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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The Sweetest In-town Cottage! 2 Minute Walk to Main St

This adorable cottage-style home features 2 bedrooms, and 2 baths and is tucked in on a tiny side street off of Main St. Walk to all that the village center...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,200 - $4,200
June 2027
SuMoTuWeThFrSaWeek
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$3,700
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$3,700
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$3,700
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$3,700
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 $4,000
July 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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$4,200
August 2027
SuMoTuWeThFrSaWeek
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$4,200
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$4,200
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$4,400
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$4,400
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 $3,200
September 2027
SuMoTuWeThFrSaWeek
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$3,200
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$3,200
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$3,200
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29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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THEOK~

Inquire
Property Details
Lovely Cape Home, Newly Updated, Private Back Deck with Outdoor Dining & Grill, 3 Bedrooms w/AC and TV, 1.5 baths

Nestled on a serene lane in the outskirts of Vineyard Haven, this newly updated & charming Cape Style residence exudes chic charm. Step inside to discover an inviting open layout...Read more

Location: 
Vineyard Haven
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $4,000
June 2027
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,500
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 $3,700
July 2027
SuMoTuWeThFrSaWeek
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$3,700
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$3,700
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$3,700
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$3,700
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$4,000
August 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,400
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$4,400
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$4,000
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 $3,500
September 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,000
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$3,000
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$3,000
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 $3,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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KRAFM~

Inquire
Property Details
Pristine Bungalow, Peekaboo Water View of Lagoon, Private Path to the Lagoon Waterfront from the Yard, 2 Kayaks Provided

THOREAU'S SPIRIT LIVES - An original 1920's summer bungalow lovingly restored to perfection. Two plus acres of quiet comfort, surrounded by farmland and woods. Walk down the long lawn past...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $3,800
June 2027
SuMoTuWeThFrSaWeek
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$2,000
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$2,400
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$2,400
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$3,050
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 $3,250
July 2027
SuMoTuWeThFrSaWeek
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$3,250
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$3,250
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$3,250
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$3,500
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$3,500
August 2027
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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$3,500
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 $2,100
September 2027
SuMoTuWeThFrSaWeek
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$2,100
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$2,100
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$2,100
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$2,100
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 $2,100
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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ARNOP

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Property Details
West Chop Area, Central Air

Country Cottage Retreat. This completely renovated gem is located just at the head of the West Chop area in Vineyard Haven. The interior layout features four bedrooms, 2.5 baths, a...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$4,000
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 $5,800
July 2027
SuMoTuWeThFrSaWeek
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$5,800
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$5,800
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$5,800
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$5,800
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$5,800
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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 $4,250
September 2027
SuMoTuWeThFrSaWeek
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$4,250
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$3,500
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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ROBER

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Property Details
Cozy, newly updated Vineyard Haven Cottage, 2 Bedrooms, 1 Bath, Sleeps 4. Spacious Deck with Dining Area & Grill

Nestled on the outskirts of Vineyard Haven, this charming cottage is ideal for small families or two couples seeking a serene retreat. Just a leisurely 15-minute stroll from Main St,...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$2,000 - $3,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
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$2,700
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$2,700
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$2,700
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$3,500
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 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
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$3,500
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$3,500
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$3,500
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$3,500
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$3,500
August 2027
SuMoTuWeThFrSaWeek
1
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$3,500
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$3,500
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$3,500
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$3,500
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30
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 $3,000
September 2027
SuMoTuWeThFrSaWeek
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2
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$3,000
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$2,500
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$2,500
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$2,500
26
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29
30
 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ADELC~

Inquire
Property Details
Cozy Sunny 3 Bedroom Contemporary, Spacious Deck, Situated in a Quiet Neighborhood just on the outskirts of Vineyard Haven Village Center

Located on a quiet residential circle in Vineyard Haven, this pristine sweet home with oversized windows is contemporary, yet rustic with exposed wooden beams and a cathedral ceiling.  New natural travertine...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$2,750 - $2,750
June 2027
SuMoTuWeThFrSaWeek
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 $2,750
July 2027
SuMoTuWeThFrSaWeek
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$2,750
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$2,750
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August 2027
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September 2027
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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FERGN

Inquire
Property Details
5 minute walk to town center.

Enjoy a view of Vineyard Haven harbor from this 1898 Captain's home. Walk to town, tennis, dining, library, etc... The Captain Henry Stevenson house has been renovated to include a...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$0 - $0
June 2027
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July 2027
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GRUNM

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Property Details
Waterfront & Beachfront

The Beach House  There are few homes anywhere on the island directly on a sandy swimming beach like Beach House. If you love a sunset, and water views that seemingly never...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$600
Tax: State & Local: 
11.7
Add Favorite
 
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HALLL~

Inquire
Property Details
Makonikey, Water View, Walk to Private Association Beach, Large Yard Area.

Located in Makonikey,  a private enclave of homes on the North Shore.

Beautifully maintained four-bedroom vacation home with water views. Just a short walk or drive to private Makonikey association beach,  This...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
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10
$4,800
11
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$4,800
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$4,800
25
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$4,800
August 2027
SuMoTuWeThFrSaWeek
1
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$4,800
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$4,800
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
urmst-01-exterior.jpg
 
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URMST

Inquire
Property Details
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 2027
SuMoTuWeThFrSaWeek
 1
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 $15,600
July 2027
SuMoTuWeThFrSaWeek
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$15,600
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$15,600
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$15,600
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$15,600
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$15,600
August 2027
SuMoTuWeThFrSaWeek
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$15,600
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$15,600
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$15,600
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$15,600
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September 2027
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Clean Fee: 
$875 per rental period
Tax: State & Local: 
11.7
Add Favorite
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KERR3

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Property Details
Waterfront on the Shores of a Picturesque Tidal Inlet Lake Tashmoo, Shared Tennis Courts, Spectacular Views & Sunsets,

This lovely three-bedroom home is located on the shores of beautiful Lake Tashmoo (a tidal saltwater lake connecting to Vineyard Sound).  The modern open floor plan includes. kitchen, living, and...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$8,500
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$8,500
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 $8,500
September 2027
SuMoTuWeThFrSaWeek
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$8,500
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30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GEARP

Inquire
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 2027
SuMoTuWeThFrSaWeek
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 $6,250
July 2027
SuMoTuWeThFrSaWeek
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$6,250
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$6,250
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$6,250
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$6,950
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$7,550
August 2027
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$7,550
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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SANBG

Inquire
Property Details
Gorgeous Water views, set in private Mink Meadows Golf Course Community , Private Association Beach, Walk or drive to the Golf Course Club House

Beautiful home in Mink Meadows area of West Chop.  Guests will enjoy the gorgeous water views across Mink Meadows Pond to the North Shore. Swans, geese, and ducks reside in the...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2027
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$5,200
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$5,200
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$5,200
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 $7,750
July 2027
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$7,750
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$7,750
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$7,750
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$7,750
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$7,900
August 2027
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$7,900
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$7,900
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$7,900
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$7,900
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 $4,500
September 2027
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$4,500
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$4,500
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$4,500
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$4,500
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

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DRAPG~

Inquire
Property Details
Mink Meadow Guest Cottage, Overlooks Golf Course, Walk to Beach 5 min walk from House, Mink Meadows Golf Course, 1 mile to Clubhouse

Cozy guest cottage with designer touches throughout. As the guest cottage to the main house, this adorable cottage is private from the main house and has its own drive and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$0 - $0
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: 
$150 per week
Tax: State & Local: 
11.7
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DRAPM~

Inquire
Property Details
Mink Meadows Family Compound, Private Heated Pool, Walk or Drive to Private Association Beach, Beautifully Landscaped Yard, Deck and Patio, Golf 1 Mile from House

Spacious 4 Bedroom, 3.5 bath family compound with 28 x 14  heated pool, multiple indoor/outdoor living spaces situated in Mink Meadows Association. 

Mink Meadows Public Golf Course is just a short drive...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
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: 
$550 per week
Tax: State & Local: 
11.7

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

 

Pool heated to 81 degrees June & September additional $250 per week. Requests for higher temperature, please contact your agent for details. 

 

Pool heated to 81 degrees May & October additional $350 per week. Requests for higher temperature, please contact your agent for details.

 

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