
Guesthouse vacation rentals in Dukes County
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Top-rated guesthouse rentals in Dukes County
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Popular amenities for Dukes County guesthouse rentals
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Guest favorite

Guesthouse in Chilmark
4.94 out of 5 average rating, 90 reviewsBeautifully 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

Guesthouse in Vineyard Haven
4.94 out of 5 average rating, 126 reviewsWest 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 reviewsMarthas 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

Guesthouse in Edgartown
5 out of 5 average rating, 21 reviewsTHE 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

Guesthouse in Edgartown
5 out of 5 average rating, 3 reviewsBeautiful 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 reviewsMushroom 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

Guesthouse in Edgartown
4.93 out of 5 average rating, 15 reviewsPrivate 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

Guesthouse in Oak Bluffs
4.89 out of 5 average rating, 9 reviewsCozy 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 reviewsKing 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

Guesthouse in West Tisbury
5 out of 5 average rating, 11 reviewsBeautiful + 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

Guesthouse in Edgartown
4.91 out of 5 average rating, 11 reviewsBeautiful 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

Guesthouse in Falmouth
4.67 out of 5 average rating, 15 reviewsWoods 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.

Guesthouse in West Tisbury
4.94 out of 5 average rating, 18 reviewsGuest 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

Guesthouse in West Tisbury
4.96 out of 5 average rating, 67 reviewsVineyard 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

Guesthouse in Tisbury
5 out of 5 average rating, 7 reviewsEscape 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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- Brown University
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Roger Williams Park Zoo
- Oakland Beach
- Grey's Beach
- Coast Guard Beach
- Scusset Beach
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Chapin Memorial Beach
- Earle Road Beach
- Fort Adams State Park
- Rocky Point Beach
- Agawam Hunt
- Surfside Beach
- Pilgrim Beach
- Springhill Beach
- Englewood Beach
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