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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 beds, 1 private bathroom
19–24 Oct
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4.93 out of 5 average rating, 316 reviews
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 221 reviews
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Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds
3–8 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
8 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
18–23 Oct
4.95 out of 5 average rating, 432 reviews
Guest favourite
Home in Oak Bluffs
Sunny 3 bedroom with large deck, porch & kayaks
3 bedrooms, 5 beds
4–11 Jun
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds
21–27 Aug
5.0 out of 5 average rating, 5 reviews
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Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
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Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 32 reviews
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Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
16–21 Oct
4.97 out of 5 average rating, 59 reviews
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed
22–27 Aug
4.98 out of 5 average rating, 203 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Home in Oak Bluffs
*NEW* 3 min drive to OB Circuit ave
5 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
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Home in Oak Bluffs
Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
3 bedrooms, 3 beds
23–28 Aug
4.95 out of 5 average rating, 44 reviews
Home in Edgartown
Peaceful get-a-way centrally located in Edgartown
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Oak Bluffs
Beautiful Home in Oak Bluffs Center!
3 bedrooms, 6 beds
16–21 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Oak Bluffs
Walk East Chop from Dover House
5 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 34 reviews