Chilmark Vacation Rentals

Our Favorite Vacation Rentals in Chilmark

  • Stunning 3BD/2BA Vacation House in the Vineyard
     Country House
    Booking.com
    From
    $233
  • Newly built in 2019! Lovely home w/ central AC, deck & gas grill!
     3br Home/Apartment
    HolidayLettings
    From
    $351
  • NEW & FABULOUS! WALK TO LAMBERT'S COVE BEACH & ICE HOUSE POND
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $665
  • Beautiful, Updated, Well-Appointed Home ~ 3bdrm, 4bth in Ideal Private Location
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $553
  • Charming, dog-friendly home near beaches and marina!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $297
  • Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town
    Excellent2br Home/Apartment
    Flipkey
    From
    $320
  • Stunning Private Vacation House With SkyLights in the Vineyard
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $361
  • Gorgeous 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
    HolidayLettings
    From
    $394

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
  • Private, Beautiful Home in Chilmark Woods
    Good3br Home/Apartment
    Airbnb
    From
    $424
  • Oceanview Beachwalk Cottage
     Home/Apartment
    Airbnb
    From
    $311
  • Martha's Vineyard Oceanview Retreat
    Excellent3br Home/Apartment
    Airbnb
    From
    $486

Chilmark Pet-Friendly Vacation Rentals

  • Stunning 3BD/2BA Vacation House in the Vineyard
     4br Home/Apartment
    HolidayLettings
    From
    $394
  • Private West Tisbury Loft with trail/beach access
    GoodHome/Apartment
    Airbnb
    From
    $240
  • Vineyard Oasis
    Excellent5br Home/Apartment
    Airbnb
    From
    $961
  • Newly built in 2019! Lovely home w/ central AC, deck & gas grill!
     3br Home/Apartment
    Airbnb
    From
    $495

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
56°
5
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
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Chilmark. The warmest months in Chilmark are June and May, when temperatures reach 92 ˚F. The coolest month is November, when temperatures drop to 2 ˚F. The wettest month in Chilmark 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 love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy

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