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SWEET 3-BEDROOM, 3-BATH CHILMARK COTTAGE, SPACIOUS SCREENED PORCH AND DECK AREAS, OUTDOOR SHOWER; PRIVATE LOCATION ON 4 ACRES, 10 MINUTES TO LUCY VINCENT AND LONG POINT BEACHES

Charming updated summer home features a dining room that seats six, well-stocked kitchen, living room, plus screen porch with ceiling fan, dining table and chairs for 8, and reading/lounging nooks, leading...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,480 - $3,480
June 2026
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Clean Fee: 
$300 per week, $200 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7
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Seaview Condominium, Waterview, Walk to Town and Beach

Beachfront Condominium with breathtaking views of Nantucket Sound. Just steps to the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2026
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September 2026
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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Sea View Condominium, Water View, Walk to town and beach

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
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: 
$275 per week
Tax: State & Local: 
11.7
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Lovely All Newly Furnished Home, Walk to Vineyard Haven Village Center

Perfectly located for those who love to walk! Vineyard Haven Yacht Club, Main St with its lovely shops, and the Vineyard Haven library are all within a 10-minute walk from...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $5,900
June 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,960
14
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$3,960
21
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$3,960
28
29
30
 $4,860
July 2026
SuMoTuWeThFrSaWeek
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3
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$4,860
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$5,600
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$5,600
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$5,600
26
27
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30
31
 $5,700
August 2026
SuMoTuWeThFrSaWeek
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$5,700
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$5,900
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$5,900
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$5,400
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$5,310
30
31
 $4,860
September 2026
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$4,860
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$4,860
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

 

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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:
$4,900 - $5,900
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
SuMoTuWeThFrSaWeek
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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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Sengekontacket - Waterfront Cottage, Panoramic Views and Amazing Sunrises

Charming Vintage Summer Cottage on Sengekontacket Pond

Experience the beauty of this vintage cottage perched on the shores of Sengekontacket Pond, offering stunning water views across the pond to North...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,400 - $3,900
June 2026
SuMoTuWeThFrSaWeek
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$1,900
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$1,900
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$1,900
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$1,900
28
29
30
 $3,900
July 2026
SuMoTuWeThFrSaWeek
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$3,900
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$3,900
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$3,900
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$3,900
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 $3,900
August 2026
SuMoTuWeThFrSaWeek
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$3,900
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$3,900
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$3,900
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$3,900
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$3,900
30
31
 $2,500
September 2026
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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 $2,500
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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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
28
29
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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
30
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 $5,000
September 2026
SuMoTuWeThFrSaWeek
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$5,000
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Tucked in the Heart of the Katama area of Edgartown, Charming, Spacious, Open Floor Plan Garage Apartment

Perfect Summer Getaway in Katama

Enjoy your summer escape in this spacious and immaculate apartment, ideally located in the heart of Katama—just one mile from South Beach and two miles...Read more

Location: 
Edgartown
Sleeps: 
2
Bedrooms: 
1
Baths: 
1
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$1,700
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$1,700
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$1,700
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$1,700
28
29
30
 $2,500
July 2026
SuMoTuWeThFrSaWeek
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2
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$2,500
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$2,500
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$2,500
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$2,500
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30
31
 $2,500
August 2026
SuMoTuWeThFrSaWeek
 1
$2,500
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$3,000
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$3,000
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$2,800
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$2,500
30
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 $1,700
September 2026
SuMoTuWeThFrSaWeek
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$1,700
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$1,700
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$1,700
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$1,700
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29
30
 
Clean Fee: 
$180 per week
Tax: State & Local: 
11.7
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South Beach Edgartown, WiFi, Central A/C

This 3 bedroom, 2 bath immaculate Katama Cape is conveniently located 2 miles to the beach and 1.5 miles to Edgartown Center.  Comfortable, bright interior and great yard and deck...Read more

Location: 
Katama
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: 
$250 per week
Tax: State & Local: 
11.7
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Ocean View House! Luxury Main & Guest, Waterfront on the Vineyard Sound, Association Beach, 5 Bedrooms, 3 Baths

Stunning Spring Point Vacation Retreat! This newly renovated Main & Guest House is situated in a 335 acre parcel of Chilmark with approximately 40 homes scattered throughout the acreage, and is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$15,000 - $30,000
June 2026
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
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$15,000
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 $25,000
July 2026
SuMoTuWeThFrSaWeek
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$25,000
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$25,000
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$25,000
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$25,000
26
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30
31
 $25,000
August 2026
SuMoTuWeThFrSaWeek
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$25,000
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$25,000
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$25,000
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$25,000
23
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$25,000
30
31
 $17,000
September 2026
SuMoTuWeThFrSaWeek
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$17,000
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$17,000
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$15,000
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$15,000
27
28
29
30
 $15,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner reduced rates for August weeks - see calendar for rates

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