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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 137 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 434 reviews
Top guest favourite
Home in Oak Bluffs
Beachfront Victorian Oasis Welcome to One
10 bedrooms, 11 beds, 4.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
3–8 Oct
4.89 out of 5 average rating, 19 reviews
Guest favourite
Home in Oak Bluffs
Beach home just 0.8 miles to Farm Neck Golf Club!
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.79 out of 5 average rating, 140 reviews
Guest favourite
Cottage in Oak Bluffs
#Islandbeachrose. Walk To Beach and Town!
4 bedrooms, 6 beds, 2 bathrooms
6–13 Sept
4.93 out of 5 average rating, 27 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, 322 reviews
Top guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Oak Bluffs
Fantastic beach Ap 0.8 miles from Farm Neck Golf!
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.72 out of 5 average rating, 176 reviews
Home in Oak Bluffs
Charming 3BR Cottage Near the Beach w/ Deck
3 bedrooms, 4 beds, 1 bathroom
3–9 Sept
Superhost
Home in Oak Bluffs
Stunning OB retreat mins from best attractions
5 bedrooms, 8 beds, 3.5 bathrooms
28 Sept – 3 Oct
New place to stay
Top guest favourite
Home in Oak Bluffs
Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 45 reviews
Guest favourite
Cottage in Oak Bluffs
111G Beautiful walk to Town, Inkwell and harbor!
1 bedroom, 2 beds, 1.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 227 reviews
Guest favourite
Home in Oak Bluffs
The Lighthouse
3 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 161 reviews
Guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Home in Oak Bluffs
Relaxing oasis in center of Oak Bluffs
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 43 reviews
Guest favourite
Home in Oak Bluffs
Renovated Downtown Charmer, 3 Blocks to the Beach
3 bedrooms, 7 beds, 2 bathrooms
17–24 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Oak Bluffs
*NEW* 3 min drive to OB Circuit ave
5 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews