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Guesthouse vacation rentals in Dennis

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Popular amenities for Dennis guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Vineyard Haven
4.94 out of 5 average rating, 126 reviews

West Chop Cottage + Beach Access

MichelleRating, 5 stars7 months ago
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!
Guesthouse in Wellfleet
5 out of 5 average rating, 18 reviews

Peaceful, Family-Friendly Cottage, w/Private Beach

BrettRating, 5 stars7 months ago
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.
Guest favorite
Guesthouse in Dennis Port
4.85 out of 5 average rating, 266 reviews

Joe's Beach Hideaway

SarahRating, 5 stars2 weeks ago
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 ☀️
Top guest favorite
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 90 reviews

Mermaid Cottage

AngelaRating, 5 stars1 week ago
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!
Guest favorite
Guesthouse in Barnstable
4.9 out of 5 average rating, 59 reviews

Osterville Guest House

MonicaRating, 5 stars6 months ago
Truly enjoyed the space. It was right next to a lot of cute local shops. Would recommend!
Guesthouse in Eastham
4.82 out of 5 average rating, 11 reviews

Cozy 2 bedroom home near Rock Harbor/ bike trail

LyzaRating, 5 stars20 months ago
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!
Private room in North Eastham
4.85 out of 5 average rating, 82 reviews

Rugosa Guest House - Room 4

VictoriaRating, 5 stars1 month ago
I couldn’t recommend the Rugosa more! Joey was a great host - he was attentive, accommodating and so kind. The common spaces are well decorated, homey and have everything you’d need. The room was perfect - cozy and welcoming and ours even had a jacuzzi tub! We’ll definitely be returning again, hopefully for longer next time!
Private room in North Eastham
4.82 out of 5 average rating, 131 reviews

Rugosa Guest House - Room 5

StephanieRating, 5 stars3 months ago
Joey is the ideal host. Genuine, friendly, and just a nice guy. We’ve stayed at Rugosa 4 times and will keep coming back. Joey is always responsive and so hospitable. It feels like staying at a really good friend’s place, just totally cozy and relaxing.

Guest house rentals with a patio

Guest favorite
Guesthouse in Harwich Port
4.95 out of 5 average rating, 20 reviews

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

LucasRating, 5 stars6 months ago
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.
Guest favorite
Guesthouse in Edgartown
4.93 out of 5 average rating, 15 reviews

Private cabin in Wildlife Habitat; near bus route

ArthurRating, 5 stars7 months ago
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.
Guest favorite
Guesthouse in Sandwich
4.97 out of 5 average rating, 63 reviews

Private 1 king bedroom guest house-2021 built

ArtRating, 5 stars7 months ago
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!
Top guest favorite
Guesthouse in Pocasset
5 out of 5 average rating, 65 reviews

Waterfront Cottage / Your Cape Escape

LisetteRating, 5 stars6 months ago
We really loved our stay! The place was adorable and we felt like the host went above and beyond what I’ve ever seen an Airbnb host do before. They had set aside a little snack basket and some gifts as well as personalized touches. Very clear instructions and lots of special extras (like a cabinet of frequently forgotten items plus first and even shower steamers). It very much felt like the hosts really cared and wanted us to have a wonderful stay!
Top guest favorite
Guesthouse in West Yarmouth
5 out of 5 average rating, 39 reviews

Cozy, renovated home in a charming duplex cottage

BarbaraRating, 5 stars4 months ago
Easy and responsive. The house was clean and well equipped.
Guest favorite
Guesthouse in Chatham
4.96 out of 5 average rating, 24 reviews

Carriage House - Oyster Pond, Steps to Beach+Town

Kevin D.Rating, 5 stars7 months ago
Great location, loved our stay!
Top guest favorite
Guesthouse in Forestdale
5 out of 5 average rating, 15 reviews

the Elevated Escape

AnthonyRating, 5 stars7 months ago
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!
Top guest favorite
Guesthouse in Yarmouth
5 out of 5 average rating, 24 reviews

Cozy Cottage

LauraRating, 5 stars6 months ago
We thoroughly enjoyed our stay! The cabin was very clean and in a quiet neighborhood within walking distance to a sandy beach and excellent seafood restaurant.

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Brewster
4.94 out of 5 average rating, 82 reviews

Cape Cod Cottage: Walk to the Beach in Brewster!

AudreyRating, 5 stars1 month ago
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!
Guesthouse in Yarmouth
4.87 out of 5 average rating, 15 reviews

Carriage house in historic district,walk to beach!

KumikoRating, 5 stars8 months ago
Christin was a gracious host and very responsive to our needs. The only thing I would have any complaints about is that it was a very hot week when we stayed and since there was only one AC upstairs where the two bedrooms are it was quite hot in the bedroom that didn’t have the AC. Other than that, the place was very charming and we very much enjoyed our stay
Guesthouse in Centerville
4.86 out of 5 average rating, 86 reviews

Guest Cottage

KimberlyRating, 5 stars8 months ago
The place was spotless Tina thought of everything little extras that really helped make our stay more enjoyable. She stated the art appliances. Everything was upgraded. She was easily accessible if we had any questions I would highly recommend her place.😊 Kimberly salatino Queensbury, New York
Guesthouse in West Tisbury
4.94 out of 5 average rating, 18 reviews

Guest house over Garage

Michelle And GregRating, 5 stars6 months ago
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.
Top guest favorite
Guesthouse in Tisbury
5 out of 5 average rating, 7 reviews

Escape to Bungalow 24 on MV!

AmyRating, 5 stars7 months ago
Steve was a great host. He immediately responded to get us out of a jam in short notice. He was very communicative. Place was new & updated. Modern beach feel. Great layout & convenient location (we normally stay in Chilmark & this was much closer to everything). It was perfect for us to unwind after some stressful weeks.
Top guest favorite
Guesthouse in Brewster
4.99 out of 5 average rating, 78 reviews

Brand new, on a swimmable pond

MashfiqRating, 5 stars2 weeks ago
This was one of the best Airbnb's I have ever stayed at. Everything was exactly as described in the listing. The place was immaculate and super clean. I felt like I was in an expensive hotel, Phillipa's place is absolutely incredible. There are enough extra linens and so many extra towels. The giant TV with guest Netflix access is so nice. The area is serene. The lake being nearby is fantastic. Good driving distance to multiple Cape Cod locations. It truly felt like a home away from home. I would definitely want to stay here again in the future!
Guest favorite
Guesthouse in Brewster
4.89 out of 5 average rating, 45 reviews

Cape Cod beach inspired “Makondo” Suit Apartment!

NadiaRating, 5 stars7 months ago
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!!
Top guest favorite
Guesthouse in Yarmouth
5 out of 5 average rating, 14 reviews

Pristine Mid Cape Carriage House w/ Ocean Views

AustinRating, 5 stars9 months ago
Mary Lou and Bill were exceptional hosts and their property was absolutely stunning. We stayed in their carriage house with our 3 children and it was a perfect fit. Our kids loved the shuffleboard table and there was plenty of space for them to lounge after a day at the beach or exploring the Cape. They were super generous allowing us to use their coolers, towels, beach chairs, etc. If we had any questions Mary Lou was always very quick to respond and make us feel at home. I’m not sure the pictures do this property justice; again just absolutely stunning and the perfect place for our summer vacation in 2024. Would love to come back and couldn’t recommend it any higher!

Quick stats about guesthouse rentals in Dennis

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 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

    Sesuit Harbor Cafe, Whydah Pirate Museum, and Captain Parker's Pub

Destinations to explore