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Properties Available 642 properties available
This tastefully decorated, centrally air conditioned, four bedroom, two and one half bathroom home is nestled in the Dodgers Hole neighborhood on a quiet street with a large yard, back deck and plenty of off street parking. It offers a grand kitchen with granite countertops and stainless steel appliances. The dining area can accommodate ten. This a
Edgartown 7783
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$4,500.00 - $5,500.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 7783
This tastefully decorated, centrally air conditioned, four bedroom, two and one half bathroom home is nestled in the Dodgers Hole neighborhood on a qu... Read More
August 2026
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September 2026
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    1 2 3 4 $4,700 5
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13 14 15 16 17 18 $4,500 19
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Off of Metcalf Road to Saddle Club is this charming three-bedroom summer rental just waiting for you to enjoy it. Inside you will find a well-equipped kitchen open to the dining area and Cathedral-ceiling living area beyond. Rounding out the first floor are two of the three bedrooms and a hall bath. Up the stairs is the primary bedroom with adjoi
Edgartown 711
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$2,650.00 - $3,750.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 711
Off of Metcalf Road to Saddle Club is this charming three-bedroom summer rental just waiting for you to enjoy it. Inside you will find a well-equippe... Read More
August 2026
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September 2026
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    1 2 3 4 $3,000 5
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13 14 15 16 17 18 $3,000 19
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October 2026
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Stately Katama home with everything you need for a perfect summer vacation! The open floor plan is perfect for gathering and entertaining with a well equipped kitchen, an eat in kitchen and dining room. Decorated with a nautical flair, evoking a relaxed feeling, the bedrooms are roomy and each has their own bathrooms including the primary with a sp
Edgartown Katama 603
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$12,500.00 - $15,500.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 603
Stately Katama home with everything you need for a perfect summer vacation! The open floor plan is perfect for gathering and entertaining with a well ... Read More
August 2026
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16 17 18 19 20 21 $15,500 22
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September 2026
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    1 2 3 4 $15,000 5
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October 2026
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        1 2 $15,000 3
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A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews from the living, kitchen and dining areas, opening to a large outdoor deck. There is an ensuite bedroom on the main level and three additional bedrooms on the lower level as well as a media room with 6
Oak Bluffs 8104
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$4,900.00 - $15,900.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 8104
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
August 2026
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6 7 8 9 10 11 $4,900 12
13 14 15 16 17 18 $6,500 19
20 21 22 23 24 25 $6,000 26
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October 2026
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        1 2 $7,000 3
4 5 6 7 8 9 $6,000 10
11 12 13 14 15 16 $6,000 17
18 19 20 21 22 23 $6,000 24
25 26 27 28 29 30 $6,000 31
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This exceptional house is the perfect location for all your Vineyard adventures. Just a stone's throw from Main Street in Edgartown, you can easily explore the shops, galleries, and amazing restaurants or soak up the stunning Edgartown harbor. Pedal your bike to South Beach, less than three miles away, or State Beach, a little under two miles away.
Hot HOT 12
Edgartown Downtown 132
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$7,000.00 - $16,500.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 132
This exceptional house is the perfect location for all your Vineyard adventures. Just a stone's throw from Main Street in Edgartown, you can easily ex... Read More
August 2026
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16 17 18 19 20 21 $12,500 22
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September 2026
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    1 2 3 4 5
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13 14 15 16 17 18 $9,500 19
20 21 22 23 24 25 $7,000 26
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18 19 20 21 22 23 $7,000 24
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This classic waterfront home just had an all-encompassing renovation by one of the Vineyard's most respected builders and talented design team - pairing the mesmerizing views of Katama Bay with a California chic decor - natural fibers and textures, crisp, calming palette with an elevated and relaxed feel throughout. Renovations include an open-con
Edgartown Katama 598
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$7,000.00 - $20,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 598
This classic waterfront home just had an all-encompassing renovation by one of the Vineyard's most respected builders and talented design team - pairi... Read More
August 2026
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    1 2 3 4 $17,500 5
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Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architecturally designed with two primary suites, a chef's Kitchen, open and sprawling dining and living spaces all on the main level with peaceful water views of Farm Pond and a distance view of the Atlantic
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Oak Bluffs 807
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$9,500.00 - $23,500.00 / per week + taxes and fees
Beds 6 beds
Baths 5 Full, 2 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 807
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architect... Read More
August 2026
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Edgartown vacation home offering great privacy, lots of light, and open contemporary design. Spend days at the beach or wandering around town to peruse the many shops, restaurants, galleries and return home to relax and enjoy the tranquility of this quiet, settled Edgartown neighborhood. Preparing meals for family and friends couldn't be easier in
Edgartown 705
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$3,000.00 - $4,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 705
Edgartown vacation home offering great privacy, lots of light, and open contemporary design. Spend days at the beach or wandering around town to peru... Read More
August 2026
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This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall bathroom. The second floor boasts a spacious king suite complete with a private bath. Both the king bedroom and the living area are equipped with AC mini-split units for added comfort. The cottage is l
Edgartown Chappaquiddick 407
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$3,000.00 - $4,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Chappaquiddick 407
This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall b... Read More
August 2026
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        1 2 $3,500 3
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DEXTER HOUSE - Part of a two house waterfront complex overlooking the harbor with spectacular views of Chappaquiddick and the Vineyard Sound. The living room is open to the dining area and chef's kitchen, with French doors that opens out to the second level deck with water views in all directions. State of the art electronics, digital satellite and
Edgartown Downtown 285
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$7,500.00 - $25,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full Bath
Sleeps sleeps 8
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 285
DEXTER HOUSE - Part of a two house waterfront complex overlooking the harbor with spectacular views of Chappaquiddick and the Vineyard Sound. The livi... Read More
August 2026
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18 19 20 21 22 23 $10,000 24
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Experience the charm of this inviting single-story rental home, the perfect retreat for your next vacation. Thoughtfully furnished with brand-new décor and modernized bathrooms, this cozy getaway ensures a comfortable and relaxing stay. The finished basement offers an additional TV room and games for extra entertainment. Unwind on the welcoming bac
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Oak Bluffs 8161
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$3,950.00 - $5,000.00 / per week + taxes and fees
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps sleeps 6
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Oak Bluffs 8161
Experience the charm of this inviting single-story rental home, the perfect retreat for your next vacation. Thoughtfully furnished with brand-new déco... Read More
August 2026
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Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of the property lies an impressive 140-foot deep-water dock, complemented by a stunning five-bedroom main house and a charming three-bedroom guesthouse, making it an ideal venue for both leisure and ent
Edgartown Chappaquiddick 337
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$20,000.00 - $30,000.00 / per week + taxes and fees
Beds 8 beds
Baths 6 Full, 1 Half Bath
Sleeps sleeps 16
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Chappaquiddick 337
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of... Read More
August 2026
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    1 2 3 4 $25,000 5
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        1 2 $25,000 3
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