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Outstanding, Newly Updated Vacation Retreat, Heated Saltwater Pool. Multiple Living Spaces, All New Kitchen, Gorgeous Yard, Set in Quiet, Lovely Commmunity of Homes, Stonegate

Impeccable Vacation Getaway with Updated Amenities and a Heated Saltwater Pool

Nestled within the serene community of Stonegate, this exceptional retreat offers a rejuvenating escape. Conveniently located just a brief...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$11,000
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$11,000
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 $13,000
July 2026
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$13,000
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$13,000
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$13,000
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$13,000
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 $16,000
August 2026
SuMoTuWeThFrSaWeek
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$16,000
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$16,000
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$14,000
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 $11,000
September 2026
SuMoTuWeThFrSaWeek
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$11,000
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$8,000
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$8,000
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$8,000
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 $8,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Rate reduced for the last week in August - see calendar for rate

Pool heated to 82 July & August included in rental rate.  

Spa area in the pool is heated to the same temperature as the pool and is not available Spa jets are also not available for renter use. 

 

Pool heated to 82 June & September when weeks are available additional $300 per week propane surcharge.

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LANLL

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Property Details
Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2026
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August 2026
SuMoTuWeThFrSaWeek
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$18,000
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$15,500
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 $15,500
September 2026
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$15,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Two Week Minimum Stay Required per Owner

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PLACH

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Property Details

Note:  Pool is heated by solar panels so the temperature cannot be set. Generally is in the 80's during the latter part of June through the first week of September.  ...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
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STA50

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Property Details
Adorable 2 Bedroom, 1 Bath Cottage, Large Private Back Yard, Deck, Walk to Vineyard Haven Center

Adorable light-filled cottage, with modern furnishings, this lovely 2 bedroom home is situated on a large lot on a quiet street just on the outskirts of Vineyard Haven Center.  The home has a...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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 $4,900
July 2026
SuMoTuWeThFrSaWeek
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$4,900
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$4,900
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$4,900
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$4,900
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 $5,900
August 2026
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$5,900
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$5,900
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$5,900
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$5,900
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$4,900
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 $4,900
September 2026
SuMoTuWeThFrSaWeek
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$4,900
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$4,900
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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KELVH

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Property Details
Classic Main St Home, Stylish Updates, Beautifully Landscaped, Porch overlooks Yard, Walk to Town Center

Classic Vineyard Haven Main St Home!  Recently updated throughout and is being offered as a vacation rental, ideal for families of 6.  Multiple living spaces assure that all have room to...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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ELLIK

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Property Details
Quintessential West Chop Waterfront Home. Private Beach, Spectacular Views

Enjoy the essence of summer at this waterfront home with a private beach just 50 yards in front of the house. Evenings enjoy the magnificent sunsets while relaxing on the...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$25,000
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 $28,000
July 2026
SuMoTuWeThFrSaWeek
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$28,000
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$25,000
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$25,000
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$25,000
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 $28,000
August 2026
SuMoTuWeThFrSaWeek
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$28,000
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$28,000
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$28,000
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$28,000
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$28,000
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 $25,000
September 2026
SuMoTuWeThFrSaWeek
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$25,000
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$17,500
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$17,500
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$17,500
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 $17,500
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
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NEWMJ

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Property Details

Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BURET

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Property Details
Pristine Cape, Located on a Large Lot in Bold Meadow Area of Edgartown, Large Yard, Sleeps 8

The perfect vacation home sits on a large lot with a beautifully landscaped private yard bordered by woodlands.  Bold Meadow is a lovely private enclave of homes on the outskirts of...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$525 per week
Tax: State & Local: 
11.7
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STEJE

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Property Details
Charming Oak Bluffs Home, Waterfront on the Lagoon, Patio & Deck Areas. Spectacular Views & Sunsets

Waterfront on the Lagoon! The highlight of this home is its breathtaking views across the lagoon and beautiful sunsets. Whether you're inside or outside on the deck or patio, you can...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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 $7,400
July 2026
SuMoTuWeThFrSaWeek
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$7,400
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$7,400
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$7,400
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$7,400
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 $8,500
August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$10,500
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$10,500
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$11,500
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 $5,000
September 2026
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$5,000
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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ROBDE

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Property Details
Edgartown, Katama Area, Spacious Luxury with Designer Detailing, Chef's Kitchen, Multiple Living Spaces, 4 Bedrooms, 3.5 Baths

New in 2022 large addition and full renovation to this beautiful Katama home. Located within walking distance of town (1.4 miles) and biking to Katama South Beach (2.1 miles). 

The...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Sales Tax Exempt for weeks 8/8 & 8/15

 

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MANUC

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Property Details
Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
July 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
August 2026
SuMoTuWeThFrSaWeek
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$10,000
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$11,000
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$11,000
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$11,000
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 $10,000
September 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BROW2

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Property Details
Heated Pool, 10 x 16. Edgartown Village Center, Walk to Town, Sleeps 6, South and State Beaches 10 to 12 minute drive.

Beautiful new in-town home with heated pool,screened porch, a lovely, landscaped yard with expansive lawn area and nicely tucked on a quiet street just a 10-minute walk from the Edgartown...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
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August 2026
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September 2026
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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LONAJ

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Property Details
Luxurious Oak Bluffs Home, Multiple Living Spaces, Deck Dining Area. 3 Bedrms, Sleeps7

Welcome to this exquisite, contemporary, luxurious Oak Bluffs residence. Nestled on a tranquil street on the periphery of Oak Bluffs, this 3-bedroom, 2.5-bathroom home boasts opulent accents throughout.

Upon entry...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

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WILLC

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Property Details
Beautiful, Spacious Contemporary Home, Sleeps 8, Tucked on a large lot in an Enclave of Lovely Homes

Nestled amidst  lovely landscaped grounds, this contemporary vacation getaway offers ample space and modern comforts. A serene path from the backyard invites exploration of nearby walking trails. Boasting multiple living areas...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$600
Tax: State & Local: 
11.7
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LEAHW

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Property Details
Spacious West Tisbury Home, Multiple Indoor, Outdoor living Spaces. 4 bedrooms, 5 Min Drive to Lambert's Cove Beach

Nestled off the serene Hidden Village Rd, merely 1.5 miles away from Lambert’s Cove Beach, this charming, spacious home offers contemporary comforts in a secluded haven. With a blend of...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

 

 

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