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52 properties available
This stunning custom 5-bedroom home is a true epitome of luxury, boasting extravagant furnishings, fine artwork, and cutting-edge technology. Equipped with gigabit-level internet, Apple televisions, and a SONOS sound system, you can enjoy streaming in the sunroom, kitchen, dining room, living room, library, lower-level game room, primary bedroom, a
$23,000.00 - $30,000.00 / per week + taxes and fees
5
beds
4
Full,
1
Half Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 14
This stunning custom 5-bedroom home is a true epitome of luxury, boasting extravagant furnishings, fine artwork, and cutting-edge technology. Equipped... Read More
This stunning custom 5-bedroom home is a true epitome of luxury, boasting extravagant furnishings, fine artwork, and cutting-edge technology. Equipped... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $27,500 6 | |
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July 2026
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August 2026
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Available
Unavailable
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This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New four bedroom custom home which overlooks the Vineyard Sound, offering breathtaking panoramic views to the Elizabeth Islands. With state of the art decor and interior furnishings, guests will enjoy environmentally sensiti
4
beds
3
Full,
1
Half Bath
sleeps
8
Pets Considered
No Events/Gatherings
Aquinnah 2501
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New four bedroom custom ... Read More
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New four bedroom custom ... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $35,000 6 | |
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| 21 | 22 | 23 | 24 | 25 | 26 | $35,000 27 |
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July 2026
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| 12 | 13 | 14 | 15 | 16 | 17 | $35,000 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $35,000 25 |
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $35,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $35,000 29 |
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Available
Unavailable
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Check-Out
Just a short distance down a charming up-island road, you will find this six bedroom estate, perfectly placed within it's surroundings, as if drawn on the page. A modern farmhouse with a sophisticated décor, a coalescence of mid-century modern, industrial and antique furnishings. Comfortable living spaces share a see-through gas fireplace, gourmet
$38,000.00 / per week + taxes and fees
6
beds
6
Full,
1
Half Bath
sleeps
12
Pets Considered
No Events/Gatherings
Chilmark 2010
Just a short distance down a charming up-island road, you will find this six bedroom estate, perfectly placed within it's surroundings, as if drawn o... Read More
Just a short distance down a charming up-island road, you will find this six bedroom estate, perfectly placed within it's surroundings, as if drawn o... Read More
June 2026
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July 2026
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August 2026
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Unavailable
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Martha's Vineyard gem. All you could want for Vineyard summer living. Beautifully appointed home with great indoor and outdoor spaces. This Down Harbor address offers an association beach and dock on beautiful Katama Bay, perfect for relaxing, sunning, swimming and fishing. In addition, the beach is ideal for launching a kayak or paddleboard and th
$35,000.00 / per week + taxes and fees
5
beds
5
Full,
2
Half Bath
sleeps
11
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 7180
Martha's Vineyard gem. All you could want for Vineyard summer living. Beautifully appointed home with great indoor and outdoor spaces. This Down Harbo... Read More
Martha's Vineyard gem. All you could want for Vineyard summer living. Beautifully appointed home with great indoor and outdoor spaces. This Down Harbo... Read More
June 2026
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July 2026
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| 12 | 13 | 14 | 15 | 16 | 17 | $35,000 18 |
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August 2026
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Available
Unavailable
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Step inside this stunning six-bedroom Katama retreat, where masterful design meets effortless comfort. The main house unfolds across multiple levels, blending open concept living with thoughtfully designed private spaces.
The upper level features an open kitchen, dining and living area, all of which open to outdoor spaces: a small deck with double
$35,000.00 - $40,000.00 / per week + taxes and fees
6
beds
8
Full,
2
Half Bath
sleeps
16
Pets Considered
Edgartown Katama 7179
Step inside this stunning six-bedroom Katama retreat, where masterful design meets effortless comfort. The main house unfolds across multiple levels, ... Read More
Step inside this stunning six-bedroom Katama retreat, where masterful design meets effortless comfort. The main house unfolds across multiple levels, ... Read More
June 2026
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July 2026
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August 2026
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Available
Unavailable
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Spectacular estate situated moments from the ocean and in the heart of downtown Edgartown with lush, flowering gardens. This spacious 4-bedroom custom home is the perfect vacation retreat. Designed by renowned architect Sam Sherman, it is luxuriously livable with four en suite bedrooms, a gourmet kitchen with marble countertops, a Viking stove, and
$12,500.00 - $35,000.00 / per week + taxes and fees
4
beds
4
Full,
1
Half Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 17
Spectacular estate situated moments from the ocean and in the heart of downtown Edgartown with lush, flowering gardens. This spacious 4-bedroom custom... Read More
Spectacular estate situated moments from the ocean and in the heart of downtown Edgartown with lush, flowering gardens. This spacious 4-bedroom custom... Read More
June 2026
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July 2026
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August 2026
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Available
Unavailable
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Stunning views over Eel Pond are perhaps the piece de resistance at this stunning in-town compound - bordered by the wildflowers of conservation land - the trails of Sheriff's Meadow are just one of the many afternoon adventures. Standing on the second floor deck and looking over the sprawling landscape, you truly feel on top of the world. The main
$40,000.00 - $48,750.00 / per week + taxes and fees
6
beds
7
Full,
1
Half Bath
sleeps
12
Pets Considered
No Events/Gatherings
Edgartown Downtown 71
Stunning views over Eel Pond are perhaps the piece de resistance at this stunning in-town compound - bordered by the wildflowers of conservation land ... Read More
Stunning views over Eel Pond are perhaps the piece de resistance at this stunning in-town compound - bordered by the wildflowers of conservation land ... Read More
June 2026
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July 2026
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August 2026
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Available
Unavailable
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Steeped in history, exuding luxury. The traditional whaling captain's home has been renovated to include seven bedrooms and seven and a half bathrooms over three buildings. Starting in the main house, you enter through perfectly replicated antique doors. On this level you will find a lovely sitting area that closes off for privacy and the first of
$35,000.00 - $75,000.00 / per week + taxes and fees
7
beds
7
Full,
1
Half Bath
sleeps
14
Pets Considered
No Events/Gatherings
Edgartown Downtown 25
Steeped in history, exuding luxury. The traditional whaling captain's home has been renovated to include seven bedrooms and seven and a half bathrooms... Read More
Steeped in history, exuding luxury. The traditional whaling captain's home has been renovated to include seven bedrooms and seven and a half bathrooms... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $65,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $65,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $65,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $65,000 27 |
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July 2026
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| 1 | 2 | 3 | $75,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $75,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $75,000 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $75,000 25 |
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August 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| $75,000 1 | ||||||
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| 9 | 10 | 11 | 12 | 13 | 14 | $75,000 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | $75,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $75,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
This elegant Village estate will transition you to island life the moment you enter the property. The perfect social house for you and your family to enjoy on Martha's Vineyard. Set back off the road providing quiet enjoyment and yet just minutes to Main Street and a few miles to South Beach. Beautiful and meticulously constructed, offering a sense
$25,000.00 - $35,000.00 / per week + taxes and fees
5
beds
5
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 35
This elegant Village estate will transition you to island life the moment you enter the property. The perfect social house for you and your family to ... Read More
This elegant Village estate will transition you to island life the moment you enter the property. The perfect social house for you and your family to ... Read More
June 2026
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July 2026
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August 2026
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Available
Unavailable
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This stunning walk to Edgartown home offers the best of both worlds: a serene private setting at the end of the cul-de-sac and prime access to Edgartown village. Just steps from a playground, pickleball courts, and a park, this home is designed for outdoor living! The spacious 600 square foot front porch, with its rocking chairs, swing and dining t
$10,000.00 - $29,500.00 / per week + taxes and fees
4
beds
3
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 150
This stunning walk to Edgartown home offers the best of both worlds: a serene private setting at the end of the cul-de-sac and prime access to Edgarto... Read More
This stunning walk to Edgartown home offers the best of both worlds: a serene private setting at the end of the cul-de-sac and prime access to Edgarto... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $10,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $18,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $29,500 20 |
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July 2026
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $29,500 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $12,000 29 |
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Available
Unavailable
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Check-Out
As you head out of town down a private dirt road lined with glimpses of the ocean and sprawling lawns, you round a corner and find a house where the ocean envelopes you. The view from the driveway looks out to the front lawn, porch, patio, pool and ocean. A well-thought out design with an emphasis on private spaces, multiple living spaces both ind
$35,000.00 - $60,000.00 / per week + taxes and fees
7
beds
6
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 109
As you head out of town down a private dirt road lined with glimpses of the ocean and sprawling lawns, you round a corner and find a house where the o... Read More
As you head out of town down a private dirt road lined with glimpses of the ocean and sprawling lawns, you round a corner and find a house where the o... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $37,500 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $37,500 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $37,500 20 |
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July 2026
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August 2026
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Available
Unavailable
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The Preserve, located off County Road, offers luxurious accommodations with five modern, air-conditioned bedrooms, each equipped with an en-suite bathroom. The first-floor king suite features a spacious en-suite bathroom complete with a soaking tub and a separate shower. On the second floor, you will find four additional en-suite bedrooms along wit
$16,000.00 - $33,000.00 / per week + taxes and fees
5
beds
5
Full,
1
Half Bath
sleeps
10
Pets Considered
No Events/Gatherings
Oak Bluffs 826
The Preserve, located off County Road, offers luxurious accommodations with five modern, air-conditioned bedrooms, each equipped with an en-suite bath... Read More
The Preserve, located off County Road, offers luxurious accommodations with five modern, air-conditioned bedrooms, each equipped with an en-suite bath... Read More
June 2026
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|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $16,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $16,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $20,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $20,000 27 |
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July 2026
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| 1 | 2 | 3 | $30,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $30,000 11 |
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August 2026
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Available
Unavailable
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