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 59 properties available
Water, water, everywhere! Enjoy this delightful waterfront cottage perfectly situated between Vineyard Sound and Lake Tashmoo, offering beautiful water views from both the front and back. This single-level, two-bedroom home is the ideal island escape—simple, peaceful, and surrounded by nature. Relax on the back deck, rinse off in the outdoor shower
Vineyard Haven
$4,043.00 - $7,090.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Vineyard Haven 1250
Water, water, everywhere! Enjoy this delightful waterfront cottage perfectly situated between Vineyard Sound and Lake Tashmoo, offering beautiful wate... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $5530 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 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Gracious West Chop home and guest house ready for your perfect Vineyard vacation. On the approach you feel like you are visiting a West Chop home of days gone by, but once you open the door, you see otherwise! The carefully curated decor creates a comfortable yet elegant space and every detail has been tended to. The open first floor living area al
Vineyard Haven
$11,000.00 - $14,000.00 / per week
Beds 7 beds
Baths 7 Full, 1 Half Bath
Sleeps 14 sleeps
Vineyard Haven 1256
Gracious West Chop home and guest house ready for your perfect Vineyard vacation. On the approach you feel like you are visiting a West Chop home of d... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $11000 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 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

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 - $6,804.00 / 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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $4501 6
7 8 9 10 11 12 $4501 13
14 15 16 17 18 19 $4501 20
21 22 23 24 25 26 $4501 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 $4949 4
5 6 7 8 9 10 $4949 11
12 13 14 15 16 17 $4515 18
19 20 21 22 23 24 $5250 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            $5250 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 $6804 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $1900 6
7 8 9 10 11 12 $1900 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

This very well maintained single level home is perfectly situated on a quiet street between Main Street and the lulling waves of West Chop, and roughly a quarter-mile to downtown Vineyard Haven. Offering three bedrooms, two and a half baths, central air as well as a large kitchen with a large center island and a multitude of cookware and countertop
Vineyard Haven
$5,400.00 - $6,000.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Rating 5 (1)
Vineyard Haven 1237
This very well maintained single level home is perfectly situated on a quiet street between Main Street and the lulling waves of West Chop, and roughl... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $5400 6
7 8 9 10 11 12 $5600 13
14 15 16 17 18 19 $5600 20
21 22 23 24 25 26 $5600 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 $5700 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 $5900 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

This sweet cottage in Vineyard Haven offers a partial view across the Lagoon toward the Sound and bridge. Take advantage of the expansive deck facing the water to enjoy breezy summer days and evenings admiring the sunsets. Freshly updated home with open living space, dining area and adjacent wet bar with the kitchen beyond. Also on the first floor
Vineyard Haven
$4,000.00 - $7,000.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 6 sleeps
Vineyard Haven 1243
This sweet cottage in Vineyard Haven offers a partial view across the Lagoon toward the Sound and bridge. Take advantage of the expansive deck facing ... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $4000 6
7 8 9 10 11 12 $4000 13
14 15 16 17 18 19 $4000 20
21 22 23 24 25 26 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 $4000 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Enjoy the salty air as you unpack the car and settle in to this one month minimum stay rental. Mornings can be spent making coffee and watching the boats cascade through the outer harbor, play in the gentle waves - and the Steamship continue it's trek, back and forth. Nestled between downtown Vineyard Haven and on the cusp of West Chop, this three-
Vineyard Haven Pet Friendly
$6,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Vineyard Haven 1215
Enjoy the salty air as you unpack the car and settle in to this one month minimum stay rental. Mornings can be spent making coffee and watching the bo... Read More
June 2026
Su Mo Tu We Th Fr Sa
  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 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Sweet cottage on a quiet street in Vineyard Haven. Tastefully renovated, this modern home maintains the charm of a Vineyard cottage. Brand new kitchen and all new furnishings make this a comfortable getaway for up to four guests. One story with two bedrooms that share a bath, and of course an enclosed outdoor shower. Enjoy a good book on the lovel
🚢Ferry Tickets
🚢Ferry Tickets
July 3rd - July 10th
Vineyard Haven
$2,000.00 - $3,500.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Rating 5 (2)
Vineyard Haven 1248
Sweet cottage on a quiet street in Vineyard Haven. Tastefully renovated, this modern home maintains the charm of a Vineyard cottage. Brand new kitchen... Read More
June 2026
Su Mo Tu We Th Fr Sa
  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 $3000 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 $3000 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Step into your next island getaway at this beautifully remodeled 5 bedroom Vineyard Haven home, thoughtfully designed for comfort, style and entertaining. The first floor offers living and dining space and a sparkling white kitchen with stainless appliances. The first of five bedrooms is also on the first floor with an en suite. Upstairs are 3 addi
Vineyard Haven
$8,500.00 - $18,000.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Vineyard Haven 1274
Step into your next island getaway at this beautifully remodeled 5 bedroom Vineyard Haven home, thoughtfully designed for comfort, style and entertain... Read More
June 2026
Su Mo Tu We Th Fr Sa
  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 $8500 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 $14500 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 31  
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 $18000 22
23 24 25 26 27 28 $18000 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Looking for a cozy get away? Then this one bedroom in town Vineyard Haven guest house is waiting for you. Inside you will find a tastefully and beautifully decorated queen bedded room with a hall bathroom, a fully equipped kitchen and comfortable living area. It has window air conditioning units for those warm days to keep you cool. Plenty of off s
Vineyard Haven
$4,550.00 - $5,600.00 / per week
Beds 1 beds
Baths 1 Full Bath
Sleeps 2 sleeps
Rating 5 (1)
Vineyard Haven 986
Looking for a cozy get away? Then this one bedroom in town Vineyard Haven guest house is waiting for you. Inside you will find a tastefully and beauti... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $4550 6
7 8 9 10 11 12 $4550 13
14 15 16 17 18 19 $4550 20
21 22 23 24 25 26 $5600 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 $5600 4
5 6 7 8 9 10 $5600 11
12 13 14 15 16 17 $5600 18
19 20 21 22 23 24 $5600 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 $5600 15
16 17 18 19 20 21 $5600 22
23 24 25 26 27 28 $5600 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Nestled in the heart of Vineyard Haven, this charming three-bedroom property offers the perfect blend of tranquility and convenience. Situated in the neighborhood of scenic Mink Meadows Golf Course and Mink Meadows Association Beach, you'll experience the best of both relaxation and recreation. On the first floor you'll find plenty of living spaces
🚢Ferry Tickets
🚢Ferry Tickets
July 3rd - July 10th, August 21st - September 4th
Vineyard Haven Pet Friendly
$3,000.00 - $7,500.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 9 sleeps
Vineyard Haven 1266
Nestled in the heart of Vineyard Haven, this charming three-bedroom property offers the perfect blend of tranquility and convenience. Situated in the ... Read More
June 2026
Su Mo Tu We Th Fr Sa
  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 $7000 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      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 31  
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 $7500 22
23 24 25 26 27 28 $7500 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
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 2026
Su Mo Tu We Th Fr Sa
  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 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 $11000 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            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 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Tell us what you're looking for and someone will contact you with available options.

I agree