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 139 properties available
BR1 Double, 1st floorHall bath with shower stall, 1st floorHalf bath, 1st floorLaundry facilities, 1st floorBR2 King, 2nd floorBR3 Queen, 2nd floorBR4 Queen and (2)twin beds, 2nd floorHall bath with soaking tub only, 2nd floor
Oak Bluffs 834
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Oak Bluffs
$6,800.00 - $18,900.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 9 sleeps
Oak Bluffs 834
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear. ... Read More
June 2025
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1 2 3 4 5 6 $9200 7
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BR1 King En Suite with Shower Stall and Tub, First FloorBR2 (2) Twin Beds, First FloorBR3 Queen, First FloorHall Bath with Tub Shower Combo, First FloorBR4 Pull out Sofa Bed, Den First FloorOverflow: (2) Twin Beds, Lower LevelHall Bath with Shower Stall, Lower LevelSleeper Sofa, Lower Level
Oak Bluffs 8108
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Oak Bluffs
$4,000.00 - $6,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8108
Nestled in the highlands of East Chop, this updated home offers the perfect blend of convenience and tranquility for your Vineyard vacation. Within mi... Read More
June 2025
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1 2 3 4 5 6 $4000 7
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17 18 19 20 21 22 $6000 23
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BR1 King en Suite with Tub/Shower combo 2nd floorBR2 Queen, 2nd floorHall Bath of Tub/Shower Combo 2nd floorBR3 Queen, 1st floorAdditional sleeping Sunroom (2) Twins, 1st floorFull hall bath, 1st floorLaundry 1st floor
Oak Bluffs 8115
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Oak Bluffs
$6,500.00 - $8,000.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8115
Spacious Colonial in Meadowview Farms with room for everyone to spread out. The well equiped kitchen and indoor dining area open to the expansive re... Read More
June 2025
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1 2 3 4 5 6 $6500 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 Queen, 1st floorBR2 (2) Twin beds, 1st floorHall bath with shower stall, 1st floorBR3 King, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with shower, 2nd floorBonus: (2) Trundle beds, kid's loftLaundry facilities, 1st floor
Hot HOT 18
Oak Bluffs 8169
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Oak Bluffs Pet Friendly
$3,500.00 - $4,000.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 5 (9)
Oak Bluffs 8169
Cozy Cottage at Coleman Corners is located on a quiet, peaceful road in the East Chop Highlands of Oak Bluffs, away from the hustle and bustle, yet on... Read More
June 2025
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1 2 3 4 5 6 $3500 7
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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 King En Suite with Shower Stall, First FloorBR2 Queen, First FloorHall Bath with Tub Shower Combo, First FloorBR3 (2) Twin Beds, First FloorPowder Room, First FloorOverflow: Queen over Queen & Twin XL over Twin XL Bunk Bed, Lower LevelHall Bath with Shower Stall, Lower Level
Oak Bluffs 840
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Oak Bluffs
$3,000.00 - $7,500.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 840
This rental house is a contemporary and inviting home that combines modern amenities with a cozy Cape feel. The spacious and open concept living area ... Read More
June 2025
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1 2 3 4 5 6 $5000 7
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17 18 19 20 21 22 $7500 23
24 25 26 27 28 29 $6300 30
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BR1 Queen en suite with shower stall, AC 1st floorBR2 Twin bed, 1st floorHall bath with tub, 1st floorBR3 (2)Twin beds, 2nd floorBR4 Queen, 2nd floorBR5 Queen, 2nd floorHall bath with tub/shower, 2nd floor
Oak Bluffs 8124
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Oak Bluffs
$7,500.00 / per week
Beds 5 beds
Baths 3 Full Bath
Sleeps 9 sleeps
Rating 3 (1)
Oak Bluffs 8124
Charming five bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Birds eye view of all that is happ... Read More
June 2025
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BR1 Queen en suite with tub/shower, 3rd floorBR2 (2)Twin beds, 1st floorBR3 (2)Double beds, 1st floorHall bath with tub/shower, 1st floorLaundry facilities, 1st floorHalf bath, 2nd floor
Oak Bluffs Condo 8064
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Oak Bluffs
$3,295.00 - $5,995.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs Condo 8064
Multi-level condominium unit overlooking Sengekontacket Pond and beyond in Oak Bluffs. Association pool and tennis courts. Deck and patio areas for yo... Read More
June 2025
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1 2 3 4 5 6 $4675 7
8 9 10 11 12 13 $4950 14
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22 23 24 25 26 27 $5995 28
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BR1 King En Suite with Shower Stall, Second FloorBR2 Queen, Second FloorHall Bath with Tub/Shower Combo, Second FloorBR3 (2) Double Beds, Second FloorPowder Room, First Floor
Oak Bluffs 8063
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Oak Bluffs
$3,500.00 - $6,500.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8063
Nestled in a quiet area of Oak Bluffs, yet convenient to all areas of the island, this inviting renovated colonial is the ideal spot for a peaceful is... Read More
June 2025
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1 2 3 4 5 6 $5600 7
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20 21 22 23 24 25 $6500 26
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BR 2 - Queen>Loft - King and two twins>Shared bath on main level
Oak Bluffs 847
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Oak Bluffs
$3,100.00 - $5,885.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 8 sleeps
Oak Bluffs 847
Welcome to this charming rental on Martha's Vineyard on Circuit Avenue in Oak Bluffs. This delightful apartment offers comfortable and spacious accomm... Read More
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BR1 Queen En Suite with Separate Shower Stall & Tub, First FloorBR2 Queen, Second FloorHall Bath with Tub Shower Combo, Second FloorBR3 Queen, Second FloorBR4 (2) Twin Beds & Bunk Bed, Second FloorHall Bath with Shower Stall, Second FloorBR5 (2) Bunk Beds & Trundle, Second FloorHall Bath with Shower Stall, First FloorLaundry Room, First Floor
Oak Bluffs 8091
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Oak Bluffs
$4,900.00 - $18,000.00 / per week
Beds 5 beds
Baths 4 Full Bath
Sleeps 15 sleeps
Oak Bluffs 8091
Two Week Minimum. Enjoy a relaxing stay in a charming, secluded, five-bedroom, eco-friendly home that sleeps up to 15, complete with total privacy, s... Read More
June 2025
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1 2 3 4 5 6 $4900 7
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