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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
Waterview, Private, Walk to Beach, Mile to Town
2 bedrooms, 4 beds, 1.5 private bathrooms
14–19 Sept
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4.83 out of 5 average rating, 217 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 221 reviews
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds, 4.5 bathrooms
21–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 428 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 316 reviews
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
8 bedrooms, 10 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 12 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 bathrooms
27 Sept – 2 Oct
New place to stay
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Oct
4.98 out of 5 average rating, 56 reviews
Guest favourite
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds, 1.5 bathrooms
18–23 Sept
4.97 out of 5 average rating, 186 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.82 out of 5 average rating, 67 reviews
Guest favourite
Cottage in Oak Bluffs
#Islandbeachrose. Walk To Beach and Town!
4 bedrooms, 6 beds, 2 bathrooms
6–13 Sept
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 131 reviews
Flat in Oak Bluffs
Charming 3 Bedroom Apartment
4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug