Oak Bluffs

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 137 properties available
BR1 Queen en suite with shower stall, 1st floorBR2 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs
$1,750.00 - $4,500.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8025
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small... Read More
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BR1 Queen en suite with shower, 1st floorBR2 King and trundle en suite with tub/shower, 2nd floorBR3 Queen, 2nd floorQueen sofa bed sitting area, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorLaundry facilities, 1st floor
Oak Bluffs
$5,500.00 - $6,000.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 893
A classic Vineyard home close to Lagoon pond! This stylish and modern home includes space to roam throughout. This home includes an open floor plan wi... Read More
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BR1 King En Suite with Tub Shower Combo, Second FloorBR2 Queen & Daybed Trundle Adjoining Bath, First FloorAdjoining Bath with Tub Shower Combo, First FloorBR3 Queen & Double Sofabed Adjoining Bath, First FloorPowder Room, Second FloorKing, Second Floor Guest HouseBath with Shower Stall, Second Floor Guest HouseQueen, First Floor Guest HouseBath wi
Oak Bluffs
$12,500.00 - $15,000.00 / per week
Beds 5 beds
Baths 5 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8010
A Frank Lloyd Wright-inspired home in Harthaven with a reverse style 3-bedroom main house and a 2-bedroom guest house offers an abundance of privacy a... Read More
June 2025
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1 2 3 4 5 6 $12500 7
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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
Hot HOT 18
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 Queen, en Suite with shower, 1st floorBR2 Queen with adjoining bath of tub shower combo, 2nd floorBR3 (2) twin over double bunks, with adjoining bath of tub shower combo, 2nd floorBR4 (2) twins with adjoining bath with shower, 2nd floorPowder room, 1st floorLaundry facilities, 1st floor
Oak Bluffs
$6,950.00 - $11,750.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 8092
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the rig... Read More
June 2025
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BR1 Queen, 1st floorBR2 (2)Twin beds, 1st floorBR3 Queen, 1st floorHall bath with tub/shower, 1st floorLaundry facilities, 1st floorHalf bath, 2nd floor all bedrooms are located on the lower level.
Oak Bluffs
$3,500.00 - $4,000.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Rating 5 (2)
Oak Bluffs 8011
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
June 2025
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BR1 Queen, 1st floorHall bath with tub/shower with access to BR1, 1st floorBR2 Queen and twin bed, 2nd floorBR3 (2)Twin beds- can convert to king, 2nd floor loftHall bath with tub/shower, 2nd floor
Oak Bluffs Pet Friendly
$6,160.00 - $6,650.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 7 sleeps
Oak Bluffs 823
Modern contemporary cottage nestled in landscaped surroundings. Experience the best that Martha's Vineyard has to offer with wonderful privacy and mi... Read More
June 2025
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BR1 King en suite with separate tub and shower, 1st floorBR2 King en suite with shower, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorLaundry facilities, 1st floorHalf bath, 1st floor
Hot HOT 10
Oak Bluffs
$12,000.00 - $22,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8141
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
June 2025
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1 2 3 4 5 6 $12000 7
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    1 2 3 4 $16000 5
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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 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 with tub/shower, 1st floorBR2 Queen en suite with tub and shower, 1st floorBR3 Queen en suite with tub/shower, 2nd floorBR4 (2)Queen beds and twin en suite with shower stall, 2nd floor
Hot HOT 10
Oak Bluffs
$6,500.00 - $15,500.00 / per week
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps 11 sleeps
Oak Bluffs 8151
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
June 2025
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1 2 3 4 5 6 $7500 7
8 9 10 11 12 13 $9500 14
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    1 2 3 4 $14500 5
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BR1 King en suite with shower stall, 1st floorBR2 King en suite with tub/shower, 1st floorBR3 Queen and (2)Twin beds en suite with shower stall, lower levelGuest House: BR4 King, 1st floorBR5 (2)Twin beds, 1st floorHall bath with shower stall, 1st floorLaundry facilities, main house lower level
Oak Bluffs
$10,000.00 - $18,000.00 / per week
Beds 5 beds
Baths 4 Full Bath
Sleeps 12 sleeps
Rating 4 (1)
Oak Bluffs 8111
Oak Bluffs waterfront Main and Guest house with plenty of room to spread out and find your own peace and tranquility while you enjoy the spectacular v... Read More
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BR1 King, First FloorBR2 (2) Twin Beds, First FloorHall Bath with Tub/Shower, First Floor
Oak Bluffs
$2,500.00 - $2,800.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8021
Charming and pristine cottage nestled just over a mile from both Oak Bluffs Beaches and the vibrant town of Oak Bluffs, home to the country's oldest c... Read More
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