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 139 properties available
BR1 King En Suite with Shower Stall and Tub, First FloorBR2 King En Suite with Shower Stall, Second FloorBR3 Queen En Suite with Shower Tub Combo, Second FloorBR4 Queen En Suite with Shower Stall, Second FloorAdditional Sleeping: Queen Murphy Bed, Lower LevelTwo Sofabeds, Second Floor
Oak Bluffs
$3,000.00 - $15,000.00 / per week
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 817
Welcome to Mermaid's Grotto, located just under a mile from the heart of Oak Bluffs. As you step inside, you'll find an open concept living space that... Read More
June 2025
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BR1 King en suite with shower stall, 2nd floorBR2 Queen, 1st floorBR3 Queen, 1st floorBR4 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorHalf bath, 2nd floorLaundry facilities, 1st floor
Oak Bluffs
$7,000.00 - $16,500.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8104
Lovely waterfront bungalow on the Lagoon in Oak Bluffs. This pristine Martha's Vineyard property offers a shared dock, mooring and private beach. View... Read More
June 2025
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1 2 3 4 5 6 $7000 7
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15 16 17 18 19 20 $8500 21
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BR1 Queen En Suite with Shower Stall, Second FloorBR2 (2) Double Beds En Suite with Shower Tub Combo, Second FloorPowder Room, First Floor
Oak Bluffs
$2,800.00 - $8,400.00 / per week
Beds 2 beds
Baths 2 Full, 1 Half Bath
Sleeps 4 sleeps
Oak Bluffs 8167
Experience the charm of Oak Bluffs in our delightful 2-bedroom cottage, perfectly situated in the heart of downtown. Both bedrooms, located on the sec... Read More
June 2025
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1 2 3 4 5 6 $3850 7
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20 21 22 23 24 25 $6020 26
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10 11 12 13 14 15 $8400 16
17 18 19 20 21 22 $5000 23
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BR1 Queen, 1st floor hall bath of shower, BR2 (2)Twin beds, 2nd floorBR3 Queen, 2nd floor hall bath of tub/shower combo BR4 King, 2nd floor, en suite with separate tub and separate shower, 2nd floor
Hot HOT 19
Oak Bluffs
$7,000.00 - $10,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 811
Prepare to be mesmerized by the awe-inspiring sunsets visible from the large wraparound deck and several rooms of this immaculate Oak Bluffs home. Boa... Read More
June 2025
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1 2 3 4 5 6 $7000 7
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17 18 19 20 21 22 $7750 23
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BR1 Queen en suite with shower stall, 1st floorBR2 Queen, 1st floorHall bath with shower stall, 1st floorBR3 (2)Double beds en suite with shower stall, 2nd floorBR4 Queen, 2nd floorHall bath with shower stall, 2nd floorBR5 King en suite with shower stall, 2nd floor
Oak Bluffs
$18,825.00 / per week
Beds 5 beds
Baths 5 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8814
A stunning five bedroom bungalow overlooking Nantucket Sound, with an expansive porch offering one of the greatest views on the Island. Inside, the ho... Read More
June 2025
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BR1 Queen en suite with tub and french shower, 1st floorBR2 Queen, 2nd floorBR3 Queen, 2nd floorHall bath with shower stall, 2nd floorGuest quarters: BR4 (2)Twin beds, 2nd floorHall bath with shower stall, 2nd floorSleep sofa, 1st floor
Oak Bluffs
$4,400.00 - $12,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Rating 3 (1)
Oak Bluffs 829
The J. A. Norton House has all the vintage charm of the 1870's but offers every summer vacationer's dream for modernity, convenience, and enjoyment. L... Read More
June 2025
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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
$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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15 16 17 18 19 20 $6000 21
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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
$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 King en suite shower stall, 2nd floorBR2 Queen, 1st floorBR3 Queen,1st floorBR4 Daybed, 2nd floorGuest house: BR5 (2)Twin beds en suite with shower stall, 1st floorhall bath first floor
Oak Bluffs
$10,000.00 - $21,000.00 / per week
Beds 5 beds
Baths 3 Full Bath
Sleeps 9 sleeps
Oak Bluffs 8154
Enjoy high end living, with commanding water views and Vineyard Haven beyond while living in this luxurious and meticulously detailed home with guest ... Read More
June 2025
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BR1 Queen, First FloorHall Bath with Shower Tub Combo, First FloorBR2 Queen, Second FloorPowder Room, Second FloorBR3 Bunk Bed, Second Floor
Oak Bluffs Pet Friendly
$2,100.00 - $8,500.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Oak Bluffs 8139
Welcome to your perfect getaway at this beautifully renovated cottage in Oak Bluffs, Martha's Vineyard. This cottage features three bedrooms, making i... 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 Tub & Shower Stall, Second FloorBR2 Queen, Second FloorHall Bath with Shower Stall, Second FloorBR3 Queen, Second FloorBR4 Twin Trundle, Second FloorHall Bath with Tub Shower Combo, First Floor
Oak Bluffs
$8,000.00 - $11,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 800
A beautiful four-bedroom home in highly desirable Harthaven - great proximity to downtown Oak Bluffs, State Beach and so much more! Designed with comf... Read More
June 2025
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1 2 3 4 5 6 $8000 7
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17 18 19 20 21 22 $10000 23
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BR1 Queen En Suite with Shower Stall, Second FloorBR2 Double, Second FloorBR3 (2) Twin Beds, Second FloorHall Bath with Tub/Shower Combo, Second FloorTwin Sofa Bed, Living RoomPowder Room, First FloorLaundry Facilities, First Floor
Oak Bluffs
$4,500.00 - $8,500.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Oak Bluffs 803
Oak Bluffs! Ready for your summer vacation! Beautifully furnished in a casually elegant style, this home allows you room to relax with friends and fam... Read More
June 2025
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1 2 3 4 5 6 $5000 7
8 9 10 11 12 13 $5000 14
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22 23 24 25 26 27 $6500 28
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17 18 19 20 21 22 $8500 23
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