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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, 125 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage w/ AC - Sleeps 8
3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
New place to stay
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds, 2.5 bathrooms
29 Sept – 4 Oct
4.98 out of 5 average rating, 81 reviews
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
4.95 out of 5 average rating, 189 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
4.83 out of 5 average rating, 65 reviews
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 double beds, 1 bathroom
8–15 Aug
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
16–21 Oct
4.93 out of 5 average rating, 309 reviews
Guest favourite
Flat in Oak Bluffs
14B Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
16–21 Sept
4.98 out of 5 average rating, 51 reviews
Top 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, 424 reviews
Home in Edgartown
Peaceful get-a-way centrally located in Edgartown
4 bedrooms, 6 beds, 3 bathrooms
26–31 Jul
New place to stay
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.79 out of 5 average rating, 345 reviews
Top guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
4.92 out of 5 average rating, 145 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, 10 reviews
Guest favourite
Home in Oak Bluffs
Walk to Town, beach and amazing location 113A
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.95 out of 5 average rating, 209 reviews
Guest favourite
Home in Oak Bluffs
The Boat House
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.84 out of 5 average rating, 32 reviews
Guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
28 Aug – 4 Sept
4.92 out of 5 average rating, 13 reviews