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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
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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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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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July 2026
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 $15,000
August 2026
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September 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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ENGLJ

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Property Details
Exquisite Estate Vacation Retreat, Main & Guest House, Affinity Pool, South Shore Waterviews, Sleeps 12 in 6 Bedrooms, Multiple Living & Entertaining Areas both indoors & out

Outstanding Chilmark Estate tucked on 9.5 private acres with sweeping views of the Atlantic Ocean and Chilmark Pond. This unique contemporary home features a heated infinity pool, screened porch, and expansive deck with...Read more

Location: 
Chilmark
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$35,000
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$35,000
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$35,000
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$40,000
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 $55,000
July 2026
SuMoTuWeThFrSaWeek
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$55,000
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$50,000
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$50,000
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$50,000
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 $60,000
August 2026
SuMoTuWeThFrSaWeek
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$60,000
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$60,000
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$60,000
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$60,000
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$50,000
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 $30,000
September 2026
SuMoTuWeThFrSaWeek
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$30,000
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$30,000
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$30,000
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$30,000
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Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7

Pool heated to 82 degrees in July and August included in rental rate

Pool heated to 82 degrees June & September additional surcharge $350 per week

Pool heated to 82 degrees May & October additional surcharge $450 per week

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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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ULYPA

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Property Details
Edgartown Retreat-Impeccably Maintained, Heated Pool -14 x 32', Screened Porch, Bluestone Patio, Exqusite Grounds and Gardens, Multiple Interior and Exterior Living Spaces

NOTE:  New for 2025: The owner is having a custom built 1 bedroom guest house added to the property that will sleep 2, featuring a living, dining, kitchen area, a bedroom,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$12,000
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 $15,000
July 2026
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
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$12,000
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September 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees included in rental rate July & August weeks. 

Pool Heat shoulder season weeks additional propane surcharge, please inquire! 

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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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ARONA

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Property Details
Superior New Luxury Build, Waterfront on the Lagoon, Multiple Indoor/Outdoor living Spaces. Private Association Beach Key, Deep Water Mooring

Nestled on Hines Point in Vineyard Haven, The Epitome of Summer Living offers sweeping vistas of the water from every room. With a sprawling screened porch, an upper-level deck, and...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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9
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$20,000
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 $20,000
August 2026
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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September 2026
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner provides a key to a beautiful  private association Beach in Chilmark, Quansoo Beach, approximately a 25 minute drive from the house. 

 

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GRAND

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Property Details
Lovely Edgartown Home, Private Location just 1.5 Miles to Village Center, Pool, 5 Bedrooms, 4.5 Baths, Sleeps 10

Charming 5-Bedroom, 4.5-Bath Home with Pool: Nestled in a private setting, this cozy home features a large above-ground pool, perfect for relaxation and fun, a private yard, and a large deck...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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2
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 $10,000
July 2026
SuMoTuWeThFrSaWeek
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$10,000
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$9,000
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$9,000
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$9,000
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 $10,000
August 2026
SuMoTuWeThFrSaWeek
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$10,000
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$12,000
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$12,000
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$12,000
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$12,000
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September 2026
SuMoTuWeThFrSa
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Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
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LORJU

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Property Details
Stunning Oak Bluffs Luxury Home with Heated Pool, Multiple Living Areas, Walk to Town 8/10ths mile from house.

This charming tri-level home is nestled on a peaceful street in the heart of Oak Bluffs, just a 10 to 15-minute walk from the town center, Inkwell Beach, Town Beaches,...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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2
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$13,500
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$13,500
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$13,500
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$13,500
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 $13,500
July 2026
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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$13,500
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 $15,000
August 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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$13,500
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 $13,500
September 2026
SuMoTuWeThFrSaWeek
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$13,500
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$8,000
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$8,000
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$8,000
27
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees, included in the rental rate!

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STEVK

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Property Details
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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2
3
4
5
6
$1,700
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$1,700
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$1,700
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$1,700
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 $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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 $2,500
August 2026
SuMoTuWeThFrSaWeek
 1
$2,500
2
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4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$2,800
23
24
25
26
27
28
29
$2,500
30
31
 $1,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,700
6
7
8
9
10
11
12
$1,700
13
14
15
16
17
18
19
$1,700
20
21
22
23
24
25
26
$1,700
27
28
29
30
 
Clean Fee: 
$180 per week
Tax: State & Local: 
11.7

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