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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Apartment in Oak Bluffs
113B Cutest! Walk to Beach, Town and Harbor!
1 bedroom, 1 bed, 1 private bathroom
19–24 Aug
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4.9 out of 5 average rating, 269 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
30 Aug – 4 Sept
New place to stay
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds
5–10 Sept
New place to stay
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds
29 Sept – 4 Oct
4.83 out of 5 average rating, 66 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
19–24 Oct
4.93 out of 5 average rating, 316 reviews
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds
21–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
16–21 Oct
4.98 out of 5 average rating, 55 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds
13–18 Sept
4.95 out of 5 average rating, 194 reviews
Top guest favourite
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 Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds
8–13 Sept
4.96 out of 5 average rating, 130 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
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, 427 reviews
Guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds
26–31 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oak Bluffs
Charming 3-Bedrm w/Loft.New Construct! Walk 2 town
3 bedrooms, 5 beds
22–29 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds
13–18 Sept
4.97 out of 5 average rating, 184 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 7 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, 53 reviews
Guest favourite
Home in Oak Bluffs
Sunny 3-bed close to beach and town
3 bedrooms, 3 beds
9–14 Jul
4.91 out of 5 average rating, 32 reviews