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 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorBR2 Queen, 2nd floorBR3 Queen, 2nd floorHall bath with tub/shower, 2nd floor
Oak Bluffs 8105
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Oak Bluffs
$4,200.00 - $7,400.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (2)
Oak Bluffs 8105
This wonderful three bedroom Cape is located in a quiet neighborhood in the development of Deer Run just off of Barnes Road in Oak Bluffs. There is so... Read More
June 2025
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1 2 3 4 5 6 $5600 7
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17 18 19 20 21 22 $7400 23
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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 8139
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Oak Bluffs Pet Friendly
$3,500.00 - $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 Queen, First FloorHall Bath with Tub Shower Combo, First FloorBR2 Queen, Second FloorHall Bath with Tub Shower Combo, Second FloorBR3 Double, Second Floor
Hot HOT 19
Oak Bluffs 8000
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Oak Bluffs Pet Friendly
$3,500.00 - $6,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 5 sleeps
Oak Bluffs 8000
This three-bedroom home in downtown Oak Bluffs has been beautifully restored, preserving its historic character while adding modern comforts. Inside, ... Read More
June 2025
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15 16 17 18 19 20 $3500 21
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    1 2 3 4 $5000 5
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BR1 Queen En Suite with Shower Stall, First FloorBR2 Queen En Suite with Shower Stall, Second FloorBR3 Queen, Second FloorHall Bath with Shower Tub Combo, Second FloorBR4 (2) Twin Beds, Second FloorHall Bath with Tub and Handheld Shower, First FloorPowder Room, Lower LevelGuest House:BR5 Queen En Suite with Shower Tub Combo, First Floor
Oak Bluffs 8172
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Oak Bluffs
$4,300.00 - $7,300.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Rating 5 (1)
Oak Bluffs 8172
Beautifully appointed custom five bedroom gingerbread main and guest house in the heart of Oak Bluffs awaits your summer vacation. It has been updated... Read More
June 2025
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8 9 10 11 12 13 $5300 14
15 16 17 18 19 20 $7300 21
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BR1 King en suite with shower stall, 1st floorBR2 Queen, 1st floorBR3 Double, 1st floor BR4 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorDouble sofa bed, 1st floor sitting roomHalf bath, 2nd floor
Hot HOT 248
Oak Bluffs 8120
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Oak Bluffs
$5,500.00 - $12,500.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 4.6 (3)
Oak Bluffs 8120
Historic Cape reverse set up, with living area, kitchen and powder room on the upper level with spectacular ocean views and the remaining living space... Read More
June 2025
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1 2 3 4 5 6 $6000 7
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BR1 King en suite with tub and shower, 1st floorBR2 Queen with hall bath, 1st floorBR3 (2) Twins, (1) set of Twin bunks with hall bath, 1st floor
Hot HOT 10
Oak Bluffs 8032
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Oak Bluffs Pet Friendly
$7,000.00 - $12,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 8032
Dramatic views! Enjoy the perfect vacation spot for all families. Located on the lagoon side of Barnes road, this 3 bedroom home includes a small beac... 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 $10000 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 8814
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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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15 16 17 18 19 20 $18825 21
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    1 2 3 4 $18825 5
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BR1 Queen, 1st floorBR2 King, 2nd floorBR3 Queen, 2nd floorBR4 (2)Twin beds, 2nd floor
Oak Bluffs 8173
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Oak Bluffs
$3,000.00 - $8,000.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8173
Start your Vineyard memories in this home outfitted perfectly for your Vineyard vacation! Decorated in a casually elegant fashion with a nod to our na... Read More
June 2025
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1 2 3 4 5 6 $4000 7
8 9 10 11 12 13 $4000 14
15 16 17 18 19 20 $5000 21
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BR1 King, Second FloorHall Bath, First FloorOverflow: Queen, Second Floor
Oak Bluffs 848
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Oak Bluffs
$3,000.00 - $5,000.00 / per week
Beds 1 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 848
Welcome to this charming cottage nestled in the heart of Oak Bluffs, within the MV Camp Meeting Association, famously known as the "Campgrounds." This... Read More
June 2025
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1 2 3 4 5 6 $3000 7
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    1 2 3 4 $3500 5
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17 18 19 20 21 22 $5000 23
24 25 26 27 28 29 $3000 30
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BR1 King with Laundry, Hall Bath. Pair of Queen Beds in Loft Over Living Room
Oak Bluffs 874
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Oak Bluffs
$1,800.00 - $3,750.00 / per week
Beds 1 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Rating 5 (1)
Oak Bluffs 874
A stunning, newly renovated condo on Ocean Park - pristine finishes and a modern floorplan with an open concept kitchen, dining, and living area, stai... Read More
June 2025
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1 2 3 4 5 6 $2500 7
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13 14 15 16 17 18 $3750 19
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17 18 19 20 21 22 $3750 23
24 25 26 27 28 29 $2700 30
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BR1 Queen, Second FloorBR2 Queen, Second FloorBR3 (5) Twin Beds, Second FloorHall Bath with Shower Tub Combo, Second FloorHall Bath with Shower Stall, First Floor
Hot HOT 12
Oak Bluffs 8065
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Oak Bluffs
$7,500.00 - $10,500.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 9 sleeps
Oak Bluffs 8065
By the sea, by the sea! Picture yourself on the deck of this wonderful East Chop home with private beach, sweeping views of Vineyard Sound, huge flat ... Read More
June 2025
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1 2 3 4 5 6 $7500 7
8 9 10 11 12 13 $7500 14
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10 11 12 13 14 15 $8500 16
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BR1 King en suite, 1st floorBR2 Queen en suite, 2nd floorBR3 (2)Twin beds, 2nd floorHall bath of tub shower combo, 2nd floor
Oak Bluffs 814
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Oak Bluffs
$5,000.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 4 (1)
Oak Bluffs 814
Lovely Oak Bluffs home in a private location with association access to Sengekontacket Pond. Just a street over from Farm Neck Golf and Tennis. Minu... Read More
June 2025
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1 2 3 4 5 6 $5000 7
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    1 2 3 4 $5000 5
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