Guesthouse vacation rentals in Dukes County
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Top-rated guesthouse rentals in Dukes County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Dukes County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Chilmark
4.94 out of 5 average rating, 90 reviewsBeautifully Renovated 1800s Chilmark Barn
Guesthouse in Vineyard Haven
4.94 out of 5 average rating, 126 reviewsWest Chop Cottage + Beach Access
Guesthouse in Edgartown
5 out of 5 average rating, 21 reviewsTHE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 88 reviewsMermaid Cottage
Guesthouse in Chilmark
4.98 out of 5 average rating, 215 reviewsBeautiful Guest House in Chilmark
Guesthouse in Chilmark
4.99 out of 5 average rating, 92 reviews4-Season Guest House on Historic Chilmark Estate
Guesthouse in Tisbury
4.86 out of 5 average rating, 251 reviewsAdorable Vineyard Haven Cottage
Guesthouse in Falmouth
4.72 out of 5 average rating, 68 reviewsCOZY GUESTHOUSE
Guest house rentals with a patio
Guesthouse in Edgartown
5 out of 5 average rating, 3 reviewsBeautiful Charming Edgartown Guesthouse 1 Bedroom
Guesthouse in Edgartown
4.75 out of 5 average rating, 8 reviewsMushroom Cottage
Guesthouse in Edgartown
4.96 out of 5 average rating, 28 reviewsPrivate Two bedroom Katama cottage near Edgartown
Guesthouse in Edgartown
4.93 out of 5 average rating, 15 reviewsPrivate cabin in Wildlife Habitat; near bus route
Guesthouse in Oak Bluffs
4.89 out of 5 average rating, 9 reviewsCozy Vineyard Cottage
Guesthouse in Tisbury
4.97 out of 5 average rating, 75 reviewsKing bed, Stunning Water Views,AC,Near Bike Path
Guesthouse in West Tisbury
5 out of 5 average rating, 11 reviewsBeautiful + Airy MV Barn
Guest house rentals with a washer and dryer
Guesthouse in West Tisbury
New place to stayBright Summer Cottage
Guesthouse in Edgartown
4.96 out of 5 average rating, 50 reviewsQuiet, Pet Friendly, Close to Edgartown and Oak Bl
Guesthouse in Edgartown
4.91 out of 5 average rating, 11 reviewsBeautiful Cottage in Private but Convenient Locale
Guesthouse in Edgartown
5 out of 5 average rating, 5 reviewsGarden Gem: Cozy Guest House
Guesthouse in West Tisbury
4.94 out of 5 average rating, 18 reviewsGuest house over Garage
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