Chilmark Vacation Rentals

Our Favorite Vacation Rentals in Chilmark

  • New Listing! Magnificent Retreat on Deans Pond
     3br Home/Apartment
    RedAwning
    From
    $837
  • Dream on the Beach
     Country House
    Booking.com
    From
    $619
  • Cozy lakefront home w/ gorgeous lake views & bikes available!
     4br Home/Apartment
    HolidayLettings
    From
    $668
  • Sea Glen Cottage
     Country House
    Booking.com
    From
    $217
  • JUST LISTED! NEW & FABULOUS! THE BEECH HOUSE in LAMBERT'S COVE
     3br Home/Apartment
    HolidayLettings
    From
    $678
  • #OB Pool House
     Country House
    Booking.com
    From
    $728
  • Bright & airy modern 3-level home near the beach and downtown
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $526
  • The Mermaid Suite
    GoodCountry House
    Booking.com
    From
    $125

Check prices for these upcoming dates

Chilmark Vacation Rentals with a Pool

  • NEW LISTING! Luxury home w/pool & foosball-near 3 towns & many beaches
    Good5br Home/Apartment
    Airbnb
    From
    $1,014

Chilmark Vacation Rentals with Wi-Fi

  • Beautiful Guest House in Chilmark
    ExcellentHome/Apartment
    Airbnb
    From
    $283
  • Beautifully Renovated 1800s Chilmark Barn
    Excellent2br Home/Apartment
    Airbnb
    From
    $273
  • Charming Chilmark Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $283
  • Private, Beautiful Home in Chilmark Woods
    Good3br Home/Apartment
    Airbnb
    From
    $424

Chilmark Pet-Friendly Vacation Rentals

  • Charming, dog-friendly home near beaches and marina!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $365
  • Ferry Tix, Chilmark, South of South Rd, 4bd/4bth,
    Excellent4br Home/Apartment
    Airbnb
    From
    $593
  • Sweet 3BR Cape in West Tisbury, MV
    Excellent3br Home/Apartment
    Airbnb
    From
    $269
  • Oceanfront home w/deck, amazing sunset views & beach access-dogs OK
     4br Home/Apartment
    Airbnb
    From
    $938

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
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 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
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — 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

    Whitney Wear
    Whitney WearTravel Better Guide

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