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Vineyard Haven Vacation Rentals

1 - 42 of 42 rentals
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Nature's Pocket  - Vineyard Haven, MA Vacation Rental

Nature's Pocket

Vineyard Haven, MA
3 Bed 3 Bath Sleeps 6
270 270 320 320 290 290 290 290 290 340 340 290 290 290 290 290 340
The Happy Place  - Vineyard Haven, MA Vacation Rental

The Happy Place

Vineyard Haven, MA
4 Bed 1.5 Bath Sleeps 8
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Seventh Heaven  - Vineyard Haven, MA Vacation Rental

Seventh Heaven

Vineyard Haven, MA
4 Bed 2 Bath Sleeps 9
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Lantern Lane - Vineyard Haven, MA Vacation Rental

Lantern Lane

Vineyard Haven, MA
4 Bed 2.5 Bath Sleeps 11
185 185 235 235 195 195 195 195 195 250 250 195 195 195 195 195 250
The Vacation House - Vineyard Haven, MA Vacation Rental

The Vacation House

Vineyard Haven, MA
2 Bed 1 Bath Sleeps 6
99 99 145 145 115 115 115 115 115 155 155 115 115 115 115 115 155
Islander's Retreat  - Vineyard Haven, MA Vacation Rental

Islander's Retreat

Vineyard Haven, MA
3 Bed 3.5 Bath Sleeps 9
285 285 320 320 295 295 295 295 295 340 340 295 295 295 295 295 340
The Looks Pond Garden House - West Tisbury, MA Vacation Rental
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Tranquility on Great Plains - West Tisbury, MA Vacation Rental
160 160 195 195 170 170 170 170 170 220 220 170 170 170 170 170 220
Bright Grove - Oak Bluffs, MA Vacation Rental

Bright Grove

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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Oak Villa - Edgartown, MA Vacation Rental

Oak Villa

Edgartown, MA
6 Bed 3.5 Bath Sleeps 13
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The CAVU Mansion on Bellevue  - Tisbury, MA Vacation Rental
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Pine Street Haven - Edgartown, MA Vacation Rental

Pine Street Haven

Edgartown, MA
4 Bed 3 Bath Sleeps 8
140 130 - - - - - - - 215 225 160 160 160 160 160 225
The Walker House  - Oak Bluffs, MA Vacation Rental

The Walker House

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Cape on Forest  - Oak Bluffs, MA Vacation Rental

Cape on Forest

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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The Blue Cape - Edgartown, MA Vacation Rental

The Blue Cape

Edgartown, MA
3 Bed 2 Bath Sleeps 8
120 120 180 180 125 125 125 135 135 195 195 135 135 135 135 135 195
Casita del Amor "Love Cottage" - Edgartown, MA Vacation Rental
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Colonial Blue on Whalers Walk - Edgartown, MA Vacation Rental
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The Wayland Victorian - Oak Bluffs, MA Vacation Rental

The Wayland Victorian

Oak Bluffs, MA
5 Bed 2 Bath Sleeps 12
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Island Sanctuary - Oak Bluffs, MA Vacation Rental

Island Sanctuary

Oak Bluffs, MA
3 Bed 1.5 Bath Sleeps 7
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Oak View Cottage  - Oak Bluffs, MA Vacation Rental

Oak View Cottage

Oak Bluffs, MA
3 Bed 2.5 Bath Sleeps 6
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Briar Patch - Edgartown, MA Vacation Rental

Briar Patch

Edgartown, MA
3 Bed 2 Bath Sleeps 7
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Serenity  - Oak Bluffs, MA Vacation Rental

Serenity

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 4
125 125 155 155 130 130 130 130 130 165 165 130 130 130 130 130 165
The Samoset  - Oak Bluffs, MA Vacation Rental

The Samoset

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Casa de Reyna - Edgartown, MA Vacation Rental

Casa de Reyna

Edgartown, MA
5 Bed 3.5 Bath Sleeps 8
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Sunset Meadows - Oak Bluffs, MA Vacation Rental

Sunset Meadows

Oak Bluffs, MA
2 Bed 1 Bath Sleeps 4
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The  Eliot Noyes - Chilmark, MA Vacation Rental

The Eliot Noyes

Chilmark, MA
4 Bed 2 Bath Sleeps 8
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Sweet Island Child - Chilmark, MA Vacation Rental

Sweet Island Child

Chilmark, MA
3 Bed 2 Bath Sleeps 6
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Martha's Nest - Edgartown, MA Vacation Rental

Martha's Nest

Edgartown, MA
3 Bed 2 Bath Sleeps 8
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The Bird's Nest  - Chilmark, MA Vacation Rental

The Bird's Nest

Chilmark, MA
2 Bed 1 Bath Sleeps 4
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Off the Radar on Hidden Village Road - West Tisbury, MA Vacation Rental
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Island Romance  - Chilmark, MA Vacation Rental

Island Romance

Chilmark, MA
4 Bed 1.5 Bath Sleeps 8
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Captain's Cottage - Falmouth, MA Vacation Rental

Captain's Cottage

Falmouth, MA
1 Bed 1 Bath Sleeps 5
99 99 150 150 115 115 115 160 160 195 195 160 160 160 160 160 195
The Green Monstah! - Falmouth, MA Vacation Rental

The Green Monstah!

Falmouth, MA
4 Bed 1.5 Bath Sleeps 12
220 220 255 255 235 235 235 185 185 235 235 185 185 185 185 185 235
Beauty and the Beach on Chapoquoit Island  - Falmouth, MA Vacation Rental
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Stunning Coastal Retreat - Falmouth, MA Vacation Rental

Stunning Coastal Retreat

Falmouth, MA
5 Bed 2.5 Bath Sleeps 12
140 140 175 175 145 155 155 160 160 225 215 - - - - - -
"Old Silver" - Falmouth, MA Vacation Rental

"Old Silver"

Falmouth, MA
2 Bed 1 Bath Sleeps 4
130 130 170 170 135 135 135 160 160 195 195 160 160 160 160 160 195
Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
215 215 245 245 225 225 225 175 175 225 225 175 175 175 175 175 225
Mill View: La Maison de l'Artiste - Falmouth, MA Vacation Rental
130 130 170 170 135 135 135 135 135 180 180 135 135 135 135 135 180
Historic Whaling Captain's Home - Falmouth, MA Vacation Rental
700 700 700 700 700 700 700 700 700 700 700 700 700 700 700 700 700
Historic Whaling Captain's Home & Cottage - Falmouth, MA Vacation Rental
750 750 750 750 750 750 750 750 750 750 750 750 750 750 750 750 750
A Slice of Heaven in Falmouth - Falmouth, MA Vacation Rental
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Toes In The Sand at Craigville Beach - Centerville , MA Vacation Rental
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About Vineyard Haven

Vineyard Haven rated 4.7 out of 5 based on 43 reviews Vineyard haven, MA

A lovely historic harbor. Pristine red brick streets. Cozy, sandy beaches. Bustling mom-and-pop shops. They all get top billing in Vineyard Haven, Massachusetts. A stay at one of our Vineyard Haven vacation rentals is sure to please anyone heading to Martha's Vineyard, whatever the season. 

Vineyard Haven, commonly known as Tisbury, is a mecca for tourists. English settlers first arrived in the mid-1600s and additional mainlanders flocked to this sleepy seaside community soon after. The town, once known as Holmes Hole, thrived thanks to its easily accessible harbor. Today, Vineyard Haven is replete with cute shops, lovely parks, and historic sites of note. Come stay at one of our Vineyard Haven cottages and you'll see why the town is one of the most picturesque in all of Massachusetts.  

Things To Do in Vineyard Haven

Old Schoolhouse Museum, built in 1828, has had many incarnations: a carpentry shop, school, and church, but is most visited for the Liberty Pole out front. This site commemorates the service of three local women who helped foil the British navy during the Revolutionary War. 

The Martha's Vineyard Playhouse, erected in 1833, was once a Methodist meeting house and is now home to the town's theater company. Head here for outdoor performances in the summer and Shakespearean plays the rest of the year. 

The West Chop Lighthouse, situated on the harbor, is a 45-foot stone and brick lighthouse built in 1891. You can't go inside but great pictures can be had from the parkland outside. 

Vineyard Haven Outdoor Attractions 

Our Vineyard Haven vacation rentals are near a wealth of outdoor attractions for the entire family. As it sits on a harbor, the beach is the main draw and visitors have access to three public beaches. Lake Tashmoo Town Beach is quiet and affords places to fish. You can watch the ships sail by at popular Owen Park Beach near the harbor. Tisbury Town Beach is a great spot to swim but is only accessible by foot or bike. 

A variety of green spaces are on hand for your enjoyment. The Long Point Wildlife Refuge boasts more than 600 acres of beach, dune, woodland, and heath and is a haven for birdwatchers and nature lovers. War Veteran's Memorial Park is great for kids as it has a playground and ballpark. Owen Park, Lake Street Park, and Hagerty Park are small but great spots to while away the hours before you get ready for dinner. Tashmoo Lake Overlook is also special because of its glorious views of the island.

Day Trips from Vineyard Haven

Vineyard Haven is centrally located on Martha's Vineyard, making it a fine spot to base a day trip around the island. Head to the 60-acre Polly Hill Arboretum in West Tisbury, which is only seven miles away. Edgartown boasts the expansive Cape Pogue Wildlife Refuge and the Felix Neck Wildlife Sanctuary. Head to Oaks Bluff for the oldest carousel in the nation as well as a few museums, an art center, and the East Chop Lighthouse. 

Stroll the quaint shops, converse with friendly locals, or relax on the beach. Whatever your pleasure, our Vineyard Haven vacation rentals will help you find it.

Photo credit: Amy Meredith via Flickr

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