Chilmark Vacation Rentals

Our Favorite Vacation Rentals in Chilmark

  • Noah's Ark #6
     Home/Apartment
    Booking.com
    From
    $218
  • Stunning Private Vacation House With SkyLights in the Vineyard
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $364
  • New Listing! Magnificent Retreat On Deans Pond Home
     Country House
    Booking.com
    From
    $468
  • JUST LISTED! NEW & FABULOUS! THE BEECH HOUSE in LAMBERT'S COVE
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $665
  • Sea Glen Cottage
     Country House
    Booking.com
    From
    $132
  • Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town
    Excellent2br Home/Apartment
    Flipkey
    From
    $320
  • Stunning 3BD/2BA Vacation House in the Vineyard
     Country House
    Booking.com
    From
    $235
  • Gorgeous 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
    HolidayLettings
    From
    $396

Check prices for these upcoming dates

Chilmark Vacation Rentals with Wi-Fi

  • 4-Season Guest House on Historic Chilmark Estate
    ExcellentHome/Apartment
    Airbnb
    From
    $268
  • Charming Chilmark Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $283
  • Private, Beautiful Home in Chilmark Woods
    Good3br Home/Apartment
    Airbnb
    From
    $424
  • Oceanview Beachwalk Cottage
     Home/Apartment
    Airbnb
    From
    $339

Chilmark Pet-Friendly Vacation Rentals

  • Stunning 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
    HolidayLettings
    From
    $396
  • 1820s farmhouse SUITE with bath on 8 private acres
     Farmhouse
    Airbnb
    From
    $325
  • Catch n' Relax
     Home/Apartment
    Airbnb
    From
    $112
  • Vineyard Oasis
    Excellent5br Home/Apartment
    Airbnb
    From
    $735

Chilmark Travel Guide

The town of Chilmark is in the heart of Martha's Vineyard and is a great place for being at one with nature, or embarking along one of the best wine trails in the United States.

Things to Do in Chilmark

One of the best things to do in Chilmark is to participate in a tour or tasting of the many wineries and vineyards scattered throughout the area. Take a Martha's Vineyard tour, venture further afield to the Cape Cod Winery, or taste locally-brewed ales and hops at the Bad Martha Farmer's Brewery.

Best Time to Visit Chilmark

Chilmark is best visited during the warm summer months.

Price and Availability in Chilmark

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

The Weather in Chilmark

Rainy days
66° 15°
9
58° 13°
4
55°
4
54° 12°
8
63° 13°
5
66° 18°
4
83° 37°
2
86° 36°
3
91° 40°
2
92° 49°
1
88° 43°
3
78° 23°
6
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Chilmark. The hottest month in Chilmark is May, when temperatures peak at 92 ˚F. The coolest month is December, when temperatures drop to 1 ˚F. The wettest month in Chilmark 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 love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — 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

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