Vineyard Haven Rentals

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Make Vineyard Haven your next getaway

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. 

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House rentals

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Vineyard Haven vacation rentals for every getaway

Dog-friendly Hot tub Internet
Main Street Upper
2 Bedroom | 2 Bath | Sleeps 7

Main Street Upper - Vineyard Haven, MA

$290 avg / night
Island Time
1 Bedroom | 1 Bath | Sleeps 4

Island Time - Vineyard Haven, MA

$251 avg / night
Lily Hill
3 Bedroom | 2.5 Bath | Sleeps 6

Lily Hill - Vineyard Haven, MA

$705 avg / night
The CAVU Mansion on Bellevue
4 Bedroom | 5 Bath | Sleeps 8

The CAVU Mansion on Bellevue - Vineyard Haven, MA

$505 avg / night
Everyday is Saturday
3 Bedroom | 1 Bath | Sleeps 6

Everyday is Saturday - Vineyard Haven, MA

$342 avg / night

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Recent Vineyard Haven vacation rental reviews

Perfect for what we needed
Danielle f. | Apr 2024
We had a wonderful stay. The hosts had everything we could need including lots of helpful suggestions. Very clean, spacious, just very comfortable & cozy, comfortable beds, kitchen essentials provided, great location, they really thought of everything we could need. I would definitely stay again.
Mark u. | Mar 2024
Great location, plenty of room. Very clean.
Darryl S. | Jan 2024
Vineyard Haven vacation rental FAQ

Yes, 67 of our Vineyard Haven homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 219 of our Vineyard Haven vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Vineyard Haven vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Vineyard Haven team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Vineyard Haven, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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