Vineyard Haven Vacation Rentals

Vineyard Haven, Martha’s Vineyard’s primary port town, is the perfect place for vacation rental guests who want to be close the action. While staying in a Vineyard Haven vacation rental, you have direct access to the waterfront and Vineyard Haven’s many fun events, world-famous restaurants, and classic bars. Vacations in Vineyard Haven are full of excitement and fun on the water, and going out in Vineyard Haven after a day at the beach gives you the classic Martha’s Vineyard experience.

 

 

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West Chop, Waterfront, Private Beach

Summer Compound in a majestic location.  Vintage vacation home perfect for large family gatherings.  Enjoy sweeping ocean views from the large comfortably furnished veranda.  A large screened porch offers seating...Read more

Location: 
Vineyard Haven
Sleeps: 
14
Bedrooms: 
6
Baths: 
2
Price Range:
$0 - $0
June 2026
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 $15,600
July 2026
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$15,600
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Clean Fee: 
$875 per rental period
Tax: State & Local: 
11.7
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GEARP

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Property Details
Stunning Historic Home, Nicely Renovated with Luxury Details throughout, AC, View of Harbor from 2nd Level Porch

Quintessential, historic in-town Vineyard home, just steps from the beach and ferry.  Water views of Vineyard Haven Harbor. This totally renovated house is designed to create the perfect Vineyard vacation. ...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
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 $6,250
July 2026
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$6,950
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 $7,550
August 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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TAVAM

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Property Details
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
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$11,000
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$11,000
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 $13,000
July 2026
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 $16,000
August 2026
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$16,000
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 $11,000
September 2026
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 $8,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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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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
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 $4,900
July 2026
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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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$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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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
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$28,000
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 $28,000
August 2026
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$28,000
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$28,000
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 $25,000
September 2026
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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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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
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$20,000
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 $20,000
August 2026
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$20,000
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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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