
Guesthouse vacation rentals in Dukes County
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Top-rated guesthouse rentals in Dukes County
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Family-friendly guest house rentals

Beautifully Renovated 1800s Chilmark Barn
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!

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!

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER
We had wonderful days at Big Chill. The cottage and main house is located very privately in a wooded area and surrounded by a beautiful garden, creating a magical space in nature. The cottage is very beautiful, bright, clean and has most things you need.We liked especially the upper floor where all beds were in one spacious room The cottage is entirely designed and built with care and character, craftsmanship, an artistic eye, and much heart by the hosts Kati and Mark. And they are ,as well ,very caring about their guests. They enjoy having guests and helping them, which creates a unique place where we felt very well and being in the right place.Thank you for creating such a nice place and sharing it with all your guests.

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!

Marthas Vineyard 1BR Cottage 10 min to beach/town
We really enjoyed our stay at this cottage. It was clean, comfortable, and close to town and the beach. Michael was an excellent host!
Guest house rentals with a patio

Beautiful Charming Edgartown Guesthouse 1 Bedroom
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!

Mushroom Cottage
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.

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
Our stay in Martha’s Vineyard was perfect. The Clamshell was beautifully decorated and was extremely clean - even better than the pictures. The location is outstanding and made it easy to come and go. We felt right at home during our visit. Nancy’s hospitality is unmatched.

Fantastical Fishermen’s Cottage & private Garden
A beautiful place in a lovely setting! We would definitely come back here again on our next visit to the Vineyard. Carolyn is one of the most responsive and helpful hosts we've had. A truly great stay.

Beautiful + Airy MV Barn
Our second time at the barn! Heaven. An absolute dream. Comfortable, quiet, clean and well appointed. We shall return. Thanks so much Amy.

Woods Hole Backyard Guest House Full of charm!
Guest house rentals with a washer and dryer

Quiet, Pet Friendly, Close to Edgartown and Oak Bl
Worth it, totally lived up to our hopes and expectations. Great house, perfect for a family (+dog) and was situated perfectly to get anywhere on the island. We had a wonderful time.

Beautiful Cottage in Private but Convenient Locale
Rachel’s cottage is quite charming. Edgartown is easily accessible, yet the cottage is very private, ideal for a quiet getaway.

Guesthouse
My family and I had a wonderful stay at Dilcelia and Marquissuel's Airbnb. The place was extremely clean and the yard was an added bonus! They were extremely responsive to all of our needs and a delight to work with. I would definitely recommend the property to anyone looking to stay on Martha's Vineyard.

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.

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.

Escape to Bungalow 24 on MV!
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.

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.

Bright Summer Cottage
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