Guesthouse vacation rentals in Dennis

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Popular amenities for Dennis guesthouse rentals

Family-friendly guest house rentals

Guesthouse in Wellfleet

5 out of 5 average rating, 18 reviews

Peaceful, Family-Friendly Cottage, w/Private Beach

BrettRating, 5 stars4 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, 263 reviews

Joe's Beach Hideaway

JuliaRating, 5 stars3 weeks ago
Our stay at Joe’s was absolutely perfect. He has everything you could possibly need and we had an amazing time with no issues. Very clean, walkable to the beach, easy to check in and out! Thank you, Joe!
Guest favorite

Guesthouse in Barnstable

4.9 out of 5 average rating, 59 reviews

Osterville Guest House

MonicaRating, 5 stars3 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 stars17 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!
Guest favorite

Guesthouse in Falmouth

4.72 out of 5 average rating, 68 reviews

COZY GUESTHOUSE

CarmellaRating, 5 stars6 months ago
Our first bnb experience. Check in was easy. It was private and quiet which is very important to us. It had everything we needed for a 4 night stay and was also a very sweet place. We spent a lot of time on our bicycles so the location was great for access to bike trails and ferry to Vineyard. I had the horrifying experience of leaving a very important item behind and Brittany was very responsive and assisted in facilitating my retrieval of it for which I was very grateful. I would stay there again although a little pricey but for Falmouth in July there is no better deal.

Private room in North Eastham

4.87 out of 5 average rating, 75 reviews

Rugosa Guest House - Room 4

AllisonRating, 5 stars3 weeks ago
We had a lovely night at the rugosa! Great location and just a quick drive into Provincetown for dinner during the off season. The room was super cozy and the inn had everything we needed. We’ll certainly be back next time we visit the cape!

Private room in North Eastham

4.8 out of 5 average rating, 40 reviews

Rugosa Guest House - Room 3

SheilaRating, 5 stars2 months ago
This historic home has all the charm you could ever want and a cozy feel about it. Our room was comfortable and even has a gas fireplace for the cold evening while we stayed. Coffee in the sunny dining room was a bonus.

Private room in North Eastham

4.83 out of 5 average rating, 47 reviews

Rugosa Guest House - Room 2

MatthewRating, 5 stars4 months ago
Joey's place is the quintessential Cape Cod B&B. Comfortable stay and a great host.

Guest house rentals with a patio

Guest favorite

Guesthouse in Pocasset

5 out of 5 average rating, 65 reviews

Waterfront Cottage / Your Cape Escape

LisetteRating, 5 stars3 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!
Guest favorite

Guesthouse in Chatham

4.96 out of 5 average rating, 23 reviews

Carriage House - Oyster Pond, Steps to Beach+Town

RobertRating, 5 stars4 months ago
perfect location and exactly as described
Guest favorite

Guesthouse in Brewster

5 out of 5 average rating, 10 reviews

Claw Foot Tub & King Bed at Club Tanuki Cottage

BillyRating, 5 stars3 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 East Dennis

4.6 out of 5 average rating, 5 reviews

Charming Cottage in East Dennis

RickRating, 5 stars5 months ago
Great stay ! Awesome host ! Be sure to check out Bandera’s Deli and Southside tavern as well! Thanks ! Would definitely stay again !
Guest favorite

Guesthouse in Forestdale

5 out of 5 average rating, 15 reviews

the Elevated Escape

AnthonyRating, 5 stars4 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!

Guesthouse in Barnstable

4.65 out of 5 average rating, 17 reviews

Beach glamping at the Zen Den

K. ErikRating, 5 stars4 months ago
I have been using Airbnb for 10 years, and I have been so lucky to discover amazing people and places to stay… Murph’s beautiful, private, peaceful, relaxing, and surprising hidden gem was certainly no exception!! And the man is even more impressive than his dwellings. Honestly, from the minute, I started texting with Murph we were like Instafriends, planning mountain bike outings, hang time, having endless positive conversation about health, friendship, family, gratitude, fear, loss, perseverance, and leading the most most fulfilling life possible. I left inspired. And he told me about all the amazing things to do literally out the front door. And he let me borrow his beach bike. And when my plans changed, he not only accommodated me… he gave me a discount?!! Like honestly, who does that??? Anyway, sometimes you show up somewhere and you can’t wait to go back before you’ve even spent the night… and that’s the Zen Den. Looking forward to my next Murph hang & peaceful retreat.
Guest favorite

Guesthouse in Yarmouth

5 out of 5 average rating, 24 reviews

Cozy Cottage

LauraRating, 5 stars3 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 Harwich Port

4.95 out of 5 average rating, 20 reviews

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

LucasRating, 5 stars3 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 Sandwich

4.97 out of 5 average rating, 62 reviews

Private 1 king bedroom guest house-2021 built

SaraRating, 5 stars5 months ago
We loved staying here! The barn was perfect for our first family vacation with our 10 month old. Sandwich is the perfect spot if you are looking to explore cape cod, and we loved being just a short drive to lots of restaurants and the beaches in Sandwich.
Guest favorite

Guesthouse in West Yarmouth

5 out of 5 average rating, 39 reviews

Cozy, renovated home in a charming duplex cottage

BarbaraRating, 5 stars1 month ago
Easy and responsive. The house was clean and well equipped.

Guesthouse in Yarmouth

4.87 out of 5 average rating, 15 reviews

Carriage house in historic district,walk to beach!

KumikoRating, 5 stars5 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 favorite

Guesthouse in Brewster

4.99 out of 5 average rating, 74 reviews

Brand new, on a swimmable pond

WarrenRating, 5 stars3 weeks ago
Our stay at Phillipa's was really nice. We had a wedding which was a ten minute drive away, which was a perfect distance. Her place was really warm and super clean. She left us cookies which I really loved. Definitely a place worth staying in. Thank you so much!!!
Guest favorite

Guesthouse in Brewster

4.89 out of 5 average rating, 45 reviews

Cape Cod beach inspired “Makondo” Suit Apartment!

NadiaRating, 5 stars4 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!!
Guest favorite

Guesthouse in Yarmouth

5 out of 5 average rating, 14 reviews

Pristine Mid Cape Carriage House w/ Ocean Views

AustinRating, 5 stars6 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

    $60 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

    West Dennis Beach, Whydah Pirate Museum, and Sesuit Harbor Cafe

Destinations to explore