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 Edgartown
4.73 out of 5 average rating, 44 reviewsMarthas Vineyard 1BR Cottage 10 min to beach/town
Jun 9 – 16
Guesthouse in Vineyard Haven
4.94 out of 5 average rating, 125 reviewsWest Chop Cottage + Beach Access
Jun 9 – 16
Guesthouse in Falmouth
4.71 out of 5 average rating, 63 reviewsCOZY GUESTHOUSE
Jun 18 – 25
Guesthouse in Chilmark
4.96 out of 5 average rating, 77 reviewsBeautifully Renovated 1800s Chilmark Barn
Mar 22 – 29
Guest house rentals with a patio
Guesthouse in Edgartown
4.92 out of 5 average rating, 13 reviewsPrivate Two bedroom Katama cottage near Edgartown
Aug 30 – Sep 6
Guesthouse in Edgartown
5.0 out of 5 average rating, 4 reviewsMushroom Cottage
Oct 6 – 13
Guesthouse in Oak Bluffs
Fantastical Fishermen’s Cottage & private Garden
Jun 2 – 9
Guesthouse in Chilmark
5.0 out of 5 average rating, 14 reviewsRenovated Midcentury Modern Chilmark Guesthouse
Jan 2 – 9
Guesthouse in West Tisbury
5.0 out of 5 average rating, 4 reviewsBeautiful + Airy MV Barn
May 6 – 13
Guesthouse in Edgartown
5.0 out of 5 average rating, 5 reviewsPrivate cabin in Wildlife Habitat; near bus route
Feb 18 – 25
Guesthouse in Falmouth
5.0 out of 5 average rating, 5 reviewsFalmouth Heights Beach Cottage
Oct 6 – 13
Guesthouse in Edgartown
Beautiful Charming Edgartown Guesthouse 1 Bedroom
Mar 3 – 10
Guest house rentals with a washer and dryer
Guesthouse in Falmouth
4.67 out of 5 average rating, 12 reviewsWoods Hole Cottage close to Beach and Village
Apr 8 – 15
Guesthouse in Edgartown
4.97 out of 5 average rating, 35 reviewsQuiet, Pet Friendly, Close to Edgartown and Oak Bl
Sep 27 – Oct 4
Guesthouse in Tisbury
Escape to Bungalow 24 on MV!
Dec 13 – 20
Guesthouse in Edgartown
5.0 out of 5 average rating, 4 reviewsThe Birdhouse: new Edgartown apartment
Jan 6 – 13
Guesthouse in West Tisbury
5.0 out of 5 average rating, 12 reviewsGuest house over Garage
Dec 10 – 17
Guesthouse in Edgartown
4.9 out of 5 average rating, 10 reviewsBeautiful Cottage in Private but Convenient Locale
Feb 1 – 8
Guesthouse in West Tisbury
Quiet Mid-Island Retreat 3 miles from beach
May 26 – Jun 2
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