Vineyard Haven Vacation Rentals

Our Favorite Vacation Rentals in Vineyard Haven

  • New Listing! Magnificent Retreat on Deans Pond
     3br Home/Apartment
    RedAwning
    From
    $959
  • Sea Glen Cottage
     Country House
    Booking.com
    From
    $212
  • Cozy lakefront home w/ gorgeous lake views & bikes available!
     4br Home/Apartment
    HolidayLettings
    From
    $668
  • Falmouth Family Getaway
     4br Home/Apartment
    RedAwning
    From
    $769
  • #OB Pool House
     Country House
    Booking.com
    From
    $713
  • JUST LISTED! NEW & FABULOUS! THE BEECH HOUSE in LAMBERT'S COVE
     3br Home/Apartment
    HolidayLettings
    From
    $678
  • New Listing! Beachside Retreat - 300 Yards to Shore
     3br Home/Apartment
    RedAwning
    From
    $643
  • The Bluffs Estate
     Country House
    Booking.com
    From
    $406

Check prices for these upcoming dates

Vineyard Haven Vacation Rentals with a Pool

  • Renovated picture perfect cape home on private lot
    Excellent3br Home/Apartment
    Airbnb
    From
    $579
  • Two Ponds Residence
    Excellent8br Home/Apartment
    Airbnb
    From
    $735

Vineyard Haven Vacation Rentals with Wi-Fi

  • Summercamp
    Good95br 3-star Home/Apartment
    Booking.com
    From
    $169
  • Sweet Spot in Heart of West Tisbury
    Excellent3br Home/Apartment
    Airbnb
    From
    $565
  • Ferry Tix, Chilmark, South of South Rd, 4bd/4bth,
    Excellent4br Home/Apartment
    Airbnb
    From
    $593
  • MV Private Cottage-- renovated, sunny, private
    ExcellentCottage
    Airbnb
    From
    $240

Vineyard Haven Pet-Friendly Vacation Rentals

  • Charming, dog-friendly home near beaches and marina!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $370
  • Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $3,130
  • 3 Bedroom in a great in-town location
     3br Home/Apartment
    HolidayLettings
    From
    $518
  • Classic, private estate with a large lot, a stone patio & a fireplace!
     3br Home/Apartment
    HolidayLettings
    From
    $701

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
88 º43
3
78 º23
6
66 º15
9
58 º13
4
55 º1
4
54 º12
8
63 º13
5
66 º18
4
83 º37
2
86 º36
3
91 º40
2
92 º49
1
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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 December, 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

  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

Vacation Rentals in Vineyard Haven

Browse vacation rentals from all the leading providers including Airbnb, RedAwning, Hostelworld and more at AllTheRooms.com. We have 384 vacation rentals, hotels and other accommodation types in Vineyard Haven ranging from low-cost options to luxury places to stay. For those traveling on a budget, the most economical place to stay in Vineyard Haven is available at $38 per night. The average price of a rental is $537 per night.

Those looking to get some work finished during their trip to Vineyard Haven can pick from 223 places to stay that provide WiFi. 13 of our accommodations come with breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 5 accommodations that have gym facilities. If you're planning on arriving in Vineyard Haven by car, be sure to choose from 227 accommodations that provide parking. We track 9 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 65 pet-friendly places to stay in Vineyard Haven, so if you're traveling with your pet you won't have any problems.

238 of the places to stay in Vineyard Haven have been reviewed by previous guests. They rated 69% as excellent or good. You can instantly book any of 102 places to stay right now.

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