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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.98 out of 5 average rating, 197 reviews
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
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
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 double beds, 1 bathroom
8–15 Aug
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 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
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
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 Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
New place to stay
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
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
2 bedrooms, 2 beds, 1.5 bathrooms
30 Jul – 4 Aug
New place to stay
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, 144 reviews
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
1 bedroom, 2 beds, 1.5 bathrooms
29 Jul – 3 Aug
4.95 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Oak Bluffs
Beautiful and Short walk beach, town and harbor!
1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
4.93 out of 5 average rating, 83 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
New place to stay
Guest favourite
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 9 reviews
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews