Vineyard Haven

Tisbury, also known by its Village name Vineyard Haven, has a rich and deep maritime tradition and was once one of early New England's busiest ports. Today, you can saunter through art galleries, visit a variety of shops and restaurants, and swing by the famous Bunch of Grapes Bookstore, a favorite shopping spot for Barack and Michelle Obama and dozens of writers who hope for one of the summer signing spots at the store. If the history and culture of the island are of interest, MV Museum’s new campus is perched overlooking the Lagoon and is well worth a visit – the exhibits and events are ever changing throughout the summer. Vineyard Haven harbor is a working harbor with ship building and repair carried on in several waterfront buildings. A fun place to watch the activity is from the popular Black Dog Tavern adjacent to the ferry terminal. There are several small public beaches in Tisbury – whichever you choose, the views are always active, and the parking is limited so arrive early.



Properties Available 52 properties available
Lovely two bedroom guesthouse in Mink Meadows with one bedroom on the first floor and one in the closed loft area above. Television in both bedrooms and living room. Small outdoor deck off the side of the house. The Main house can be rented separately (rental property number 1223 for more details).
Vineyard Haven
$1,900.00 - $2,100.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Vineyard Haven 1224
Lovely two bedroom guesthouse in Mink Meadows with one bedroom on the first floor and one in the closed loft area above. Television in both bedrooms a... Read More
June 2027
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    1 2 3 4 $1900 5
6 7 8 9 10 11 $1900 12
13 14 15 16 17 18 $1900 19
20 21 22 23 24 25 $1900 26
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July 2027
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        1 2 $2100 3
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11 12 13 14 15 16 $2100 17
18 19 20 21 22 23 $2100 24
25 26 27 28 29 30 $2100 31
August 2027
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1 2 3 4 5 6 $2100 7
8 9 10 11 12 13 $2100 14
15 16 17 18 19 20 $2100 21
22 23 24 25 26 27 $2100 28
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Vineyard Haven's Historic District is host to the 1805 Edmund Crowell House. This 5-bedroom home overlooks Vineyard Haven harbor, just steps from the town beach. Inside enjoy the preserved vintage features such as high ceilings, wide-board floors, and parlor with shiplap wainscoting. Cook in the large well-appointed kitchen with "antique" applia
Vineyard Haven Pet Friendly
$7,000.00 - $8,500.00 / per week
Beds 5 beds
Baths 4 Full Bath
Sleeps 8 sleeps
Vineyard Haven 1244
Vineyard Haven's Historic District is host to the 1805 Edmund Crowell House. This 5-bedroom home overlooks Vineyard Haven harbor, just steps from the... Read More
June 2027
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Beautiful Three-Bedroom Tashmoo Cove Condo - Experience the best of island living in this lovely end-unit condo, ideally situated in the sought-after Tashmoo Cove community. The open-concept floor plan features central air conditioning, granite countertops, and stainless steel appliances, creating a comfortable and contemporary retreat. The first f
Hot HOT 15
Vineyard Haven
$2,600.00 - $3,500.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 6 sleeps
Rating 4.4 (5)
Vineyard Haven 916
Beautiful Three-Bedroom Tashmoo Cove Condo - Experience the best of island living in this lovely end-unit condo, ideally situated in the sought-after ... Read More
June 2027
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    1 2 3 4 $3000 5
6 7 8 9 10 11 $3000 12
13 14 15 16 17 18 $3000 19
20 21 22 23 24 25 $3500 26
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        1 2 $3500 3
4 5 6 7 8 9 $3500 10
11 12 13 14 15 16 $3500 17
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25 26 27 28 29 30 $3500 31
August 2027
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8 9 10 11 12 13 $3500 14
15 16 17 18 19 20 $3500 21
22 23 24 25 26 27 $3000 28
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Experience this spectacular home located on Lagoon Pond just minutes from Vineyard Haven and Oak Bluffs. This three-bedroom, three-bath home offers unparalleled views of the lagoon, with a private beach and mooring just a few steps away from the spacious outdoor deck. Wake up to the soothing sounds of hummingbirds, cranes, kingfishers, and ospreys
Vineyard Haven
$7,500.00 - $10,500.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Vineyard Haven 1253
Experience this spectacular home located on Lagoon Pond just minutes from Vineyard Haven and Oak Bluffs. This three-bedroom, three-bath home offers un... Read More
June 2027
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    1 2 3 4 $7500 5
6 7 8 9 10 11 $7500 12
13 14 15 16 17 18 $7500 19
20 21 22 23 24 25 $9700 26
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18 19 20 21 22 23 $10250 24
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22 23 24 25 26 27 $9900 28
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Relax on the front porch of this recently renovated cottage within just blocks to all the shops, the Steamship Authority and Owen Park Beach. This home has all the amenities needed for an enjoyable vacation including central air conditioning.
Vineyard Haven
$3,500.00 - $6,000.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 7 sleeps
Vineyard Haven 915
Relax on the front porch of this recently renovated cottage within just blocks to all the shops, the Steamship Authority and Owen Park Beach. This hom... Read More
June 2027
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    1 2 3 4 $3800 5
6 7 8 9 10 11 $3800 12
13 14 15 16 17 18 $3900 19
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With a sprawling front lawn and salt water pool, this well-appointed five bedroom home has plenty of room for friends and family alike. Renovated and redecorated in a sophisticated coastal scheme: calming hues of blue, ivory and tan. There are multiple living areas so everyone has a bit of downtime, central air conditioning, an eat-in kitchen and a
Hot HOT 13
Vineyard Haven
$7,000.00 - $12,000.00 / per week
Beds 5 beds
Baths 3 Full, 1 Half Bath
Sleeps 10 sleeps
Rating 5 (2)
Vineyard Haven 901
With a sprawling front lawn and salt water pool, this well-appointed five bedroom home has plenty of room for friends and family alike. Renovated and ... Read More
June 2027
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    1 2 3 4 $7000 5
6 7 8 9 10 11 $7000 12
13 14 15 16 17 18 $7000 19
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July 2027
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4 5 6 7 8 9 $11000 10
11 12 13 14 15 16 $11000 17
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August 2027
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15 16 17 18 19 20 $12000 21
22 23 24 25 26 27 $9000 28
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Discover this lovely four-bedroom Cape-style home fully equipped and nestled in Vineyard Haven, featuring an expansive deck and a charming farmer's porch. Enjoy private access to Tashmoo Pond, perfect for afternoons spent kayaking and evenings gathered around the fire pit. Recently updated, this home is ready to provide a wonderful Vineyard vacatio
Vineyard Haven Pet Friendly
$3,500.00 - $7,500.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Vineyard Haven 905
Discover this lovely four-bedroom Cape-style home fully equipped and nestled in Vineyard Haven, featuring an expansive deck and a charming farmer's po... Read More
June 2027
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    1 2 3 4 $5000 5
6 7 8 9 10 11 $5000 12
13 14 15 16 17 18 $5000 19
20 21 22 23 24 25 $5000 26
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July 2027
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        1 2 $7500 3
4 5 6 7 8 9 $7500 10
11 12 13 14 15 16 $7500 17
18 19 20 21 22 23 $7500 24
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August 2027
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15 16 17 18 19 20 $7500 21
22 23 24 25 26 27 $7500 28
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Classic New England Cape in a quiet neighborhood, just a short distance to Vineyard Haven center. Enter through the front door into the nautical themed living space. With the well-equipped kitchen facing the dining and living areas even the cook will not miss visiting with family and friends. The primary bedroom with en suite bath at one end and
Vineyard Haven
$4,005.00 - $6,944.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Vineyard Haven 984
Classic New England Cape in a quiet neighborhood, just a short distance to Vineyard Haven center. Enter through the front door into the nautical them... Read More
June 2027
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    1 2 3 4 $4760 5
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13 14 15 16 17 18 $4760 19
20 21 22 23 24 25 $5775 26
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July 2027
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        1 2 $5775 3
4 5 6 7 8 9 $5180 10
11 12 13 14 15 16 $5180 17
18 19 20 21 22 23 $5906 24
25 26 27 28 29 30 $6944 31
August 2027
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1 2 3 4 5 6 $6944 7
8 9 10 11 12 13 $6944 14
15 16 17 18 19 20 $5600 21
22 23 24 25 26 27 $5600 28
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Step into this three-bedroom home and be greeted by water views that can be enjoyed from almost every room. Situated just across from the lagoon, this property is ideal for those who love paddle boarding and kayaking. Relax on the spacious deck, the perfect spot to enjoy your morning coffee, have a meal, or unwind with a good book. The main living
Vineyard Haven
$7,500.00 - $10,000.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Vineyard Haven 1275
Step into this three-bedroom home and be greeted by water views that can be enjoyed from almost every room. Situated just across from the lagoon, this... Read More
June 2027
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    1 2 3 4 $7500 5
6 7 8 9 10 11 $7500 12
13 14 15 16 17 18 $7500 19
20 21 22 23 24 25 $7500 26
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July 2027
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        1 2 $7500 3
4 5 6 7 8 9 $7500 10
11 12 13 14 15 16 $7500 17
18 19 20 21 22 23 $7500 24
25 26 27 28 29 30 $10000 31
August 2027
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1 2 3 4 5 6 $10000 7
8 9 10 11 12 13 $10000 14
15 16 17 18 19 20 $10000 21
22 23 24 25 26 27 $10000 28
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A stunning, contemporary design in Vineyard Haven with an abundance of sunlight and warmth throughout, this lovely four-bedroom home is perfect for so much more than a summer vacation. The grand living room features a stunning fireplace and double-height ceilings, which opens seamlessly into the gourmet kitchen with large center island. There are t
Vineyard Haven
$9,000.00 - $16,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Vineyard Haven 1221
A stunning, contemporary design in Vineyard Haven with an abundance of sunlight and warmth throughout, this lovely four-bedroom home is perfect for so... Read More
June 2027
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22 23 24 25 26 27 $16000 28
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Come relax in this newly renovated Vineyard Haven home, located just a short distance to downtown. The sunny kitchen evokes memories of days gone by but is roomy and efficient and has updated appliances. The kitchen opens into the dining area with a nice view onto the front porch. The front porch is where you will want to sit and watch the world go
Vineyard Haven
$3,000.00 - $7,500.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Vineyard Haven 912
Come relax in this newly renovated Vineyard Haven home, located just a short distance to downtown. The sunny kitchen evokes memories of days gone by b... Read More
June 2027
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    1 2 3 4 $5500 5
6 7 8 9 10 11 $5500 12
13 14 15 16 17 18 $5500 19
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July 2027
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        1 2 $6500 3
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August 2027
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8 9 10 11 12 13 $7500 14
15 16 17 18 19 20 $7500 21
22 23 24 25 26 27 $7500 28
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This spacious home is pristine and privately nestled in the woods of Lower Makonikey. It lives large with a spacious primary suite and three guest bedrooms, a fully equipped kitchen, butler's pantry, dining room, an office (in the event you need a private space to work while vacationing) and a light and airy family room which opens to a deck and th
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Vineyard Haven
$4,000.00 - $13,000.00 / per week
Beds 4 beds
Baths 4 Full Bath
Sleeps 8 sleeps
Vineyard Haven 1078
This spacious home is pristine and privately nestled in the woods of Lower Makonikey. It lives large with a spacious primary suite and three guest bed... Read More
June 2027
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    1 2 3 4 $5000 5
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        1 2 $5000 3
4 5 6 7 8 9 $5000 10
11 12 13 14 15 16 $5500 17
18 19 20 21 22 23 $6500 24
25 26 27 28 29 30 $7000 31
August 2027
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1 2 3 4 5 6 $11000 7
8 9 10 11 12 13 $13000 14
15 16 17 18 19 20 $10000 21
22 23 24 25 26 27 $6000 28
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