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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 - $11,000
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
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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: 
14.45
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PAILB

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Property Details
Exquisite all Newly Updated Contemporary Farm House Style Home! Heated Pool! Location!! 15 minute walk to Edgartown Village Center, 5 minute Drive to South Beach

Outstanding Edgartown Vacation Home!  Walk or bike to the center of Edgartown Village from this handsomely crafted, 5-bedroom, 3.5-bath vacation home. Multiple living spaces flow seamlessly from inside to the vaulted, 3-season screened...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,980 - $10,970
June 2027
SuMoTuWeThFrSaWeek
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$10,970
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$10,970
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$14,980
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$14,980
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 $16,970
July 2027
SuMoTuWeThFrSaWeek
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$16,970
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$16,970
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$16,970
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$16,970
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$16,970
August 2027
SuMoTuWeThFrSaWeek
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$17,970
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$17,970
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$17,970
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$17,970
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 $13,980
September 2027
SuMoTuWeThFrSaWeek
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$13,980
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$10,970
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$10,970
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$10,970
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 $8,980
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

Pool Heat to 82 degrees, included in rental rate July & August

Pool Heat to 82 degrees,  Shoulder season weeks additional $275 per week

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ANGE5

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Property Details
Classic Edgartown Village Home with Lovely Water View, Walk to Beach

Sophisticated charm, gorgeous two bedroom, two bath home set on a quiet lane with water views and beautifully landscaped yard. Located just a short walk to Fuller St Beach. Modern design...Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$5,000 - $10,500
June 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$8,000
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 $10,000
July 2027
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 2027
SuMoTuWeThFrSaWeek
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$10,500
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$10,500
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$10,500
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$10,500
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 $10,500
September 2027
SuMoTuWeThFrSaWeek
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$10,500
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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: 
$300 per week
Tax: State & Local: 
11.7
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KERR4

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Property Details
Sophisticated & Charming Waterfront Cottage, Large Waterfront Deck, Dock, Tennis Court, Spectacular Views

Stunning cottage style home where the wate front is literally at your doorstep. Lake Tashmoo is a large saltwater inlet great for swimming, sailing, and boating with access to the ocean.  Relax on the...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$9,900 - $10,000
June 2027
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July 2027
SuMoTuWeThFrSaWeek
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$9,900
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$9,900
August 2027
SuMoTuWeThFrSaWeek
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$9,900
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$10,000
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$9,900
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$9,900
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 $9,900
September 2027
SuMoTuWeThFrSaWeek
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$9,900
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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WIL14

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Property Details

Classic updated 7 bedrooms, 5 bath West Chop Home. Nestled on a large landscaped lot on Hatch Rd in Vineyard Haven this spacious home offers the best in vacation home...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
7
Baths: 
5
Price Range:
$10,000 - $10,000
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: 
$1000 per week
Tax: State & Local: 
11.7
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MAL24

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Property Details
Gorgeous, Classic, Spacious New England Home, Main & Carriage House, In the Heart of the Katama Area of Edgartown, Multiple Living Spaces both Inside & Out, Sleeps 10. Private Landscaped Grounds. Multiple Decks, Screened Porch

Experience the essence of modern living in an exquisite New England home boasting classic design, nestled on meticulously landscaped grounds just moments away from South Beach and Edgartown Village.

The Main...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$10,000 - $10,000
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: 
$1250 per week
Tax: State & Local: 
11.7
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HUN28

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Property Details
Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

This stylish contemporary retreat is ideally located in a lovely, peaceful Oak Bluffs neighborhood, just a 10–15 minute stroll to the village center, parks, Inkwell Beach, Oak Bluffs Town Beach, and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,250 - $9,760
June 2027
SuMoTuWeThFrSaWeek
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$9,760
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$9,760
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$9,760
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$9,760
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 $9,760
July 2027
SuMoTuWeThFrSaWeek
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$9,760
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$10,460
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$10,460
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$10,460
25
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$10,460
August 2027
SuMoTuWeThFrSaWeek
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$13,960
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$13,960
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$13,960
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$13,960
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 $13,960
September 2027
SuMoTuWeThFrSaWeek
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$13,960
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$9,060
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$6,650
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$6,650
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 $6,650
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

2026, Owner offers 10% discount off rental rate - May, June, July weeks for 7 night stay or longer. 

 

3 night minimum stay required, May, June to last week, September 5 on &, October. 

 

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RUNYW

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Property Details
Water view Upper Makonikey Home, Distinctive Design by Royal Barry Wills, Two Private Association Beaches, Central A/C

Classic Royal Barry Wills-designed cedar-shingled Vineyard home, beautifully sited on five private landscaped acres in the exclusive enclave of homes known as Makonikey. Lovely distant water views of Vineyard Sound and...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,000 - $9,750
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$5,000
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7
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$5,750
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$5,750
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$7,500
27
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 $9,750
July 2027
SuMoTuWeThFrSaWeek
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$9,750
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$9,750
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$9,750
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$9,750
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$9,750
August 2027
SuMoTuWeThFrSaWeek
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$9,750
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$9,750
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$9,750
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$9,750
29
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 $7,500
September 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$5,750
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$5,750
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29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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WE122

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Property Details
Luxury Modern Farm House Design, Waterfront Pear Tree Cove on the Tisbury Great Pond, Rental Boat Access to South Shore Beach, Spectacular Area for Kayak Enthusiasts

New exquisite contemporary farmhouse design! Waterfront on the Tisbury Great Pond with access via boat rentals to gorgeous South Shore Beach. The beach area on the pond provides a great play space...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$9,500 - $9,500
June 2027
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July 2027
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September 2027
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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VANA2

Inquire
Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $9,500
June 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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 $5,000
July 2027
SuMoTuWeThFrSaWeek
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$5,000
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$6,500
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$6,000
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$6,500
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$9,500
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$9,500
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$9,500
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$6,500
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 $5,000
September 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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 $4,500
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
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ARNOS

Inquire
Property Details
Wonderful Family Friendly Home in West Chop Area of Vineyard Haven
Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
6
Baths: 
3
Price Range:
$4,200 - $9,450
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$6,700
6
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$7,000
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$7,000
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$7,000
27
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 $8,400
July 2027
SuMoTuWeThFrSaWeek
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2
3
$8,400
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$8,400
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$8,400
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$8,400
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$8,400
August 2027
SuMoTuWeThFrSaWeek
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$9,450
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$9,450
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$9,450
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$9,450
29
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 $8,100
September 2027
SuMoTuWeThFrSaWeek
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$8,100
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$6,300
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$6,300
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$6,300
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 $6,300
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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SHANJ

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Property Details
Newly Remodeled Contemporary Farm House, 12 x 26 Saltwater Heated Pool, Walk to Town, Bike to the Beach

Exquisite newly remodeled home with just the right touch of coastal decor and modern styling. This perfectly situated picturesque home allows guests to walk to the village area and is an easy no...Read more

Location: 
Katama
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $9,400
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$5,450
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$6,800
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$6,800
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$9,400
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 $9,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,400
4
5
6
7
8
9
10
$9,700
11
12
13
14
15
16
17
$10,200
18
19
20
21
22
23
24
$10,200
25
26
27
28
29
30
31
$10,650
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,650
8
9
10
11
12
13
14
$10,650
15
16
17
18
19
20
21
$10,650
22
23
24
25
26
27
28
$7,800
29
30
31
 $6,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$6,000
12
13
14
15
16
17
18
$4,500
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
 $4,200
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Pool heated to 81 in July & August included in rental rate.  Additional $250 per week in off season.

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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $9,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$7,100
13
14
15
16
17
18
19
$7,700
20
21
22
23
24
25
26
$8,400
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,000
4
5
6
7
8
9
10
$9,000
11
12
13
14
15
16
17
$9,400
18
19
20
21
22
23
24
$9,700
25
26
27
28
29
30
31
$9,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,200
8
9
10
11
12
13
14
$11,700
15
16
17
18
19
20
21
$11,200
22
23
24
25
26
27
28
$10,000
29
30
31
 $8,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,400
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
 $4,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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FREE2

Inquire
Property Details
Lovely Historic William St Home, Located just one block from Main St. 4 bedrooms, 4 baths

Beautifully renovated Greek Revival home (the Berkshire House) on historic William Street in Vineyard Haven.

This finely crafted home offers vacationing guests spacious living on three levels. The main level...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,900 - $9,250
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,250
4
5
6
7
8
9
10
$9,250
11
12
13
14
15
16
17
$9,250
18
19
20
21
22
23
24
$9,250
25
26
27
28
29
30
31
$9,250
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,250
8
9
10
11
12
13
14
$9,250
15
16
17
18
19
20
21
$9,250
22
23
24
25
26
27
28
$9,250
29
30
31
 
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
$6,900
12
13
14
15
16
17
18
$6,900
19
20
21
22
23
24
25
$5,900
26
27
28
29
30
 $5,900
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

 

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GOLDF

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Property Details
Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$9,000 - $9,000
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,000
8
9
10
11
12
13
14
$14,000
15
16
17
18
19
20
21
$14,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $9,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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