Guesthouse vacation rentals in Dukes County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Dukes County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Chilmark
4.94 out of 5 average rating, 90 reviews

Beautifully Renovated 1800s Chilmark Barn

TracyRating, 5 stars6 months ago
Jessica was an amazing host! I’ve been talking with Jessica for about nine months in preparation of coming to stay here for my stepdaughter‘s wedding. She was so helpful so flexible she’s very informative. She loves living here, which makes it so much better to enjoy because she has so much knowledge about the island . The Property was beautiful andamazing! She’s an amazing host extremely hospitable and makes you feel so welcome. We will be coming back!
Guest favorite
The charming cottage exterior features a stone pathway leading to the entrance, surrounded by lush greenery and flowering bushes. A wooden gate provides access to the private yard, with a tranquil lawn area inviting relaxation.
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!
Guest favorite
Guesthouse in Edgartown
4.74 out of 5 average rating, 47 reviews

Marthas Vineyard 1BR Cottage 10 min to beach/town

CarolRating, 5 stars7 months ago
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)
Top guest favorite
A bright living area features a comfortable seating arrangement with soft, neutral-toned couches. Natural light fills the space through multiple windows, and a rustic wooden coffee table enhances the cozy feel. A small dining area is visible in the background.
Guesthouse in Edgartown
5 out of 5 average rating, 21 reviews

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

JenniferRating, 5 stars6 months ago
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

A charming guesthouse is framed by a well-maintained lawn and a large tree, which provides shade. The exterior features white siding with historical accents, and the windows are adorned with decorative elements. Soft lighting emanates from the interior, creating a welcoming ambiance.
Guesthouse in Edgartown
5 out of 5 average rating, 3 reviews

Beautiful Charming Edgartown Guesthouse 1 Bedroom

LizaRating, 5 stars10 months ago
It was a pleasure meeting Ronald and Gayle - they were fantastic hosts - very welcoming, polite, and friendly. We really enjoyed our stay in their adorable little guest house. The cottage is very quiet, clean, comfortable, modern, efficiently designed, and tastefully decorated. It has a lovely view of a manicured lawn and beautiful plantings. We hope to stay here again!
Guesthouse in Edgartown
4.75 out of 5 average rating, 8 reviews

Mushroom Cottage

BillRating, 5 stars8 months ago
Great, cozy Martha’s Vineyard “studio.” Bikeable to Edgartown and Oak Bluffs. Bus stop nearby, but set back from road. I appreciated the powerful A/C during a really hot and humid week.
Guest favorite
A brick patio is depicted, featuring a lounge chair and a small dining area with outdoor seating. A gas grill is visible, providing space for outdoor cooking. Surrounding greenery and trees create a natural, shaded ambiance, enhancing the outdoor experience.
Guesthouse in Edgartown
4.93 out of 5 average rating, 15 reviews

Private cabin in Wildlife Habitat; near bus route

ArthurRating, 5 stars8 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
A stone patio features a round dining table surrounded by chairs, shaded by a vibrant red umbrella. A barbeque grill is visible nearby, with a backdrop of lush greenery and weathered wooden structures, creating a cozy outdoor space.
Guesthouse in Oak Bluffs
4.89 out of 5 average rating, 9 reviews

Cozy Vineyard Cottage

DonaldRating, 5 stars7 months ago
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!
Guest favorite
Guesthouse in Tisbury
4.97 out of 5 average rating, 75 reviews

King bed, Water Views,AC,Near Bike Path- Bus stop

StephanieRating, 5 stars7 months ago
This is our 2nd time staying at MV Sunrise. Stephen is a great host. Love the location. 10 minutes from Circuit Ave in Oak Bluffs. 20 min from Norton Point Beach in Edgartown. Only 5 min from the ferry in Vineyard Haven. King bed, TV upstairs and down and AC on both levels. We always come to MV for the fishing derby in Sept / Oct so we don't use the AC much. Love the cross breezes from all the windows that can be opened. One night it stormed and was too humid for our comfort so we were grateful for the AC that night. Once again, Stephen stocked all the little things. Cut my finger on my spouse's razor, thank you Stephen for supplying the band aid! We enjoyed this trip as much as last year and plan to stay with Stephan again.
Top guest favorite
An open living area is highlighted by high ceilings with exposed beams and large glass doors that provide a view of the meadow. Two comfortable sofas face each other across a central area rug, inviting relaxation. Light floods the space, enhancing its airy feel.
Guesthouse in West Tisbury
5 out of 5 average rating, 11 reviews

Beautiful + Airy MV Barn

LolaRating, 5 stars7 months ago
Our second time at the barn! Heaven. An absolute dream. Comfortable, quiet, clean and well appointed. We shall return. Thanks so much Amy.

Guest house rentals with a washer and dryer

A charming cottage is framed by vibrant gardens filled with blooming flowers in various hues. The building features a sloped roof and is surrounded by lush greenery, adding a serene touch to the overall setting.
Guesthouse in Edgartown
4.91 out of 5 average rating, 11 reviews

Beautiful Cottage in Private but Convenient Locale

DaveRating, 5 stars22 months ago
Rachel’s cottage is quite charming. Edgartown is easily accessible, yet the cottage is very private, ideal for a quiet getaway.
Superhost
A coastal view features gentle waves lapping against a rocky shore. Green vegetation lines the beach, with a lone tree positioned near the water's edge. The horizon shows a mix of land and sky, creating a serene coastal atmosphere.
Guesthouse in Falmouth
4.67 out of 5 average rating, 15 reviews

Woods Hole Cottage close to Beach and Village

KyleRating, 5 stars9 months ago
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.
A wooden deck extends from the upper level of the house, featuring a shaded umbrella. Sturdy stairs lead up to the deck, while a gravel pathway surrounds the property. The exterior showcases natural wood siding and is nestled among trees, enhancing the secluded atmosphere.
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.
Guest favorite
A spacious artist's studio is illuminated by natural light from multiple skylights and windows. The layout includes a comfortable king bed and a work area with tables and chairs, creating an inviting space for creativity. Warm wood accents complement the bright, airy atmosphere.
Guesthouse in West Tisbury
4.96 out of 5 average rating, 67 reviews

Vineyard Meadow Artist Studio

RinaRating, 5 stars2 weeks ago
Carlo's place was centrally located on the Vineyard, just a short drive from the various towns! The house is located on the edge of a wild life refuge, and is a beautiful, two mile walk from the beach. The apartment itself is comfortable and has all the essentials.
Top guest favorite
A stone pathway leads towards the entrance of the property, bordered by lush greenery and well-maintained hedges. A wooden fence stands to the right, with an American flag gently waving in the breeze. Bright blue sky adds to the inviting ambiance.
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.

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