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
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 19 – 26
Guesthouse in Chilmark
4.96 out of 5 average rating, 77 reviewsBeautifully Renovated 1800s Chilmark Barn
May 20 – 27
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 31 – Sep 7
Guesthouse in Edgartown
5.0 out of 5 average rating, 4 reviewsMushroom Cottage
Oct 7 – 14
Guesthouse in Oak Bluffs
Fantastical Fishermen’s Cottage & private Garden
Jun 3 – 10
Guesthouse in Chilmark
5.0 out of 5 average rating, 14 reviewsRenovated Midcentury Modern Chilmark Guesthouse
Oct 18 – 25
Guesthouse in West Tisbury
5.0 out of 5 average rating, 4 reviewsBeautiful + Airy MV Barn
May 7 – 14
Guesthouse in Edgartown
5.0 out of 5 average rating, 5 reviewsPrivate cabin in Wildlife Habitat; near bus route
Mar 23 – 30
Guesthouse in Falmouth
5.0 out of 5 average rating, 5 reviewsFalmouth Heights Beach Cottage
Sep 29 – Oct 6
Guesthouse in Edgartown
Beautiful Charming Edgartown Guesthouse 1 Bedroom
Mar 4 – 11
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 26 – May 3
Guesthouse in Tisbury
Escape to Bungalow 24 on MV!
Dec 15 – 22
Guesthouse in Edgartown
5.0 out of 5 average rating, 4 reviewsThe Birdhouse: new Edgartown apartment
Jun 2 – 9
Guesthouse in West Tisbury
5.0 out of 5 average rating, 12 reviewsGuest house over Garage
Dec 9 – 16
Guesthouse in Edgartown
4.9 out of 5 average rating, 10 reviewsBeautiful Cottage in Private but Convenient Locale
Feb 2 – 9
Guesthouse in West Tisbury
Quiet Mid-Island Retreat 3 miles from beach
May 26 – Jun 2
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