Vineyard Haven Vacation Rentals

Our Favorite Vacation Rentals in Vineyard Haven

  • Vineyard Artist's Haven
     Country House
  • Newly built in 2019! Lovely home w/ central AC, deck & gas grill!
     3br Home/Apartment
  • Barbara's Place
     Country House
  • Stunning Private Vacation House With SkyLights in the Vineyard
    Excellent3br Home/Apartment
  • Katama House
     Country House
  • Charming, dog-friendly home near beaches and marina!
    Excellent2br Home/Apartment
  • The Oak Estate
     Country House
  • Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town
    Excellent2br Home/Apartment

Check prices for these upcoming dates

Vineyard Haven Vacation Rentals with a Pool

  • Waterside Guest House
  • Two Ponds Residence
    Excellent8br Home/Apartment
  • Renovated picture perfect cape home on private lot
    Excellent3br Home/Apartment

Vineyard Haven Vacation Rentals with Wi-Fi

  • Lady Slipper Hill - Water View in the Woods
    Excellent4br Home/Apartment
  • Cozy Cottage
  • Charming Chilmark Cottage
  • Private, Beautiful Home in Chilmark Woods
    Good3br Home/Apartment

Vineyard Haven Pet-Friendly Vacation Rentals

  • 3 Bedroom in a great in-town location
     3br Home/Apartment
  • Gorgeous 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
  • Stunning 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
  • Newly built home w/ gourmet kitchen, furnished patio & grill - 1 dog OK!
     5br Home/Apartment

Vineyard Haven Travel Guide

Located within the small town of Tisbury, Vineyard Haven MA is a working village that boasts an inclusive community and diverse cultural values. With the ocean in such close proximity, Vineyard Haven rises each morning to the smell of the sea and sound of the seabirds, as well as the sun rising over the waters.

Things to Do in Vineyard Haven

Sitting atop the rocks of the Vineyard Haven Harbor, the Westchop lighthouse guides both sea captains and visitors to the small village of Vineyard Haven. Vineyard Haven visitors can spend the day outside at either Tisbury Town Beach, which offers views of incoming boats and a children’s playground, or Owen Park, which offers a great swimming spot and a low dock that can be used as a diving point. The Manuel F. Correllus State Forest in nearby Martha’s Vineyard is a quiet spot for biking, running, relaxing walks, rollerblading, and bird watching, as the many trails take visitors through the dense greenery and introduces them to friendly wildlife like squirrels and chipmunks. The Martha’s Vineyard Playhouse offers year-round theatrical performances by local actors and volunteers, while Martha’s Vineyard Tours and Excursions offers tours of Martha’s Vineyard island, lasting anywhere from 1-4 hours. Book lovers will be in heaven upon entering the Vineyard Haven Public Library as it houses a collection of books and the occasional art exhibit.

Best Places to Stay in Vineyard Haven

Vineyard Haven is a small town with strong beliefs in hospitality, so rental houses have popped up around the area. Many of the rentals are full houses offering dining areas, living rooms, en suites, and master bedrooms big enough to hold two king size beds and a group of your closest family and friends.

Best Time to Visit Vineyard Haven

The best time to visit is early September, as most of the summer tourists have gone home and the water is still warm enough to swim.

Food in Vineyard Haven

The food in Vineyard Haven is almost as diverse as the population, offering everything from quaint, all-American bakeries to Mediterranean restaurants. Blackdog Tavern offers a variety of seafood dishes and favorites like crab cakes, deep fried oysters, and quahog chowder. The Blackdog bakery and Little House Cafe serve homemade baked goods, and Little House Cafe is also known to serve juicy lamb burgers and seafood tacos that have been given a Mediterranean twist.

Best Events in Vineyard Haven

The annual Spectrum Film Festival -- a four day long celebration -- celebrates LGBT culture and rights. The event features guest speakers, discussions, films, and hosts a special event targeting LGBT youth and their supporters. The Tisbury Annual Street Fair and the Murdick’s 5 Mile Run the Chop Challenge are two other noteworthy events that take place each year.

Things to Do for Families in Vineyard Haven

The Vineyard Haven Cultural District is the perfect place for eager families who love to shop, as the district is home to a variety of one-of-a-kind shops and boutiques that are all conveniently lined up along Main Street.

Price and Availability in Vineyard Haven

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The cheapest day to stay at a vacation rental in Vineyard Haven tends to be Sunday, while the most expensive day tends to be Friday. Vacation homes in Vineyard Haven tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Vineyard Haven is in August, while the cheapest month is in October. The most popular time to book a vacation rental in Vineyard Haven is in the high season in August. Vineyard Haven has its low season in November, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Vineyard Haven

Rainy days
66° 15°
58° 13°
54° 12°
63° 13°
66° 18°
86° 36°
91° 40°
92° 49°
88° 43°
78° 23°
Rainy days

This climate histogram shows you the weather patterns in Vineyard Haven. The warmest months in Vineyard Haven are May and June, when temperatures reach 92 ˚F. The coolest month is August, when temperatures drop to 1 ˚F. The wettest month in Vineyard Haven is February with 9.01 inches of rain, while the driest month is May with 1.25 inches of rain.

What Expert Travelers Think

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    Kacie MorganThe Rare Welsh Bit
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    Whitney WearTravel Better Guide

Vacation Rentals in Vineyard Haven

Browse accommodations from all your favorite providers including Airbnb, RedAwning, Hostelworld and others at We have 393 vacation rentals, hotels and other places to stay in Vineyard Haven ranging from low-cost options to luxury places to stay. A trip to Vineyard Haven can be affordable - our cheapest price vacation rental is available at $40 a night. On average, an accommodation in Vineyard Haven will cost you $537 per night.

If you want to stay connected during your vacation, then you can choose from over 157 accommodations in Vineyard Haven that have WiFi. 14 of our accommodations come with breakfast in the price. Driving to Vineyard Haven? Then choose one of the 165 places to stay that comes with a parking spot included. 9 hotels and vacation rentals have a a pool or jacuzzi

If you're traveling with your best friend, then make sure to select one of the 46 pet-friendly accommodations available.

243 of our places to stay in Vineyard Haven have been rated by previous guests. They rated 69% as excellent or good. 105 accommodations allow instant booking.

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