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Search results; Over 1,000 homes in Oak Bluffs
Over 1,000 homes in Oak Bluffs
Guest favourite
Guest favourite
Home in Oak Bluffs
The quintessential MV home. Plan your 2026 escape!
4 bedrooms
,
·
7 beds
,
·
4 private bathrooms
21–26 Sept
21–26 Sept
$6,302 SGD
Show price breakdown
for 5 nights
$6,302 SGD for 5 nights
,
·
4.89 out of 5 average rating, 37 reviews
4.89 (37)
Home in Tisbury
The Bird House
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
8–14 Aug
8–14 Aug
$20,596 SGD
$17,032 SGD
Show price breakdown
for 6 nights
Free cancellation
New place to stay
New
Home 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
$10,959 SGD
Show price breakdown
for 7 nights
$10,959 SGD for 7 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$5,857 SGD
Show price breakdown
for 5 nights
$5,857 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Top guest favourite
Guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
16–21 Aug
16–21 Aug
$10,737 SGD
$9,505 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 213 reviews
4.95 (213)
Top guest favourite
Guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
5.5 bathrooms
5.5 bathrooms
4–9 Oct
4–9 Oct
$4,376 SGD
Show price breakdown
for 5 nights
$4,376 SGD for 5 nights
4.93 out of 5 average rating, 221 reviews
4.93 (221)
Top 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
$2,583 SGD
Show price breakdown
for 5 nights
$2,583 SGD for 5 nights
4.93 out of 5 average rating, 313 reviews
4.93 (313)
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
23–28 Aug
23–28 Aug
$5,839 SGD
Show price breakdown
for 5 nights
$5,839 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
$1,248 SGD
Show price breakdown
for 5 nights
$1,248 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 426 reviews
4.95 (426)
Guest favourite
Guest favourite
Cottage in Oak Bluffs
111G Beautiful walk to Town, Inkwell and harbor!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
24–29 Aug
24–29 Aug
$4,863 SGD
Show price breakdown
for 5 nights
$4,863 SGD for 5 nights
4.94 out of 5 average rating, 222 reviews
4.94 (222)
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
29 Aug – 3 Sept
29 Aug – 3 Sept
$4,490 SGD
$3,869 SGD
Show price breakdown
for 5 nights
Free cancellation
4.79 out of 5 average rating, 347 reviews
4.79 (347)
Top guest favourite
Guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,337 SGD
Show price breakdown
for 5 nights
$1,337 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 139 reviews
4.94 (139)
Home in Oak Bluffs
Charming 3BR Cottage Near the Beach w/ Deck
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$4,304 SGD
Show price breakdown
for 5 nights
$4,304 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Oak Bluffs
Beautiful Home in Oak Bluffs Center!
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
16–21 Sept
16–21 Sept
$4,558 SGD
Show price breakdown
for 5 nights
$4,558 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 47 reviews
5.0 (47)
Top guest favourite
Guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Sept
20–25 Sept
$2,768 SGD
$2,284 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 302 reviews
4.97 (302)
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
$10,038 SGD
Show price breakdown
for 7 nights
$10,038 SGD for 7 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Sept
13–18 Sept
$4,102 SGD
Show price breakdown
for 5 nights
$4,102 SGD for 5 nights
4.95 out of 5 average rating, 193 reviews
4.95 (193)
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$7,448 SGD
Show price breakdown
for 5 nights
$7,448 SGD for 5 nights
Free cancellation
New place to stay
New
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,997 SGD
Show price breakdown
for 5 nights
$1,997 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
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