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Perfect Beach Front Cottage. Expansive Water Views, Gorgeous Sunsets, Pristine Modern Interior

Privately nestled atop a dune with breathtaking views and just steps from a private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun-filled rooms...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$4,040 - $7,090
June 2027
SuMoTuWeThFrSaWeek
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$5,530
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$5,530
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$5,530
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$5,530
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 $7,090
July 2027
SuMoTuWeThFrSaWeek
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$7,090
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$7,090
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$7,090
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$7,090
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$7,090
August 2027
SuMoTuWeThFrSaWeek
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$7,090
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$7,090
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$7,090
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$6,560
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 $6,040
September 2027
SuMoTuWeThFrSaWeek
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$6,040
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$5,510
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$4,990
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$4,990
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29
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 $4,460
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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PEALY

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Property Details
Newly Updated Chilmark Cottage, Key to Private association Black Point Beach just 8/10ths mile from Cottage

For those who love Chilmark! Located in a very private setting off of Quenames Rd, this fresh and modern updated cottage comes with a key to private association Black Point...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,500 - $3,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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PEDLF

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Property Details
Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
4
Baths: 
5
Price Range:
$18,500 - $22,500
June 2027
SuMoTuWeThFrSaWeek
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 $18,500
July 2027
SuMoTuWeThFrSaWeek
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$18,500
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$18,500
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$18,500
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$18,500
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$18,500
August 2027
SuMoTuWeThFrSaWeek
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$22,500
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$22,500
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$22,500
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$22,500
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 $22,500
September 2027
SuMoTuWeThFrSaWeek
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$22,500
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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PEMBT

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Property Details
Oak Bluffs Vacation Retreat – Exceptional Craftsmanship, Thoughtful Design & Unmatched Comfort, Sleep 8

Custom crafted with extraordinary attention to detail, quality, and comfort, this stunning Oak Bluffs vacation home offers an exceptional island getaway. Nestled in a peaceful residential neighborhood just two miles...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$4,500 - $12,000
June 2027
SuMoTuWeThFrSaWeek
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$5,500
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$6,500
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$7,500
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 $9,000
July 2027
SuMoTuWeThFrSaWeek
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$9,000
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$9,000
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$9,000
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$9,000
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$11,000
August 2027
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$12,000
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$10,000
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 $9,000
September 2027
SuMoTuWeThFrSaWeek
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$9,000
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$7,500
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$6,500
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$5,500
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 $5,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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PEOTA

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Property Details
Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks

This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond.  This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,000 - $5,350
June 2027
SuMoTuWeThFrSaWeek
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$3,550
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$3,550
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$4,050
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$4,770
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 $5,350
July 2027
SuMoTuWeThFrSaWeek
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$5,350
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$5,350
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$5,350
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$5,350
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$5,820
August 2027
SuMoTuWeThFrSaWeek
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$5,820
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$5,820
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$5,820
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$4,770
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 $3,550
September 2027
SuMoTuWeThFrSaWeek
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$3,550
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$3,050
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$3,050
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$2,550
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 $2,050
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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PERRG-1A-Patio.jpg
 
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PERRG

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Property Details
North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8 minute drive to Lucy Vincent Beach or Menemsha Village

Delightful, 3 bedroom, 2 bath home with AC. Private Chilmark hilltop location! This sweet home features an open kitchen, living, and dining area, and a screened porch for your summer...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,600 - $3,600
June 2027
SuMoTuWeThFrSaWeek
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$3,600
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$3,600
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$3,600
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$3,800
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 $3,800
July 2027
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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$3,800
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$4,000
August 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$3,800
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$3,600
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$3,600
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 $3,600
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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PETEO

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Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$0 - $0
June 2027
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July 2027
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September 2027
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PETEV

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Property Details
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home tucked away on the shores of Sengekontacket Lagoon in a community of homes - featuring gorgeous views, mini-split AC units in main living areas,...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $4,100
June 2027
SuMoTuWeThFrSaWeek
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$2,700
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$2,700
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$3,000
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$3,000
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 $3,500
July 2027
SuMoTuWeThFrSaWeek
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$3,500
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$4,100
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$3,900
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$3,900
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$4,100
August 2027
SuMoTuWeThFrSaWeek
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$4,100
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$4,100
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$4,100
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$4,100
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 $3,400
September 2027
SuMoTuWeThFrSaWeek
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$3,400
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$2,800
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$2,800
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$2,800
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 $2,800
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PHOUE

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Property Details
Sweet Cape Home, Gorgeous Water Views, Walk to Town, Lovely Landscaped Yard, Deck and Outdoor Dining Area.

Step into this impeccably clean Cape-style home and enjoy an open floor plan filled with natural light and serene waterviews.  The double living area offers multiple seating options, a TV, and...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$5,250 - $5,250
June 2027
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July 2027
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August 2027
SuMoTuWeThFrSaWeek
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$5,250
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$5,250
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$5,250
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$5,250
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Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PIKUT

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Property Details
Cozy Contemporary Home with Designer Interior Details , Centrally Located to Towns and Beaches

WELCOME TO SANDPIPER COTTAGE, YOUR STYLISH FAMILY RETREAT!

Four bedrooms include a primary bedroom with a queen bed on the 1st level with a television and a full bath across the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$1,600 - $2,600
June 2027
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September 2027
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

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