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 142 properties available
BR1 King en suite & hall bath with shower stall, 1st floorBR2 Queen, 2nd floorBR3 Double and twin bed, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with shower stall, 2nd floor(2)Twin beds, 3rd floor loft via ladderLaundry facilities, 1st floor
Oak Bluffs 8023
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Oak Bluffs
$5,000.00 - $12,000.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8023
Perfect location for your family beach getaway , just a short distance to the water, just a few blocks into town to enjoy the picturesque parks, board... Read More
June 2025
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BR1 Queen en suite with shower, 1st floorBR2 Queen en suite with tub/shower, 2nd floorBR3 (2)Bunk beds, 2nd floor
Oak Bluffs 8815
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Oak Bluffs
$6,800.00 - $9,000.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 8815
An extensive redesign and perhaps the most dramatic transformation yet! This wonderful downtown cottage has been restored in a way that reflects the c... Read More
June 2025
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BR1 Queen, 2nd floorHall bath with shower stall, 2nd floorBR2 King en suite with separate tub and shower, 2nd floorBR3 Queen, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floor
Oak Bluffs 819
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Oak Bluffs
$5,500.00 - $9,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 819
This neighborhood is the best kept secret with an Oak Bluffs address. Down a quiet road, yet on a road with easy access to Oak Bluffs, Edgartown, West... Read More
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BR1 Queen en suite with shower stall, 1st floorBR2 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs 8025
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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 Bedroom with AC split, First FloorBR2 Bunk Room Queen on the bottom, Twin on the top, AC split, First FloorBedrooms 1 and 2 share a Hall BathroomBR3 Queen Bedroom with a water view, Second FloorBR4 Queen Bedroom with a water view, Second FloorBR5 Queen Bedroom Second FloorBedrooms 3-5 share a Hall BathroomBR6 King Bedroom en-suite, Flat s
Oak Bluffs 8153
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Oak Bluffs
$20,000.00 / per week
Beds 6 beds
Baths 3 Full, 1 Half Bath
Sleeps 12 sleeps
Oak Bluffs 8153
This beautiful property located in the heart of Oak Bluffs has been completely renovated and boasts six spacious bedrooms. It features Altec surround ... Read More
June 2025
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BR1 King, 2nd floorBR2 Queen, 2nd floorHall bath with shower stall, 2nd floorHalf Bath and Laundry facilities, 1st floor
Oak Bluffs 8077
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Oak Bluffs
$3,800.00 - $5,000.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 4 sleeps
Rating 4.5 (2)
Oak Bluffs 8077
A classic Oak Bluffs Cottage has been renovated and revamped for 2023, adding air conditioning, a large sunroom and an additional half bath to this al... Read More
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BR1 Queen En Suite with Shower Stall, Second FloorBR2 Queen, Second FloorHall Bath with Shower Stall, Second FloorBR3 Queen, Second FloorBR4 (2) Bunk Beds, Second FloorHall Bath with Claw Foot Tub & French Shower, First FloorLaundry, First Floor
Oak Bluffs 8160
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Oak Bluffs
$6,500.00 - $8,500.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8160
Spend a relaxing afternoon rocking on the spacious front porch of this charming Victorian home, just moments from downtown Oak Bluffs, where you can e... Read More
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BR1 King En suite with Soaking Tub and Shower, First FloorBR2 Queen En suite with Shower Stall, First FloorBR3 Queen En suite with Shower Stall, First FloorBR4 Queen En suite with Shower Stall, First Floor
Oak Bluffs 8134
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Oak Bluffs
$23,000.00 - $24,000.00 / per week
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8134
A stunning four-bedroom home in one of the prestigious "Preserve" neighborhood in Oak Bluffs - perched on a hill overlooking the pond, the sprawling ... Read More
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BR1 Queen En Suite with Tub/Shower Combo, First FloorBR2 King, Second FloorBR3 (2)Twin beds, Second FloorHall bath with Tub/Shower Combo, Second Floor
Oak Bluffs 841
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Oak Bluffs
$4,500.00 - $8,475.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Oak Bluffs 841
Oak Bluffs off of County Road and close to the village, sits The Gladys Manor originally built in 1890. It has been exquisitely renovated as a three b... Read More
June 2025
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BR1 Queen, 2nd FloorBR2 (2) Twins, 2nd floorHall bath with tub/shower, 2nd Floor floorHall Bath with Tub/Shower combo and Washer/Dryer, 2nd FloorHalf Bath, 1st floor
Oak Bluffs 813
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Oak Bluffs
$3,645.00 - $3,780.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 4 sleeps
Rating 5 (1)
Oak Bluffs 813
This 2 story contemporary is located just outside Downtown Oak Bluffs with off-street parking for 2 cars. Immerse yourself in the hustle bustle of Cir... Read More
June 2025
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1 2 3 4 5 6 $3645 7
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BR1 Double, 2nd floorBR2 Double, 2nd floorHall bath with tub/shower, 1st floor
Oak Bluffs 8081
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Oak Bluffs
$4,000.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8081
Escape to a charming oasis in Oak Bluffs with this classic two-bedroom cottage, perfect for a relaxing vacation near beautiful Pay Beach, Inkwell, and... Read More
June 2025
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1 2 3 4 5 6 $4000 7
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BR1 King en suite with jacuzzi tub and shower, 1st floorBR2 King en suite with tub/shower, 2nd floorBR3 King en suite with tub/shower, 2nd floorBR4 (2)Queen beds en suite with tub/shower, lower level
Oak Bluffs 8107
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Oak Bluffs
$2,800.00 - $22,000.00 / per week
Beds 4 beds
Baths 7 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8107
Stunning waterfront home on the Lagoon with a private pool. You feel like you are wondering into paradise when you enter the front door. Truly a Vin... Read More
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