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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
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4.96 out of 5 average rating, 123 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 423 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
4.88 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
8–15 Jul
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 307 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Cabin in Edgartown
Nice little cabin close to downtown Oak Bluffs
New place to stay, 1 bed, 1 bathroom
5–10 Jul
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 1 bathroom
16–21 Sept
Top guest favourite
Flat in Oak Bluffs
Beautiful and Short walk beach, town and harbor!
4.93 out of 5 average rating, 81 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Jul
Guest favourite
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Jul
Guest house in Oak Bluffs
Charming guesthouse in OB
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
4.97 out of 5 average rating, 131 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
4.94 out of 5 average rating, 511 reviews, 2 beds, 1 bathroom
27 Sept – 2 Oct
Home in Oak Bluffs
East Chop Oceanview Escape
5.0 out of 5 average rating, 4 reviews, 6 bedrooms, 8 beds, 4.5 bathrooms
5–11 Jul
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
4.9 out of 5 average rating, 104 reviews, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
4.96 out of 5 average rating, 25 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Jul
Top guest favourite
Apartment in Oak Bluffs
FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
4.95 out of 5 average rating, 186 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
9–14 Jul
Top guest favourite
Flat in Oak Bluffs
OB Apartment-Full Kitchen/Laundry/Outdoor Shower
5.0 out of 5 average rating, 37 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Jul
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
4.92 out of 5 average rating, 65 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul