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Properties Available 627 properties available
This five bedroom home is truly a quintessential Chappy retreat. Set in the woods, this property offers privacy and a beautiful distant view of Edgartown Harbor down a long and sloping lawn. With its large outdoor deck and inviting wide open interior, this home provides a wonderful space to explore, relax, and entertain both inside and out. An inte
Edgartown Chappaquiddick 387
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$8,150.00 / per week + taxes and fees
Beds 3 beds
Baths 3 Full Bath
Sleeps sleeps 9
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Chappaquiddick 387
This five bedroom home is truly a quintessential Chappy retreat. Set in the woods, this property offers privacy and a beautiful distant view of Edgart... Read More
June 2027
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    1 2 3 4 $8,150 5
6 7 8 9 10 11 $8,150 12
13 14 15 16 17 18 $8,150 19
20 21 22 23 24 25 $8,150 26
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July 2027
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August 2027
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15 16 17 18 19 20 $8,150 21
22 23 24 25 26 27 $8,150 28
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Stunning Chappaquiddick four bedroom home with water views. Spacious open living and kitchen area. Dining room features an open cathedral ceiling to the second floor with interior balcony. Beautifully designed to capture the feel of both Chappaquiddick and modern living. Water views abound from primary bedroom and both upper and lower screened p
Edgartown Chappaquiddick 364
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$6,000.00 - $8,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full, 2 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Chappaquiddick 364
Stunning Chappaquiddick four bedroom home with water views. Spacious open living and kitchen area. Dining room features an open cathedral ceiling to... Read More
June 2027
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    1 2 3 4 $6,000 5
6 7 8 9 10 11 $6,000 12
13 14 15 16 17 18 $6,000 19
20 21 22 23 24 25 $7,000 26
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July 2027
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25 26 27 28 29 30 $8,000 31
August 2027
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1 2 3 4 5 6 $8,000 7
8 9 10 11 12 13 $8,000 14
15 16 17 18 19 20 $8,000 21
22 23 24 25 26 27 $6,000 28
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Sengekontacket Association offers a charming residential community with convenient access to tennis courts and a picturesque pond, all just a short distance from town. This beautifully renovated town-house style condo exudes a sense of newness, resembling a luxury residence in its ambiance. It boasts tasteful decor and comes fully equipped with all
Hot HOT 28
Oak Bluffs Condo 8015
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$4,000.00 - $5,500.00 / per week + taxes and fees
Beds 2 beds
Baths 2 Full Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs Condo 8015
Sengekontacket Association offers a charming residential community with convenient access to tennis courts and a picturesque pond, all just a short di... Read More
June 2027
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    1 2 3 4 $4,500 5
6 7 8 9 10 11 $4,500 12
13 14 15 16 17 18 $5,500 19
20 21 22 23 24 25 $5,500 26
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July 2027
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25 26 27 28 29 30 $5,500 31
August 2027
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1 2 3 4 5 6 $5,500 7
8 9 10 11 12 13 $5,500 14
15 16 17 18 19 20 $5,500 21
22 23 24 25 26 27 $5,500 28
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Welcome to our exquisite vacation home in Katama! This contemporary home boasts 4 bedrooms, 2.5 baths, and sweeping views of the plains of Katama, and the distant ocean. Step onto the luxurious hardwood deck and indulge in the breathtaking scenery that surrounds you. The highlight of the property is the inviting pool area, perfect for relaxing and
Edgartown Katama 5011
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$7,400.00 - $22,700.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Edgartown Katama 5011
Welcome to our exquisite vacation home in Katama! This contemporary home boasts 4 bedrooms, 2.5 baths, and sweeping views of the plains of Katama, and... Read More
June 2027
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    1 2 3 4 $13,700 5
6 7 8 9 10 11 $13,700 12
13 14 15 16 17 18 $13,700 19
20 21 22 23 24 25 $19,100 26
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July 2027
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        1 2 $19,100 3
4 5 6 7 8 9 $19,100 10
11 12 13 14 15 16 $19,100 17
18 19 20 21 22 23 $19,100 24
25 26 27 28 29 30 $22,700 31
August 2027
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1 2 3 4 5 6 $22,700 7
8 9 10 11 12 13 $22,700 14
15 16 17 18 19 20 $22,700 21
22 23 24 25 26 27 $22,700 28
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One-bedroom guest house in Katama. First floor hosts an open floor plan with a newly furnished kitchen, bar seating, and a bright and airy living area. Upstairs you'll find a home office space with a second sitting area for lounging. The second floor also features a queen-size bedroom, with plenty of natural lighting and full bath with a spacious,
Edgartown Katama 504
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$2,000.00 - $3,250.00 / per week + taxes and fees
Beds 1 beds
Baths 1 Full Bath
Sleeps sleeps 2
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 504
One-bedroom guest house in Katama. First floor hosts an open floor plan with a newly furnished kitchen, bar seating, and a bright and airy living area... Read More
June 2027
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    1 2 3 4 $2,250 5
6 7 8 9 10 11 $2,250 12
13 14 15 16 17 18 $2,250 19
20 21 22 23 24 25 $3,000 26
27 28 29 30      
July 2027
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11 12 13 14 15 16 $3,000 17
18 19 20 21 22 23 $3,250 24
25 26 27 28 29 30 $3,250 31
August 2027
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1 2 3 4 5 6 $3,250 7
8 9 10 11 12 13 $3,250 14
15 16 17 18 19 20 $3,000 21
22 23 24 25 26 27 $2,000 28
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A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across from Ocean Park. The best spot for the annual Oak Bluffs Fireworks and Grand Illumination, outfitted with all of the modern amenities you could need. There are two living areas, both on the first flo
Hot HOT 50
Oak Bluffs 825
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$9,900.00 - $20,900.00 / per week + taxes and fees
Beds 6 beds
Baths 3 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 825
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across f... Read More
June 2027
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    1 2 3 4 $11,900 5
6 7 8 9 10 11 $11,900 12
13 14 15 16 17 18 $12,900 19
20 21 22 23 24 25 $15,900 26
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July 2027
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        1 2 $16,900 3
4 5 6 7 8 9 $16,900 10
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18 19 20 21 22 23 $17,900 24
25 26 27 28 29 30 $20,900 31
August 2027
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1 2 3 4 5 6 $20,900 7
8 9 10 11 12 13 $20,900 14
15 16 17 18 19 20 $20,900 21
22 23 24 25 26 27 $15,900 28
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Experience the epitome of luxury at this estate in the heart of Katama's most sought-after enclave, where over 6,700 square feet of impeccably curated living space invite you to indulge in a lifestyle reminiscent of a five-star retreat. This five-bedroom residence seamlessly blends timeless elegance with contemporary comfort. The interiors are all
Edgartown Katama 673
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$25,000.00 - $50,000.00 / per week + taxes and fees
Beds 5 beds
Baths 6 Full, 2 Half Bath
Sleeps sleeps 10
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Katama 673
Experience the epitome of luxury at this estate in the heart of Katama's most sought-after enclave, where over 6,700 square feet of impeccably curated... Read More
June 2027
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    1 2 3 4 $35,000 5
6 7 8 9 10 11 $35,000 12
13 14 15 16 17 18 $35,000 19
20 21 22 23 24 25 $50,000 26
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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 much to do at this property; relax on the back deck, enjoy morning coffee on the front farmers porch, play afternoon yard games, or just grill and dine outdoors. One bedroom on the first floor with t
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Oak Bluffs 8105
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$4,200.00 - $7,700.00 / 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
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 2027
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    1 2 3 4 $5,600 5
6 7 8 9 10 11 $5,600 12
13 14 15 16 17 18 $5,600 19
20 21 22 23 24 25 $6,800 26
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July 2027
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        1 2 $7,140 3
4 5 6 7 8 9 $7,140 10
11 12 13 14 15 16 $7,140 17
18 19 20 21 22 23 $7,140 24
25 26 27 28 29 30 $7,700 31
August 2027
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1 2 3 4 5 6 $7,700 7
8 9 10 11 12 13 $7,700 14
15 16 17 18 19 20 $7,700 21
22 23 24 25 26 27 $5,600 28
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Discover "Waters End," a charming vacation property located at the end of South Water Street in Edgartown, Martha's Vineyard. This spacious five-bedroom traditional-style home offers a convenient location within a short distance to downtown and features a bike path that leads to the beach. The property includes a beautifully landscaped yard that i
Hot HOT 21
Edgartown Downtown 124
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$4,000.00 - $6,950.00 / per week + taxes and fees
Beds 5 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 124
Discover "Waters End," a charming vacation property located at the end of South Water Street in Edgartown, Martha's Vineyard. This spacious five-bedro... Read More
June 2027
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    1 2 3 4 $4,850 5
6 7 8 9 10 11 $4,850 12
13 14 15 16 17 18 $6,950 19
20 21 22 23 24 25 $6,950 26
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25 26 27 28 29 30 $6,950 31
August 2027
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Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhouse offers a spacious first-floor living area. The large chef's kitchen features a prep island, granite countertops, Le Creuset cookware, a wine fridge, two dishwashers, and commercial-grade stainless s
Edgartown Katama 522
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$14,000.00 - $35,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 522
Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhous... Read More
June 2027
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Let the vacation begin! In Edgartown, equal distance from South Beach and State beach and a very central location. The traditional cape style home has space to spread out. The downstairs is an open floor plan with a large dining area and living area. Through the dining area you will find a comfortable family room complete with a large TV. Above the
Edgartown 747
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$3,000.00 - $6,800.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full Bath
Sleeps sleeps 10
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown 747
Let the vacation begin! In Edgartown, equal distance from South Beach and State beach and a very central location. The traditional cape style home has... Read More
June 2027
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    1 2 3 4 $3,000 5
6 7 8 9 10 11 $3,000 12
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18 19 20 21 22 23 $5,500 24
25 26 27 28 29 30 $6,800 31
August 2027
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15 16 17 18 19 20 $5,500 21
22 23 24 25 26 27 $5,500 28
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"Beach Rose" is a bright and airy two bedroom home. With a large fully equipped kitchen, dining area, and living room, it is your home on the Vineyard. Skylights and solarium style windows bring natural light throughout the home. One bedroom and one bath are located on the main level with the second bedroom and second bath located on the upper leve
Edgartown 7815
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$2,000.00 - $4,100.00 / per week + taxes and fees
Beds 2 beds
Baths 2 Full Bath
Sleeps sleeps 4
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 7815
"Beach Rose" is a bright and airy two bedroom home. With a large fully equipped kitchen, dining area, and living room, it is your home on the Vineyard... Read More
June 2027
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    1 2 3 4 $2,800 5
6 7 8 9 10 11 $2,800 12
13 14 15 16 17 18 $3,200 19
20 21 22 23 24 25 $4,100 26
27 28 29 30      
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        1 2 $4,100 3
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18 19 20 21 22 23 $4,100 24
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15 16 17 18 19 20 $4,100 21
22 23 24 25 26 27 $3,200 28
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