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Display total before taxes

Search resultsOver 1,000 places

Superhost
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
Oct 9 – 14
$150 per night, originally $210
Superhost
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 double beds
Oct 13 – 18
$148 per night
Cottage in Oak Bluffs
Almost Paradise Charming two bedroom cottage
3 beds
Oct 9 – 14
$250 per night
Superhost
Home in Edgartown
Brand new gorgeous 2 bedroom guest house.
3 beds
Oct 29 – Nov 3
$180 per night, originally $200
Superhost
Room in Edgartown
Stay with Sara, Photography
The Alison Boylston Piazza House
Oct 22 – 27
$175 per night
Guesthouse in West Tisbury
Vineyard Meadow Artist Studio
3 beds
Oct 1 – 6
$125 per night, originally $140
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
6 beds
Oct 15 – 20
$299 per night, originally $499
Superhost
Apartment in Oak Bluffs
In-Town Retreat: Deck, Walk to beach, a Gem!
2 beds
Oct 29 – Nov 3
$155 per night
Cottage in Chilmark
Beautiful rustic cottage in the heart of Chilmark
3 beds
Oct 2 – 7
$308 per night
Superhost
Guest suite in West Tisbury
Studio Guest Suite in Modern Barn House
1 queen bed
Oct 16 – 21
$118 per night
Superhost
Cottage in Tisbury
Not Your Great Aunt's Island Cottage
5 beds
Oct 31 – Nov 5
$275 per night
Superhost
Apartment in Edgartown
The Osprey - Short walk to Edgartown & beach
2 beds
Oct 12 – 17
$211 per night
Superhost
Home in Oak Bluffs
Unique Luxury Yurt w/ Free kayaking
3 queen beds
Oct 8 – 13
$250 per night
Superhost
Home in Oak Bluffs
Walk to Town, beach and amazing location 113A
2 beds
Oct 9 – 14
$199 per night
Superhost
Home in Edgartown
Brand new, in-town mini Edgartown compound w/pool
7 beds
Oct 8 – 13
$1,100 per night
Superhost
Guesthouse in West Tisbury
Country cottage walk to Alley's General Store
1 bed
Oct 1 – 6
$150 per night
Superhost
Home in Edgartown
The Seashell Cove
4 beds
Oct 15 – 20
$270 per night, originally $720
Superhost
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
5 beds
Oct 22 – 27
$450 per night