
Guesthouse vacation rentals in Dennis
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Top-rated guesthouse rentals in Dennis
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Popular amenities for Dennis guesthouse rentals
Family-friendly guest house rentals

West Chop Cottage + Beach Access
We had a great stay with Peggy! She is wonderfully kind and we had everything we needed to relax and adventure on the island. Such an amazing location and cute, cozy space, would highly recommend!

Peaceful, Family-Friendly Cottage, w/Private Beach
Johanna's historic cottage was magical. It's in a very special spot. Staying there felt like a step back in time with the 16" wide plank floors, orginal doors and colonial latch hardware, the enormous brick fireplace, that must have been the kitchen hearth and the low beamed ceilings. It is superbly located steps from Wellfleet Harbor and the oyster flats where there's a gorgeous peaceful beach. The seafaring culture, history and early american architecure are completely enveloping and enchanting. Excusions to anywhere on the Cape were just a hop skip and jump from Wellfleet, which really enriched my whole stay there. I have no hestitation in recommending Johanna's cottage.

Joe's Beach Hideaway
Joe’s place was perfect for our short little getaway! We had our dog, so much of what we did was go for walks, check out the beaches, explore the area, and get takeout. Joe was sure to provide us with many local recommendations. He was flexible with our check-in and provided clear instructions. He was also very responsive throughout our stay. The unit was very cozy and well appointed. I can only imagine how enjoyable it is in the warmer months! We hope to come back someday! Thanks again ☀️

Mermaid Cottage
What a perfect, cozy space to spend our long weekend on Martha’s Vineyard! This place is better than the pictures. Beautifully decorated, well stocked, comfortable bed, so quaint, and peaceful location. This is an easy drive to all towns on the island. It comfortably fit two adults and our infant. We would hands down return!

Osterville Guest House
Truly enjoyed the space. It was right next to a lot of cute local shops. Would recommend!

Cozy 2 bedroom home near Rock Harbor/ bike trail
the place was comfortable, spacious, very clean. The kitchen was well stocked. very good shower. Of note, if you are a very light sleeper like me, there is an apartment upstairs. The person living above us was extremely quiet but I was woken up by the sound of the toilet flushing upstairs on some early mornings. Only because I am a very light sleeper. The refrigerator is also quite loud (older model) and since this is an open space design, some of my family members noticed and found it annoying. All in all we enjoyed our stay and would rent this place again!

Marthas Vineyard 1BR Cottage 10 min to beach/town
Exactly as pictured! Had a wonderful week and can’t say enough about the magical outdoor shower. Enjoyed having my dog with me and convenience of walk to beach location. We walked into Edgartown every morning- using bike path. Lovely way to start the day. Would absolutely book again (and again)

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER
Kati and her husband Mark were fantastic hosts! They were extremely friendly and helpful. The ‘Big Chill’ was just as nice in person as it was in pictures. It was clean and spacious and nice to have a downstairs area to hang out in and plenty of sleeping space upstairs. We could easily walk to the market for pastries, coffee and groceries and was an easy 5 minute drive to Edgartown . The surroundings were beautiful and we even saw deer and wild turkeys on the property! We would definitely stay there again!
Guest house rentals with a patio

Harwich Port - "Lee Side" cottage by the beach!
It is rare that an Airbnb will significantly exceed expectations, relative to its price/value, but in the case of Dan’s cottage, you will find exactly that. The space itself is the perfect home base for operations around Harwich - sleeping arrangements, seating areas, kitchen/bathroom all were fantastic for two couples. Dan and his son Tim are world class hosts, and went above and beyond to accommodate our group. It is a literal stones throw to excellent local pubs/groceries, and not more than a 5 minute stroll to the beach. There is no where else I would rather stay in the Cape than Dan’s cottage. Thank you very much for the hospitality and I look forward to returning again.

Private cabin in Wildlife Habitat; near bus route
As long as you don't mind having only an outdoor shower,which I didn't since the weather was beautiful, Judys place is a nice quiet cozy nook surrounded by lovely well kept grounds. Total privacy. Judy was a very attentive host, allways checking in via emailand offering to go beyond what I expected.

Private Two bedroom Katama cottage near Edgartown
Great stay! Location was very good, central to everything but very private at the same time. Very nice host and really appreciated the goodies from Morning Glory Farm. Thank you!!

Private 1 king bedroom guest house-2021 built
Most comfortable bed ever! The setting was beautiful, lush, green and relaxing. A perfect rejuvenation point for a busy Cape Cod sightseeing stay. The accommodations were well appointed. A great night sleep on a comfortable bed was a bonus!

Cozy, renovated home in a charming duplex cottage
Easy and responsive. The house was clean and well equipped.

Charming W. Tisbury Studio Guest Cottage
This cottage was perfect me, my wife, and our dog! We like the quieter side of Martha’s Vineyard and we found it here. You feel like you’re tucked away, but it’s easy to get to, and you are still within walking distance to a wonderful restaurant, and a short drive to anything else you need. You can get to the most beautiful beaches in just a few minutes. I am so appreciative that Adam was an extremely helpful host and very easy to communicate with. Would love to stay here again!

Carriage House - Oyster Pond, Steps to Beach+Town
Great location, loved our stay!

the Elevated Escape
Allison is a dream host. We stayed at the cottage for our engagement and proposal trip and couldn’t have picked a more perfect place for it. Allison created a magical Cape Cod experience full of beautiful details including fresh flowers, relaxing hammock, chill breakfast deck, whimsical treehouse, soft bedding and wonderful kitchen with views of nature. Everything is designed with fine taste and genuine care. Line of sights flow elegantly and framed beautiful views throughout the space. She left us handwritten notes and generously prepared the space for our engagement photoshoot. We had such a peaceful and romantic time at the cottage that it felt like a sweet home away from home. We left with lots of happy memories and inspirations. Thank you Allison. We truly loved the space and would come back again in a heartbeat!
Guest house rentals with a washer and dryer

Cape Cod Cottage: Walk to the Beach in Brewster!
My daughter and I enjoyed our stay at Jean's charming cottage. Brewster was a great home base for a weekend on the Cape, we particularly enjoyed being able to walk to the beach. We found the cottage spotless and just as lovely as it appears online. The beds were very comfortable, and we both enjoyed the skylights while falling asleep and waking up. Jean was enthusiastic and quick to respond when we had a few questions. I do suggest you take note of the layout of beds/seating upstairs to be sure it works for your needs. We highly recommend Jean's cottage and would be very happy to stay there again in the future!

Guest house over Garage
Joe’s place was wonderful private and very well appointed. Highly recommended for a getaway in a lovely neighborhood. You can also put on a light backpack and hike down to the beach, which is a short hike. Please tell them that Greg sent you.

La Casita
Lovely home, well-maintained and quiet. A beautiful place to rest as well as easy access to bike trails and towns. We used the outside shower the whole time and it was so refreshing. Had an incredible dinner at Lambert’s Cove in the garden.

Quiet, Pet Friendly, Close to Edgartown and Oak Bl
We had a great stay in the off season. The house was comfortable and clean.

Cape Cod beach inspired “Makondo” Suit Apartment!
We had a great stay at Cristian and Yuri Paola's place. It was just like the pictures and very quiet and relaxing but near to everything Cape Cod has to offer. Thanks so much for all your help during our stay!!

Gorgeous Apartment close to beaches & bridges
Judith was a great host. She kept in touch with us periodically to see if we had any questions or concerns. Her restaurant recommendations were spot on. We especially appreciated the welcome wine and cheese and terry bath robes. The studio apartment met our needs and was very comfy. The property was full of gardens, statues, and picturesque marshes- a delight for the senses. Would return anytime.

Cozy Vineyard Cottage
This was a very cute cottage! Edward and his wife were very friendly. They let us check in early, the place was very clean. They have chairs and beach accessories, a fully stocked kitchen with pots, pans, utensils, cookware…etc. There is laundry and a cute little work space if you need to work. I would definitely recommend staying here!

Woods Hole Cottage close to Beach and Village
What a perfect little airbnb! This was the second year in a row that my wife and I stayed here with our toddler-aged daughter. I don't have much else to add beyond my review of last year other than everything was the same again in all the best ways. We did learn it's better, and easier, to take the bike path into town, accessing it via a path on the side of the cemetery behind the church. Once again, the owners were super kind and friendly. The place has even been upgraded in the past year with improved furniture and washer and dryer. A+++, would definitely recommend.
Quick stats about guesthouse rentals in Dennis
Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.4K reviews
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Whydah Pirate Museum, Sesuit Harbor Cafe, and Captain Parker's Pub
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- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Cape Cod National Seashore
- Craigville Beach
- Duxbury Beach
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Coast Guard Beach
- Pinehills Golf Club
- Nickerson State Park
- Chapin Memorial Beach
- Grey's Beach
- Scusset Beach
- Corn Hill Beach
- Minot Beach
- Earle Road Beach
- Cahoon Hollow Beach
- Baker's Beach Club
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