & Modern Amenities

Just 5 minutes from the beach, this updated Cape Cod home is perfect for small families seeking a relaxing getaway. Inside, enjoy a remodeled space with modern comforts and cozy charm. Out back, unwind on the patio with a lush lawn and easy-start gas fire pit—great for dinners or s’mores under the stars. Stocked with linens, beach gear, toys, games, Wi-Fi, AC, full kitchen, and grill. Close to Holiday Hill mini golf, ice cream, and seafood shacks!

4.96 out of 5 average rating, 143 reviews

Escape to the Cape

Come stay at my comfy Cape cottage! My 2 bedroom 1 bath cottage comfortably sleeps 5 and is perfect for any family getaway. It's centrally located on Cape, less than a mile from the beach, features central air conditioning, heat, wireless internet, smart TV, an outdoor shower with changing room. Gas grill and patio table, too! JULY 5, 2025 - AUGUST 22, 2025 ARE SATURDAY TO SATURDAY WEEKLY RENTALS WITH CHECK-IN ONLY ON SATURDAYS.

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Popular amenities for Dennis Port holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Dennis Port

5 out of 5 average rating, 20 reviews

Home in West Harwich

Romantic little Cape Cod Cottage on Rail Trail

HanaburghRating, 5 stars2 days ago

Our stay at this charming, one-bedroom cottage was everything we hoped for and more. From the moment we arrived, we were enchanted by its storybook charm—complete with a white picket fence and blooming flowers. Inside, the exposed beams and cozy décor gave it the perfect blend of rustic and coastal charm. We started every morning on the back deck, sipping coffee and listening to the birds—it truly felt like a hidden sanctuary. The house itself was spotlessly clean, well-maintained, and thoughtfully stocked. The water pressure in the shower was amazing (not always easy to find but greatly appreciated), and every detail felt considered. There was nothing we needed that we couldn’t find within its white cabinets. It was quaint and quiet, but still conveniently located to beaches, shops, and restaurants. A perfect blend of nature, comfort, and Cape Cod magic. We'd come back in a heartbeat and hopefully have slightly better weather!!

5 out of 5 average rating, 21 reviews

3-min walk to BEACH! Private luxury Backyard!

CaseyRating, 5 stars10 months ago

This was a great place to stay. The house was just the right size for our family of 4 (two young kids). The fenced in yard with shade structure and yard games were great. We spent a lot of time playing outside. We initially got the place because of the proximity to the beach, and it is a nice short walk to the beach, but ultimately this beach wasn’t quite the right fit for our kids (ages 3 and 1) so we ended up going to a beach on the north side of the Cape instead, which was a better fit. We were really grateful for the chairs and beach toys, which we used when we went to the beach. The beach umbrella wasn’t in great shape, and with a little breeze it wasn’t usable. Also there were a couple shelves in the house that were either broken (medicine cabinet in bathroom) or missing a pin and so unusable (in the kitchen) but these were minor issues and didn’t affect the quality of our stay. All in all, we had a good time!

4.93 out of 5 average rating, 15 reviews

Cozy Summer Cottage w/ Water Access

PhilRating, 5 stars9 months ago

My wife and I stayed at May's place while visiting family on Cape Cod. As described, it's a cozy little cottage, which was just what we wanted. Quiet neighborhood. Most of our time was spent on the delightful patio. A short night-time walk to the pond was exceptional with moon light reflecting off the water. Next time we're on the Cape, we definitely return.

4.94 out of 5 average rating, 16 reviews

Meander Beach Cottage with Private Backyard

ClarkeRating, 5 stars8 months ago

Carrie’s home was amazing! Very close to the beach and we were able to walk to the Ocean House for dinner which was incredible. The beds were extremely comfortable and everything was as pictured. We would love to visit again.

4.98 out of 5 average rating, 59 reviews

2 Minute Walk to Beach, Cape Cod Escape

ValerieRating, 5 stars2 weeks ago

This is our second time staying here. The location is excellent and the cottage comfortable. Planning our next visit.

4.88 out of 5 average rating, 17 reviews

Beach Bungalow: Steps to Beach, Luxury Family Fun

IanRating, 5 stars1 month ago

We loved the home! It was very cozy and in a great location. Everything was as described and the hosts went above and beyond to communicate information on the area as soon as we booked it. Thank you so much!

5 out of 5 average rating, 6 reviews

Home in South Yarmouth

Sauna I Walk2Beach I Pet Friendly I Fire Pit

MollyRating, 5 stars6 days ago

We loved our stay here! Spent the weekend with our two young children and the house had everything we could need and more. It was walking distance to the beach and near great restaurants. Victoria also provided a list of local recommendations which we took a few of and loved them all! Would recommend staying here.