Guest house holiday rentals in Dennis

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Popular amenities for guest house rentals in Dennis

Family-friendly guest house rentals

Guest favourite
Guest house 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!
Guest house 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 favourite
Guest house in Dennis Port
4.85 out of 5 average rating, 267 reviews

Joe's Beach Hideaway

SarahRating, 5 stars3 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 favourite
Guest house in Oak Bluffs
4.99 out of 5 average rating, 90 reviews

Mermaid Cottage

AngelaRating, 5 stars2 weeks 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 favourite
Guest house 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!
Guest house 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 favourite
Guest house in Harwich Port
4.95 out of 5 average rating, 21 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 favourite
Guest house in Sandwich
4.97 out of 5 average rating, 63 reviews

Private 1 king bedroom guest house-2021 built

ArtRating, 5 stars8 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 favourite
Guest house 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 favourite
Guest house in West Yarmouth
5 out of 5 average rating, 39 reviews

Cozy, renovated home in a charming duplex cottage

BarbaraRating, 5 stars5 months ago
Easy and responsive. The house was clean and well equipped.
Guest favourite
Guest house 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 favourite
Guest house in Brewster
5 out of 5 average rating, 10 reviews

Claw Foot Tub & King Bed at Club Tanuki Cottage

BillyRating, 5 stars6 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!
Top guest favourite
Guest house 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 favourite
Guest house in Brewster
4.99 out of 5 average rating, 79 reviews

Brand new, on a swimmable pond

SaraRating, 5 stars1 week ago
This was my first time in Brewster and it was a wonderful experience! The apartment was the perfect amount of space to make us feel right at home for our 3 day trip! The decor is beautiful, and it has the most comfortable bed my husband and I have ever slept in!

Guest house rentals with a washing machine and dryer

Guest house 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
Guest house 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
Guest house in Yarmouth
4.67 out of 5 average rating, 3 reviews

Newly furnished-Enjoy sun drenched days

LauraRating, 5 stars8 months ago
The house is definitely old but very charming! Decorated lovely and had everything you could want. The proximity to the Yarmouth beaches was amazing and we loved walking the neighborhoods. Patio was peaceful and perfect for mornings and evenings. Because it’s older, outlets and switches are in funny places, but nothing you can’t make do with. We would absolutely go back!
Guest favourite
Guest house in Brewster
4.89 out of 5 average rating, 45 reviews

Cape Cod beach inspired “Makondo” Suit Apartment!

NadiaRating, 5 stars8 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 favourite
Guest house 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!
Guest house in Sandwich
4.87 out of 5 average rating, 122 reviews

Gorgeous Apartment close to beaches & bridges

JamesRating, 5 stars7 months ago
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.
Top guest favourite
Guest house in Marion
5 out of 5 average rating, 7 reviews

Newly renovated studio in heart of Marion village

AdeleRating, 5 stars2 months ago
Shelly's place was so charming & comfortable, we especially appreciated all of the natural light coming into the home. Shelly is a wonderful host! Definitely hope for another stay in the not-so-distant future.

Quick stats about guest house rentals in Dennis

  • Total rentals

    20 properties

  • Nightly prices starting at

    £30 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

Destinations to explore