Vineyard Haven Vacation Rentals

Our Favorite Vacation Rentals in Vineyard Haven

  • Falmouth Family Getaway
     4br Home/Apartment
    RedAwning
    From
    $536
  • Noah's Ark #6
     Home/Apartment
    Booking.com
    From
    $175
  • Newly built in 2019! Lovely home w/ central AC, deck & gas grill!
     3br Home/Apartment
    HolidayLettings
    From
    $419
  • Beachside Retreat - 300 Yards to Surf Drive Shore
     3br Home/Apartment
    RedAwning
    From
    $560
  • Beach Edgartown Center Restaurantes Bar Bike Path
     Home/Apartment
    Booking.com
    From
    $139
  • Stunning Private Vacation House With SkyLights in the Vineyard
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $429
  • The Oak Estate
     Country House
    Booking.com
    From
    $433
  • NEW & FABULOUS! WALK TO LAMBERT'S COVE BEACH & ICE HOUSE POND
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $537

Check prices for these upcoming dates

Vineyard Haven Vacation Rentals with a Pool

  • Two Ponds Residence
    Excellent8br Home/Apartment
    Airbnb
    From
    $735

Vineyard Haven Vacation Rentals with Wi-Fi

  • MV Private Cottage-- renovated, sunny, private
    ExcellentCottage
    Airbnb
    From
    $182
  • Lady Slipper Hill - Water View in the Woods
    Excellent4br Home/Apartment
    Airbnb
    From
    $537
  • New Chilmark Gem
    ExcellentHome/Apartment
    Airbnb
    From
    $283
  • Renovated barn near Great Pond, WT
    Excellent2br Home/Apartment
    Airbnb
    From
    $452

Vineyard Haven Pet-Friendly Vacation Rentals

  • Charming, dog-friendly home near beaches and marina!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $277
  • Clean, comfortable ranch with lots of amenities
     3br Home/Apartment
    HolidayLettings
    From
    $703
  • Charming Martha's Vineyard Home Near Beach & Town!
     2br Home/Apartment
    HolidayLettings
    From
    $401
  • Gorgeous 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
    HolidayLettings
    From
    $462

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

Most expensive
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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
62°
2
59°
4
70° 14°
4
77° 31°
4
83° 39°
6
92° 50°
3
86° 44°
3
80° 36°
3
80° 30°
7
69° 13°
3
59° 10°
7
56°
5
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Vineyard Haven. The warmest months in Vineyard Haven are June and May, when temperatures reach 92 ˚F. The coolest month is November, when temperatures drop to 2 ˚F. The wettest month in Vineyard Haven is January with 7.37 inches of rain, while the driest month is November with 2.36 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

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  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

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    Whitney WearTravel Better Guide
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

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Vacation Rentals in Vineyard Haven

At AllTheRooms.com we have vacation rentals from all of your favorite providers - Airbnb, Priceline, RedAwning and more. AllTheRooms has 393 rentals, hotels and other great places to stay during your time in Vineyard Haven, with everything from inexpensive hostels and homestays to extravagant Airbnbs and hotels. For those trying to keep costs down, the lowest priced place to stay in Vineyard Haven comes in at $38 a night. On average, a place to stay in Vineyard Haven will cost you $544 per night.

If you want to stay connected during your vacation, then you can choose from over 155 accommodations in Vineyard Haven that have WiFi. We have 12 accommodations that include a breakfast included. If you're planning on getting to Vineyard Haven by car, be sure to choose from 158 accommodations that provide parking. 9 vacation rentals have a a pool or jacuzzi

If you're traveling with a furry friend, then be sure to select one of the 42 pet-friendly accommodations available.

236 of the places to stay in Vineyard Haven have been rated by previous guests. They rated 67% as great. 113 accommodations allow instant booking.

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