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Properties Available 647 properties available
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
$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 2026
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This spacious five bedroom home has sparkling reviews when it comes to fresh, clean and lovely decor throughout. Inside you will find a spacious first floor living space equipped with a well stocked kitchen, open dining and living area as you enjoy the tranquil view of the lovely landscaped yard and an adorable and quaint screened porch off the kit
$3,000.00 - $7,750.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 781
This spacious five bedroom home has sparkling reviews when it comes to fresh, clean and lovely decor throughout. Inside you will find a spacious first... Read More
June 2026
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Gracious and spacious, this 4-bedroom, 3-bath home on two lush acres in Katama and is minutes from South Beach. The open floorplan lends itself to a relaxing vacation, complete with stunning views of the rolling fields of the Farm Institute and beyond. The fully-equipped gourmet kitchen has a large center island with seating for six, and two dish
Hot HOT 11
$8,200.00 - $12,900.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full Bath
Sleeps sleeps 10
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Katama 553
Gracious and spacious, this 4-bedroom, 3-bath home on two lush acres in Katama and is minutes from South Beach. The open floorplan lends itself to a ... Read More
June 2026
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  1 2 3 4 5 $8,200 6
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Let this four bedroom, three bath home eases you into a state of relaxation and rejuvenation for your upcoming Vineyard escape. Boasting accommodations for ten guests in this coastal themed décor, you will find it well equipped with an added enjoyment of a heated pool. The first floor has an open kitchen and dining room area that flows to the outs
$4,500.00 - $9,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full Bath
Sleeps sleeps 10
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown 715
Let this four bedroom, three bath home eases you into a state of relaxation and rejuvenation for your upcoming Vineyard escape. Boasting accommodation... Read More
June 2026
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Classic East Chop Victorian with all of the amenities that they didn't have back then! While away a summer afternoon sitting on the porch watching the boats go by and taking in the sea breeze! The porch is a showstopper, but step inside and let the vacation begin! Tastefully decorated to create a casual vibe: the kitchen is dressed with granite cou
$13,500.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 818
Classic East Chop Victorian with all of the amenities that they didn't have back then! While away a summer afternoon sitting on the porch watching the... Read More
June 2026
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A beautiful compound on South Water Street, perfect for a summer vacation! Featuring a two-bedroom Main house with wraparound porch and shared yard leading to the three-bedroom guesthouse, offering an abundance of room for everyone both inside and out! The beautiful Main house has a large fireplace and double-height ceilings, an open living, dining
$5,000.00 - $10,000.00 / per week + taxes and fees
Beds 5 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 299
A beautiful compound on South Water Street, perfect for a summer vacation! Featuring a two-bedroom Main house with wraparound porch and shared yard le... Read More
June 2026
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Discover tranquility in this ideally situated main and guest residence, just a mile from the village and two miles from South Beach. The main house features an inviting floor plan that seamlessly connects to a deck overlooking the yard and pool. On the first level, you'll find a spacious primary suite and a small deck, perfect for savoring your mor
$5,900.00 - $19,500.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 2 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 525
Discover tranquility in this ideally situated main and guest residence, just a mile from the village and two miles from South Beach. The main house fe... Read More
June 2026
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Welcome to your vacation getaway, where relaxation and privacy combine in this stunning 3-bedroom, 3.5-bathroom property. Nestled in a peaceful neighborhood, only a mile from South Beach, this home boasts a spacious open concept living space, perfect for entertaining with family and friends. Inside you'll be greeted by an abundance of natural ligh
$7,500.00 - $11,500.00 / per week + taxes and fees
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 7164
Welcome to your vacation getaway, where relaxation and privacy combine in this stunning 3-bedroom, 3.5-bathroom property. Nestled in a peaceful neighb... Read More
June 2026
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Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hill location. Enjoy breathtaking water views from nearly every room and an ideal layout designed for both comfort and connection. The main level features an open-concept kitchen, dining, and living are
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July 3rd - July 11th, July 11th - July 18th, July 18th - July 25th, July 25th - August 1st
$10,500.00 - $18,000.00 / per week + taxes and fees
Beds 5 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Chilmark 2050
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hi... Read More
June 2026
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This gracious home, beautifully restored reflects a combination of original and new - with an abundance of outdoor space to run about! The woodwork exudes a sense of warmth, and the sunlight pours through the windows of both bedrooms. Featuring two bedrooms and one bath, all uniform on one level, it is just enough space to feel at home. A lovely t
$4,900.00 - $5,900.00 / per week + taxes and fees
Beds 2 beds
Baths 1 Full Bath
Sleeps sleeps 4
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Vineyard Haven 929
This gracious home, beautifully restored reflects a combination of original and new - with an abundance of outdoor space to run about! The woodwork e... Read More
June 2026
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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 yard and sunsets. The house has large eat-in kitchen, great living/dining room. Families, girlfriend weekends, Derby fishermen. A comfortable seaside home with privacy, yet convenient to Oak Bluffs an
$7,500.00 - $10,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 9
Not Pet Friendly Pets Not Allowed
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 2026
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This classic colonial home in Oak Bluffs offers the perfect Martha's Vineyard getaway for families and small groups. With five comfortable bedrooms accommodating up to eight guests, the home blends timeless charm with relaxed coastal living. Inside, you'll find inviting, well-appointed bedrooms designed for restful nights after a day of island expl
Hot HOT 28
$5,000.00 - $10,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 8123
This classic colonial home in Oak Bluffs offers the perfect Martha's Vineyard getaway for families and small groups. With five comfortable bedrooms ac... Read More
June 2026
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