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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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 - $3,600
June 2026
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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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 $3,050
July 2026
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$3,050
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$3,050
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$3,050
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$3,300
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 $3,300
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 $2,100
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$2,100
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Clean Fee: 
$375 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 2026
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$2,700
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$2,500
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 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MILLR

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Property Details
Tashmoo Cove Condominium, Association Pool, Tennis and Beach, Central Air

Set in Tashmoo Woods, an enclave of private homes and condominium units with association amenities,- pool and tennis courts just a short walk from the unit. This unit has a private deck with...Read more

Location: 
Vineyard Haven
Sleeps: 
5
Bedrooms: 
2
Baths: 
3
Price Range:
$2,770 - $3,000
June 2026
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 $2,770
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Owner requires two week minimum in August and must be either 8/2 to 8/16 or 8/16 to 8/30 

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ADELC

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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:
$2,500 - $2,500
June 2026
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$2,400
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 $2,500
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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DRAPG

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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:
$1,900 - $2,100
June 2026
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$1,900
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$1,900
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$1,900
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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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 $1,900
September 2026
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$1,900
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$1,900
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$1,900
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 $1,900
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
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FIELR

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Property Details
Exquisite West Chop Waterfront Home, Panoramic Ocean Views, Beach, Less than a Mile to Town Center

Grand West Chop Home, designed by a noted Vineyard Architect to highlight the magnificent water views. Surrounded by lush grounds and featuring an expansive bluestone patio perfect space to gather, dine, relax, and take...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$675 per week
Tax: State & Local: 
11.7
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BAYLM

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Property Details
Spectacular Waterfront Views in exclusive Makonikey area, Ocean Views and Breathtaking Sunsets, Private Beach, Private Location

This serene waterfront retreat offers sweeping water views in an exceptionally private setting, yet is just a 10-minute drive from town, with access to fine dining, shopping, galleries, and entertainment....Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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 $11,000
August 2026
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MCMAE

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Property Details
Light Filled, Stylish Cape Home, Ideal Central Location to Vineyard Haven, Oak Bluffs, Edgartown and Public Beaches.

Sure to please, this lovely all-new custom Cape is bordered by lawn and tall oaks and features a spacious open floor plan in the main living level with a dormered...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
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Clean Fee: 
$380 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
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

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