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52 properties available
Waterfront West Chop property overlooking Vineyard Sound. This expansive single-story home with separate second-floor apartment and short path to private beach, has plenty of room for everyone. Begin the day in the well appropriate kitchen, eat in the breakfast nook or the nearby screened in porch, both facing the water. Through the butler's pant
$17,500.00 - $28,000.00 / per week + taxes and fees
6
beds
5
Full Bath
sleeps
12
Pets Considered
No Events/Gatherings
Vineyard Haven 910
Waterfront West Chop property overlooking Vineyard Sound. This expansive single-story home with separate second-floor apartment and short path to pri... Read More
Waterfront West Chop property overlooking Vineyard Sound. This expansive single-story home with separate second-floor apartment and short path to pri... Read More
August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $28,000 29 |
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September 2026
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October 2026
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Available
Unavailable
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European elegance combines with a casual, nautical charm to create a style which is both welcoming and glamorous in this seven-bedroom, six and-a-half bath estate. A perfectly appointed kitchen and butlers pantry accommodate both formal dinner parties and cozy meals on the cushioned window seat of the breakfast nook - perhaps read the paper on the
$29,500.00 / per week + taxes and fees
7
beds
6
Full,
1
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 125
European elegance combines with a casual, nautical charm to create a style which is both welcoming and glamorous in this seven-bedroom, six and-a-half... Read More
European elegance combines with a casual, nautical charm to create a style which is both welcoming and glamorous in this seven-bedroom, six and-a-half... Read More
August 2026
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September 2026
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| 1 | 2 | 3 | 4 | $29,500 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | $29,500 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | $29,500 19 |
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October 2026
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| 1 | 2 | $29,500 3 | ||||
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| 11 | 12 | 13 | 14 | 15 | 16 | $29,500 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $29,500 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $29,500 31 |
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
August 2026
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September 2026
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October 2026
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Available
Unavailable
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This magnificent home seamlessly combines opulence and grandeur, a departure from the typical beach house aesthetic. High ceilings, luxurious fabrics, and elegant hardware are harmoniously blended in soothing shades of blue, natural wood floors, and white stone countertops. The expansive layout boasts multiple living spaces, including a grand livin
$21,000.00 - $35,000.00 / per week + taxes and fees
4
beds
4
Full,
2
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 527
This magnificent home seamlessly combines opulence and grandeur, a departure from the typical beach house aesthetic. High ceilings, luxurious fabrics,... Read More
This magnificent home seamlessly combines opulence and grandeur, a departure from the typical beach house aesthetic. High ceilings, luxurious fabrics,... Read More
August 2026
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September 2026
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| 6 | 7 | 8 | 9 | 10 | 11 | $21,000 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | $21,000 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | $21,000 26 |
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October 2026
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| 1 | 2 | $21,000 3 | ||||
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| 18 | 19 | 20 | 21 | 22 | 23 | $21,000 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $21,000 31 |
Available
Unavailable
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A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and five minutes to Main Street, and all of the best shops and restaurants. Offering five ensuite bedrooms, including a private bedroom and bath in the carriage house, the main house features a large gre
$22,500.00 - $35,000.00 / per week + taxes and fees
5
beds
6
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 173
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and... Read More
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and... Read More
August 2026
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September 2026
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October 2026
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Available
Unavailable
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This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The main house includes six bedrooms, along with two separate guest quarters. One guest section is located on the first floor, offering two bedrooms, two full bathrooms, and air conditioning throughout. The second guest unit is on the second floor, provid
$15,000.00 - $39,000.00 / per week + taxes and fees
9
beds
9
Full,
1
Half Bath
sleeps
18
Pets Not Allowed
No Events/Gatherings
Oak Bluffs 8148
This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The main house includes six bedrooms, along with two se... Read More
This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The main house includes six bedrooms, along with two se... Read More
August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $25,000 22 |
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September 2026
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October 2026
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| 4 | 5 | 6 | 7 | 8 | 9 | $15,000 10 |
| 11 | 12 | 13 | 14 | 15 | 16 | $15,000 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $15,000 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $15,000 31 |
Available
Unavailable
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Check-Out
Edgartown 7747
... Read More
... Read More
August 2026
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September 2026
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| 1 | 2 | 3 | 4 | $20,000 5 | ||
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October 2026
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Available
Unavailable
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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
August 2026
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September 2026
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| 13 | 14 | 15 | 16 | 17 | 18 | $23,000 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | $23,000 26 |
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October 2026
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| 1 | 2 | $23,000 3 | ||||
| 4 | 5 | 6 | 7 | 8 | 9 | $23,000 10 |
| 11 | 12 | 13 | 14 | 15 | 16 | $23,000 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $23,000 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $23,000 31 |
Available
Unavailable
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With the open, airy sophistication of a city loft, this house offers beautiful views overlooking conservation land and peeks of Cape Pogue and the outer harbor. The first floor features an open kitchen with state of the art appliances, a large center island, flowing into dining and an open living area with double-height ceilings, luxurious furnishi
$7,500.00 - $28,500.00 / per week + taxes and fees
6
beds
4
Full,
1
Half Bath
sleeps
12
Pets Considered
No Events/Gatherings
Edgartown Downtown 74
With the open, airy sophistication of a city loft, this house offers beautiful views overlooking conservation land and peeks of Cape Pogue and the out... Read More
With the open, airy sophistication of a city loft, this house offers beautiful views overlooking conservation land and peeks of Cape Pogue and the out... Read More
August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $25,500 29 |
| 30 | 31 |
September 2026
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| 1 | 2 | 3 | 4 | $19,500 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | $18,000 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | $17,500 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | $17,500 26 |
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October 2026
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| 1 | 2 | $14,000 3 | ||||
| 4 | 5 | 6 | 7 | 8 | 9 | $14,000 10 |
| 11 | 12 | 13 | 14 | 15 | 16 | $12,500 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $7,500 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $7,500 31 |
Available
Unavailable
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Nestled amongst rolling spring lawns in a quiet, up-island setting sits a haven, echoing clean lines, meticulous design and comfort. This five bedroom with two en suite primarys, provides an abundance of sleeping room, with plenty of living spaces for family and friends to spread out. This home features a large kitchen with plenty of counter space
$19,500.00 - $30,000.00 / per week + taxes and fees
5
beds
4
Full,
2
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
West Tisbury 100028
Nestled amongst rolling spring lawns in a quiet, up-island setting sits a haven, echoing clean lines, meticulous design and comfort. This five bedroom... Read More
Nestled amongst rolling spring lawns in a quiet, up-island setting sits a haven, echoing clean lines, meticulous design and comfort. This five bedroom... Read More
August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $26,000 29 |
| 30 | 31 |
September 2026
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| 1 | 2 | 3 | 4 | $26,000 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | $19,500 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | $19,500 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | $19,500 26 |
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October 2026
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| 1 | 2 | $19,500 3 | ||||
| 4 | 5 | 6 | 7 | 8 | 9 | $19,500 10 |
| 11 | 12 | 13 | 14 | 15 | 16 | $19,500 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $19,500 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $19,500 31 |
Available
Unavailable
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In the charming town of Edgartown, located on the west side of Cooke Street, this exquisite four-bedroom home features en suite bathrooms for each bedroom and a loft area for additional sleeping space. The interior is tastefully designed to embody the warmth and luxury of a coastal beach house. All bedrooms are situated on the upper levels, allowin
$27,000.00 - $32,500.00 / per week + taxes and fees
4
beds
6
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 45
In the charming town of Edgartown, located on the west side of Cooke Street, this exquisite four-bedroom home features en suite bathrooms for each bed... Read More
In the charming town of Edgartown, located on the west side of Cooke Street, this exquisite four-bedroom home features en suite bathrooms for each bed... Read More
August 2026
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September 2026
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| 1 | 2 | 3 | 4 | $27,000 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | $27,000 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | $27,000 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | $27,000 26 |
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October 2026
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| 1 | 2 | $27,000 3 | ||||
| 4 | 5 | 6 | 7 | 8 | 9 | $27,000 10 |
| 11 | 12 | 13 | 14 | 15 | 16 | $27,000 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $27,000 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $27,000 31 |
Available
Unavailable
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Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an equestrian estate, this six-bedroom, nine-bath home is perched on a hill, overlooking a pond and situated on nearly four acres in the Preserve. The impeccably designed interiors create a sense of pla
$17,500.00 - $34,000.00 / per week + taxes and fees
6
beds
9
Full Bath
sleeps
16
Pets Not Allowed
No Events/Gatherings
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
August 2026
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September 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | 2 | 3 | 4 | $27,500 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | $25,000 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | $25,000 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | $25,000 26 |
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October 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | 2 | $20,000 3 | ||||
| 4 | 5 | 6 | 7 | 8 | 9 | $20,000 10 |
| 11 | 12 | 13 | 14 | 15 | 16 | $20,000 17 |
| 18 | 19 | 20 | 21 | 22 | 23 | $20,000 24 |
| 25 | 26 | 27 | 28 | 29 | 30 | $17,500 31 |
Available
Unavailable
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