Oak Bluffs

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Oak Bluffs - or 'OB' - is a classic beach town, filled with tons of fun! Enjoy the sandy beaches along the calm waters of Nantucket Sound, events held in Ocean Park and the Tabernacle, and the casual atmosphere of the harbor and Circuit Avenue. Popular attractions include the Flying Horses Carousel, the nation’s oldest operating platform carousel, and the Martha’s Vineyard Camp Meeting Association, a National Historic Landmark and community of over 300 charming Victorian gingerbread cottages surrounding a beautiful iron Tabernacle. Circuit Avenue is always bustling and has something for everyone – ice cream, coffee shops, eateries, bars and boutiques. The Harbor is entirely walkable and is a great place to relax and watch the boats coming and going. Outside of the downtown area, there are many areas in OB that offer a quieter atmosphere. Contact us and we'll help you find the perfect getaway!


Properties Available 136 properties available
BR1 King en suite with tub/shower, 1st floorBR2 Queen en suite with separate tub and shower, 2nd floorBR3 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorQueen sofa bed, 2nd floor denBR4 Queen en suite with shower stall, lower levelHalf bath, 1st floorGuest house: BR5 Queen, 1st floorHall bath with shower stall, 1st floorBR6 Queen en sui
Oak Bluffs Main and Guest 8017
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Oak Bluffs
$8,500.00 - $22,000.00 / per week
Beds 6 beds
Baths 6 Full, 1 Half Bath
Sleeps 14 sleeps
Rating 5 (1)
Oak Bluffs Main and Guest 8017
ONLY A FIVE MINUTE WALK TO OAK BLUFFS CENTER! On the outskirts of the infamous Oak Bluffs gingerbread cottages, this home mimics the architecture but ... Read More
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BR1 Queen, 1st floorHall bath with tub/shower, 1st floorBR2 (2)Twin beds, 2nd floorBR3 Queen, 2nd floorHall bath with tub/shower, 2nd floorBR4 Queen, 2nd floor loftHall bath with tub/shower, 2nd floor loft
Oak Bluffs 8170
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Oak Bluffs
$16,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8170
Easy breezy summer living in this fresh and beautifully renovated, airy cape. Designed with a relaxed modern vibe, this house forces you to have a rel... Read More
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BR1 King en suite with separate shower and soaking tub, 1st floorBR2 Queen en suite with tub/shower, 2nd floorBR3 Queen en suite with shower stall, 2nd floorBR4 Double en suite with tub and french shower, 2nd floorBR5 (2)Twin beds en suite with tub/shower, 2nd floor (over the garage with private entrance)Half baths, 1st and 2nd floorsLaundry facili
Oak Bluffs 846
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Oak Bluffs
$14,500.00 - $32,025.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 846
The "Preserve" off of County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Re... Read More
June 2025
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1 2 3 4 5 6 $22500 7
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BR 1 Queen, 2nd floor BR 2 Queen, 2nd floor BR 3 Two Twins, loft/3rd floor All bedrooms share hall bath with shower, 1st and 2nd floor
Hot HOT 11
Oak Bluffs Condo 8015
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Oak Bluffs
$4,000.00 - $5,000.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Oak Bluffs Condo 8015
Sengekontacket Association offers a charming residential community with convenient access to tennis courts and a picturesque pond, all just a short di... Read More
June 2025
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BR1 King en suite with tub/shower, 1st floorBR2 (2)Twin beds 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs 8093
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Oak Bluffs
$2,800.00 - $4,900.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8093
Two bedroom beachfront condominium with views of Nantucket Sound. Ocean views from almost every room. Just moments from Oak Bluffs town beach and a sh... Read More
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BR1 Queen en suite with tub/shower, 1st floorBR2 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs 835
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Oak Bluffs
$1,900.00 - $5,100.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Rating 4.5 (2)
Oak Bluffs 835
Welcome to this charming two bed, two bath corner end unit condo located in the heart of Oak Bluffs, just steps away from the Town Beach (Ink Well). E... Read More
June 2025
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BR1 Double, First FloorBR2 Double Sofa Bed with Split Mattress, First FloorHall bath with Shower, First FloorLaundry, First Floor
Oak Bluffs 8044
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Oak Bluffs
$2,500.00 - $2,800.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8044
Newly constructed guesthouse with all the amenities of a Vineyard vacation home. Two bedrooms with shared hall bathroom. Fully equipped eat-in kitch... Read More
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BR1 King en suite with shower and tub, 1st floorBR2 King en suite with shower, 1st floorBR3King en suite with shower, 2nd floorBR4 (2) Twins with hall bath, 2nd floor
Oak Bluffs 824
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Oak Bluffs Pet Friendly
$5,000.00 - $15,800.00 / per week
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 824
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon waterfront of Oak Bluffs, Massachusetts, and offer... Read More
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BR1 Queen En Suite, Second FloorBR2 Queen En Suite, First FloorBR3 Queen & Twin Sofabed, Second FloorBR4 Queen, Second Floor BR5 (2) Twin Beds En Suite, Lower Level
Oak Bluffs 845
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Oak Bluffs
$5,250.00 - $16,500.00 / per week
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 11 sleeps
Oak Bluffs 845
Newly constructed home ideally located just over a mile from the center of downtown Oak Bluffs in pristine condition. Enjoy three levels of stylish li... Read More
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BR1 Queen en suite with shower, 1st floorHall bath with tub/shower & laundry, 1st floorBR2 Queen, 2nd floorBR3 (2)Twin beds, 2nd floor
Hot HOT 26
Oak Bluffs 8103
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Oak Bluffs
$3,500.00 - $6,400.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 4.5 (2)
Oak Bluffs 8103
A charming three bedroom cottage in Oak Bluffs. Features an open concept living, kitchen and dining area on the first floor. One bedroom en-suite on t... Read More
June 2025
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1 2 3 4 5 6 $3500 7
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br>Guest apartment: BR5 Queen, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorHall bath with shower stall, lower level
Oak Bluffs 8106
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Oak Bluffs
$7,000.00 - $16,500.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 8106
The Weku House is a luxurious, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha's Vineyard. Elegantly decorated with desi... Read More
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BR1 Double, 1st floorHall bath with shower stall, 1st floorBR2 Queen, 2nd floorBR3 Double and twin, 2nd floorHall bath with tub/shower, 2nd floor
Oak Bluffs 850
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Oak Bluffs Pet Friendly
$3,800.00 - $5,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Oak Bluffs 850
Escape to a cozy and well-maintained three-bedroom Oak Bluffs cottage, located on a peaceful street just a short stroll from the harbor and all the vi... Read More
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