Vineyard Haven Rentals

Compare 11 vacation rentals. Enter your trip dates to get started.
USA > Massachusetts > Vineyard Haven

Make Vineyard Haven your next getaway—choose from 11 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. 

Explore Vineyard Haven house rentals, cottages, and more


House rentals

View 10 House rentals


View 1 Cottages

Vineyard Haven vacation rentals for every getaway

Dog-friendly Hot tub Internet
The Vacation House 3D Tour
2 Bed | 1 Bath | Sleeps 6

The Vacation House - Vineyard Haven, MA

From $130
The CAVU Mansion on Bellevue 3D Tour
4 Bed | 5 Bath | Sleeps 8

The CAVU Mansion on Bellevue - Vineyard Haven, MA

From $298
Islander's Retreat 3D Tour
3 Bed | 3.5 Bath | Sleeps 9

Islander's Retreat - Vineyard Haven, MA

From $320
Vineyard Artist's Haven 3D Tour
4 Bed | 3 Bath | Sleeps 8

Vineyard Artist's Haven - Vineyard Haven, MA

From $300
The Vineyard Retreat 3D Tour
3 Bed | 2 Bath | Sleeps 6

The Vineyard Retreat - Vineyard Haven, MA

From $350

View 6 more homes

Recent Vineyard Haven vacation rental reviews

Beautiful yard, plenty of space
Jessica S. | Aug 2021
Spacious house with 3 bathrooms made our stay effortless. Very quiet and a nice retreat for our group.
Rhonda D. | Aug 2021
Thank you to the Jones for sharing their beautiful home! We thoroughly enjoyed our family vacation here with plenty of space to fit two families and several teens/kids. Location was ideal for biking into Vineyard Haven, running/biking in the area (Lake Tashmoo is a hidden gem), and day trips to other areas of the island. The house was spacious and beautifully decorated with gorgeous artwork. Appreciated the air conditioners and ample fans in each room!
Audrey C. | Aug 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