Vineyard Haven Rentals

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Make Vineyard Haven your next getaway—choose from 9 great vacation rentals

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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Vineyard Haven vacation rentals for every getaway

Dog-friendly Hot tub Internet
Sunset on the Vineyard 3D Tour
2 Bedroom | 1 Bath | Sleeps 4

Sunset on the Vineyard - Vineyard Haven, MA

From $250
The Vacation House 3D Tour
2 Bedroom | 1 Bath | Sleeps 6

The Vacation House - Vineyard Haven, MA

From $132
On Island Time 3D Tour
4 Bedroom | 2 Bath | Sleeps 8

On Island Time - Vineyard Haven, MA

From $150
Lily Hill 3D Tour
3 Bedroom | 2.5 Bath | Sleeps 6

Lily Hill - Vineyard Haven, MA

From $321
The CAVU Mansion on Bellevue 3D Tour
4 Bedroom | 5 Bath | Sleeps 8

The CAVU Mansion on Bellevue - Vineyard Haven, MA

From $307

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Recent Vineyard Haven vacation rental reviews

Fantastic space and location! Just a pleasant place for a relaxing getaway. Clean, well decorated with bright, cheerful and stylish decor. Its obviously set up to be a great summer spot, but even in winter, it shined. Nice and cozy spaces, tons of room. We were there with 5 adults and 4 kids with room to spare. There's everything you need to cook, but quick walk to Vineyard Haven downtown for coffee, takeout, supplies, etc. Planning to come back in the summer, can't wait to see it in season!
Ellen S. | Jan 2022
Perfect little getaway - not fancy but everything you need. Clean and cozy! Near the MV museum and a short walk to town. We loved our vacation here - thank you!
Jamie E. | Nov 2021
The cottage was pretty much as advertised but the kitchen pots and pans situation was pretty primitive, we don’t like to go out every Meal, and felt the kitchen eq was substandard. Also there was a coffee machine, and we’d done all our grocery shopping and arrived but then realized no coffee filters. The managing agent said they don’t provide those. Really? I’ve been to plenty of AirbNB that had olive oil and a few pantry items. Maybe because of COVID this is changed, but this annoyed us. Also there was a mega storm (nor’easter and power was out there as well as the whole town. Ferries we’re not running in either direction. In the am I asked since we could not leave the island if we could stay another night. They replied other guests were coming— which made no sense to us— . They said they could put us in another place, which was something but we didn’t want to move plus pay all the COVID cleaning fees again. (Fortunately for us our friends offered to squeeze us in.) Later in the day they said they would let us stay there one more night, that they didn’t understand all the ferries had stopped. Really? It was on the steamship authority site. Overall they were nice, but items mentioned here left us not thrilled.
Patricia S. | Nov 2021

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