Guesthouse holiday rentals in Dennis

Guesthouse in Centerville

5 out of 5 average rating, 132 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

4.89 out of 5 average rating, 174 reviews

Guesthouse in Woods Hole

Quaint Cape Cod Cottage

Quaint cottage on Cape Cod, perfect for a last minute getaway. Amazing location with the beach, Shining Sea Bike Path, The Knob, and Spohr Gardens all within WALKING DISTANCE! A five minute drive to Falmouth Main Street which offers amazing restaurants and shops. In the other direction, another five minute drive will bring you to the historical seaside village of Woods Hole, home to world renowned scientists, numerous beaches, restaurants, museums, an aquarium and the Martha's Vineyard Ferry.

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Guesthouse in Pocasset

4.79 out of 5 average rating, 162 reviews

Rustic Carriage House by the Sea

This authentic small old Cape Cod rustic carriage house is charming, antique, and unique. It is situated in a beautiful,-of-a-kind location, loaded with cozy fun, making a great getaway time of the year. The carriage house is within distance of beautiful Hens Cove and is near many activities such as bike paths the cape cod canal, ferries, hiking fishing, and numerous restaurants. It is ideal for pet-friendly families, a couple of couples, friends who want to stay together, and larger groups.

4.89 out of 5 average rating, 103 reviews

Guesthouse in Tisbury

Martha's Vineyard Studio Cottage, walk to Lagoon!

This is a studio, guest cottage on a quiet woodland property, 1/4 mile from the main road (Edgartown/Vineyard Haven Road) and VTA bus service. A short walk to the Lagoon (5 min), Vineyard Haven (shopping, ferries), The Manuel F. Correllus State Forest (bike path), The YMCA of MV (day passes avail), The MVRH Performing Arts Center (concerts/performances), 10 minute drive to local beaches (Bend-In-The-Road Beach, Oak Bluffs / Joseph Sylvia State Beach, Edgartown / Beach Road, Vineyard Haven).

4.94 out of 5 average rating, 124 reviews

Guesthouse in Plymouth

Charming Pond-Front Boathouse

Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

4.97 out of 5 average rating, 190 reviews

Guesthouse in Wellfleet

Abundant Blessings Cottage – Wellfleet

Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

4.94 out of 5 average rating, 18 reviews

Guesthouse in Barnstable

Sweet Millie Guesthouse

Kick back and relax in this calm and stylish space where Barnstable, Mashpee, and Sandwich meet. This open concept bedroom/living area with queen sized bed is perfect for your Cape Cod getaway. Conservation and trails right in the neighborhood. Private entrance and private deck to enjoy the fall evenings, full kitchen, washer/dryer. Plenty of parking. Mashpee Commons, Mashpee beaches, Sandwich restaurants, Sandy Neck beach, Hyannis restaurants and beaches all within 10-15 minute drive.

4.96 out of 5 average rating, 211 reviews

One bedroom guest house on beautiful Cape Cod

Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

4.86 out of 5 average rating, 125 reviews

Guesthouse in Barnstable

Relaxing Cottage in Centerville Village

Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with fire pit. Just a short walk to the ocean, beaches, the library and the general store.

4.96 out of 5 average rating, 191 reviews

“The Pink Cottage” in Historic South Yarmouth

“The Pink Cottage” is a charming one-bedroom private building nestled into a beautiful historic property in South Yarmouth. Enter through the pergola patio, enjoy a spacious living space with dining and kitchen area. The one-bedroom with large closet is comfortably outfitted with all linen necessities, full bath with stand-up shower. Outdoor shower just off the patio, grill and more! Very quiet and private.

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What guests are saying

1-Bedroom seasonal cottage near National Seashore

4.95 out of 5 average rating, 21 reviews7 months ago

As first-timers to Wellfleet, we really loved how easy it was to get to the beaches, restaurants, and surrounding areas from Leslie's place, but we also felt like we were away in the woods when we wanted to be. Having stayed in loft-style rentals elsewhere before, this one was much more spacious and navigable than others. It's cozy, but very roomy as well and set up for a couple to move around and be in opposite areas if needed. Regarding amenities, they're not necessarily 21st century furnishings but they fit with the personality of the structure and the surrounding area. Everything worked just fine. The outdoor shower was hot, comfortable, and out of view -- no worries there. If you want to hole up on the Cape in the off-season or have a nice getaway during the summer, this would be a recommended landing spot. Looking forward to returning to this rental at some point, as it's just what we needed.

Guesthouse in Wellfleet

What guests are saying

The Cotuit Bungalow

4.89 out of 5 average rating, 89 reviews8 months ago

This the kind of spot one comes to enjoy the quiet elegance of what Cape Cod offers. Beautiful homes and gardens. Adorable villages rich in history. And if that wasn’t enough…the food was fabulous and the residents were some of the friendliest people I have ever encountered.

Guesthouse in Cotuit

What guests are saying

Wellfleet loft-style guest house close to beaches

4.97 out of 5 average rating, 37 reviews3 months ago

I have stayed at a lot of Airbnbs, and I loved this one. The space was very clean, and the kitchen had everything I needed. There is something special how the space is decorated, it's thoughtful and has positive energy. It's very quiet and peaceful on this road, and the windows in the front look onto a beautiful group of trees. It's very comfortable and close to Wellfleet. Jen accommodated my last-minute request to book this, and responded really quickly whenever I had questions. The house was warm and cozy on a cold, windy weekend in January! I would definitely stay here again.

Guesthouse in Wellfleet

What guests are saying

Oak bluffs cottage Perfect place to honeymoon!

4.98 out of 5 average rating, 90 reviews1 month ago

We loved staying at Oak Bluffs Cottage and would recommend it to anyone visiting Martha's Vineyard! Faith and Lew were so kind and responsive, giving great recommendations for things to do on the island. The place was so cozy, and we really appreciated the snacks, coffee, and beverages that came with the place. The squirrel/acorn theme was super cute too. We give this place 5 stars—the hosts truly went above and beyond to make our style enjoyable!!!

Guesthouse in Oak Bluffs

What guests are saying

Sankaty Light Studio Cottage

5 out of 5 average rating, 11 reviews8 months ago

Kathlene's place was great for our stay on the Cape. The convenience of having a kitchen, the proximity to the beaches and Hyannis Port, for a day trip to Nantucket, and the always helpful host made us feel welcomed and at home. Check in when we arrived was a breeze and Kathlene was very responsive and proactive when we had questions. We will definitely contact Kathlene again when we come back to Cape Cod!

Guesthouse in Yarmouth

What guests are saying

Claw Foot Tub & King Bed at Club Tanuki Cottage

5 out of 5 average rating, 10 reviews6 months ago

One of the best Airbnb’s we have ever stayed in, Bekah was an outstanding host and the home is so cozy and comfortable in a fantastic location on the cape. Perfect for a couple or solo, we were able to access everything on the Cape easily with a rental car. Internet was good, we were able to cook a lot with a well stocked kitchen, and the bathtub is a great feature. Bekah really made it special by going above and beyond as a host and giving great recommendations to make our trip special. This is truly a hidden gem and perfect for a longer stay. Thanks Bekah!

Guesthouse in Brewster

What guests are saying

Secluded home for Cape Cod relaxation, exploration

4.96 out of 5 average rating, 98 reviews5 months ago

We loved our stay here! It was nice, quiet, and clean. Private apartment at the back of their property with a beautiful view of the woods. We only heard noise from somewhere else a handful of times, which was really nice. Well located for day trips out to the beaches, and close enough to the grocery store without being too close to other people. Harriet & Craig were really responsive and proactive communicators! We knew exactly what was expected from us before we even got there!

Guesthouse in Bourne

What guests are saying

Cottage - close to Brooks Park

4.96 out of 5 average rating, 23 reviews7 months ago

We had a great stay at Sarah’s cottage. Small, quaint, and perfect for a holiday weekend. Walkable to restaurants, food mart, liquor store and a park. Safe and cozy! What just what we needed for a vacation and was easy to get to and from. Would highly recommend this spot for anyone who wants to visit the area and stay just an arms length from the hustle and bustle town of Harwich. Beaches a mile or so away were sweet and enjoyable too!

Guesthouse in Harwich

What guests are saying

Marshfront Retreat | EV Charger | Private Deck

5 out of 5 average rating, 25 reviews2 weeks ago

thomas's place is truly amazing. very quiet and well kept garden/outdoor area. the studio itself was simple, with a comfortable queen bed, a full bathroom with plenty of towels and the kitchen also had everything i needed to cook with. i loved my entire stay there and would recommend it to anyone anytime and hopefully i will be able to return. thank you thomas.

Guesthouse in Wellfleet

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Popular amenities for Dennis guesthouses

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Family-Friendly guesthouses

Guesthouse in Vineyard Haven

4.94 out of 5 average rating, 126 reviews

West Chop Cottage + Beach Access

Guesthouse in Wellfleet

5 out of 5 average rating, 18 reviews

Peaceful, Family-Friendly Cottage, w/Private Beach

Guesthouse in Dennis Port

4.85 out of 5 average rating, 265 reviews

Joe's Beach Hideaway

4.99 out of 5 average rating, 90 reviews

Guesthouse in Oak Bluffs

Mermaid Cottage

4.9 out of 5 average rating, 59 reviews

Guesthouse in Barnstable

Osterville Guest House

Guesthouse in Eastham

4.82 out of 5 average rating, 11 reviews

Cozy 2 bedroom home near Rock Harbor/ bike trail

Private room in North Eastham

4.85 out of 5 average rating, 82 reviews

Rugosa Guest House - Room 4

Private room in North Eastham

4.82 out of 5 average rating, 131 reviews

Rugosa Guest House - Room 5

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Guesthouses with a patio

Guesthouse in Harwich Port

4.95 out of 5 average rating, 20 reviews

Harwich Port - "Lee Side" cottage by the beach!

4.93 out of 5 average rating, 15 reviews

Guesthouse in Edgartown

Private cabin in Wildlife Habitat; near bus route

4.97 out of 5 average rating, 63 reviews

Guesthouse in Sandwich

Private 1 king bedroom guest house-2021 built

5 out of 5 average rating, 65 reviews

Guesthouse in Pocasset

Waterfront Cottage / Your Cape Escape

Guesthouse in West Yarmouth

5 out of 5 average rating, 39 reviews

Cozy, renovated home in a charming duplex cottage

4.96 out of 5 average rating, 23 reviews

Guesthouse in Chatham

Carriage House - Oyster Pond, Steps to Beach+Town

5 out of 5 average rating, 15 reviews

Guesthouse in Forestdale

the Elevated Escape

5 out of 5 average rating, 24 reviews

Cozy Cottage

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Guest house rentals with a washing machine and dryer

4.94 out of 5 average rating, 82 reviews

Guesthouse in Brewster

Cape Cod Cottage: Walk to the Beach in Brewster!

4.87 out of 5 average rating, 15 reviews

Carriage house in historic district,walk to beach!

Guesthouse in Centerville

4.86 out of 5 average rating, 86 reviews

Guest Cottage

Guesthouse in West Tisbury

4.94 out of 5 average rating, 18 reviews

Guest house over Garage

5 out of 5 average rating, 7 reviews

Guesthouse in Tisbury

Escape to Bungalow 24 on MV!

4.99 out of 5 average rating, 78 reviews

Guesthouse in Brewster

Brand new, on a swimmable pond

4.89 out of 5 average rating, 45 reviews

Guesthouse in Brewster

Cape Cod beach inspired “Makondo” Suit Apartment!