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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 private bathroom
20–25 Sept
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4.92 out of 5 average rating, 209 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
4.95 out of 5 average rating, 191 reviews
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds, 1 bathroom
8–15 Aug
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, 83 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
4.98 out of 5 average rating, 53 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
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage w/ AC - Sleeps 8
3 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
4.33 out of 5 average rating, 3 reviews
Guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.95 out of 5 average rating, 212 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
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, 52 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
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, 146 reviews
Guest favourite
Flat in Oak Bluffs
14C Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 195 reviews
Top 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
4.93 out of 5 average rating, 14 reviews
Guest favourite
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
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
OB Salt & Cedar Cottage
4 bedrooms, 9 beds, 2 bathrooms
24–31 Aug
5.0 out of 5 average rating, 3 reviews