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Homes in Oak Bluffs
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Search results; Over 1,000 homes in Oak Bluffs
Over 1,000 homes in Oak Bluffs
Top guest favourite
Guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom
,
·
1 bed
,
·
0.5 private bathroom
25–30 Aug
25–30 Aug
$3,243 SGD
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for 5 nights
$3,243 SGD for 5 nights
,
·
4.9 out of 5 average rating, 145 reviews
4.9 (145)
Guest favourite
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
29 Sept – 4 Oct
29 Sept – 4 Oct
$5,623 SGD
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for 5 nights
$5,623 SGD for 5 nights
4.98 out of 5 average rating, 81 reviews
4.98 (81)
Guest favourite
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Aug
1–6 Aug
$10,366 SGD
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for 5 nights
$10,366 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom
1 bedroom
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
8–15 Aug
8–15 Aug
$13,062 SGD
Show price breakdown
for 7 nights
$13,062 SGD for 7 nights
Top guest favourite
Guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
3–8 Oct
3–8 Oct
$5,252 SGD
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for 5 nights
$5,252 SGD for 5 nights
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
30 Jul – 4 Aug
30 Jul – 4 Aug
$9,662 SGD
$6,788 SGD
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for 5 nights
4.97 out of 5 average rating, 29 reviews
4.97 (29)
Guest favourite
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$4,670 SGD
$3,253 SGD
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for 5 nights
4.79 out of 5 average rating, 345 reviews
4.79 (345)
Top guest favourite
Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$1,245 SGD
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for 5 nights
$1,245 SGD for 5 nights
4.95 out of 5 average rating, 424 reviews
4.95 (424)
Guest favourite
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
1 bathroom
1 bathroom
16–21 Oct
16–21 Oct
$2,577 SGD
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for 5 nights
$2,577 SGD for 5 nights
4.93 out of 5 average rating, 309 reviews
4.93 (309)
Home in Edgartown
Peaceful get-a-way centrally located in Edgartown
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
26–31 Jul
26–31 Jul
$4,059 SGD
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for 5 nights
$4,059 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
10–15 Oct
10–15 Oct
$3,301 SGD
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for 5 nights
$3,301 SGD for 5 nights
4.98 out of 5 average rating, 53 reviews
4.98 (53)
Superhost
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage w/ AC - Sleeps 8
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Jul
16–21 Jul
$5,419 SGD
Show price breakdown
for 5 nights
$5,419 SGD for 5 nights
New place to stay
New
Superhost
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
30 Jul – 4 Aug
30 Jul – 4 Aug
$7,489 SGD
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for 5 nights
$7,489 SGD for 5 nights
New place to stay
New
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$6,883 SGD
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for 5 nights
$6,883 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Flat in Tisbury
Vineyard Sweet Escape
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
18–23 Jul
18–23 Jul
$3,197 SGD
Show price breakdown
for 5 nights
$3,197 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2.5 bathrooms
2.5 bathrooms
19–24 Sept
19–24 Sept
$7,119 SGD
$5,058 SGD
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for 5 nights
4.92 out of 5 average rating, 144 reviews
4.92 (144)
Guest favourite
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
22–27 Jul
22–27 Jul
$4,289 SGD
$3,841 SGD
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for 5 nights
4.95 out of 5 average rating, 189 reviews
4.95 (189)
Home in Oak Bluffs
OB Salt & Cedar Cottage
4 bedrooms
4 bedrooms
,
·
9 beds
9 beds
,
·
2 bathrooms
2 bathrooms
24–31 Aug
24–31 Aug
$10,916 SGD
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for 7 nights
$10,916 SGD for 7 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Jul
16–21 Jul
$5,050 SGD
Show price breakdown
for 5 nights
$5,050 SGD for 5 nights
New place to stay
New
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