Cheshire Vacation Rentals

Our Favorite Vacation Rentals in Cheshire

  • Berkshire Cottage
     Country House
    Booking.com
    From
    $695
  • Charming Berkshires lakefront house, great views
     2br Home/Apartment
    HolidayLettings
    From
    $348
  • Jiminy Peak Vacation Home
     Country House
    Booking.com
    From
    $800
  • Berkshires Waterfront Lakehouse Sanctuary
    Good3br Home/Apartment
    HolidayLettings
    From
    $310
  • Holiday Cottage
     Country House
    Booking.com
    From
    $500
  • Family Home w/ Game Room - 3 Miles to Jiminy Peak!
     4br Home/Apartment
    HolidayLettings
    From
    $581
  • Writers Cottage
     Country House
    Booking.com
    From
    $425
  • Sheeps Heaven View a stunning private suite in the Beautiful Berkshires
     3br Home/Apartment
    HolidayLettings
    From
    $208

Check prices for these upcoming dates

Cheshire Vacation Rentals with a Pool

  • Berkshire Gem - Ideal for Friends and Family
    Excellent4br Home/Apartment
    Airbnb
    From
    $791
  • Wyndham Bentley Brook * 2BR Deluxe
    Excellent2br Home/Apartment
    Airbnb
    From
    $388
  • Berkshire Cottage for 4 near Jiminy Peak
    Good2br Home/Apartment
    Airbnb
    From
    $219
  • 11-acre mid-century estate, newly renovated
    Good4br Home/Apartment
    Airbnb
    From
    $787

Cheshire Vacation Rentals with Wi-Fi

  • Ski @ our 19th c. Renovated Barn in the Berkshires
    Excellent3br Home/Apartment
    Airbnb
    From
    $345
  • Large Secluded Berkshire Home
    Good3br Home/Apartment
    Airbnb
    From
    $339
  • Cozy duplex with Mt. Greylock views
    Excellent2br Home/Apartment
    Airbnb
    From
    $119
  • Berkshire Gorge House/Williamstown
    Good5br Home/Apartment
    Airbnb
    From
    $305

Cheshire Pet-Friendly Vacation Rentals

  • Lake House w/ Deck & Views, Mins to Jiminy Peak!
     3br Cottage
    HolidayLettings
    From
    $695
  • 2200sf Country House on 16 Acres-2 Miles to Jiminy
    Good4br Home/Apartment
    HolidayLettings
    From
    $487
  • NEW! Hancock Log Home - 2Mi to Jiminy Peak Resort!
     3br Home/Apartment
    HolidayLettings
    From
    $421
  • Apartment walking distance to Mass MoCa!!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $249

Cheshire Travel Guide

Cheshire is a small community in Berkshire County with heaps of fun outdoor things to do, most notably the Ashuwillticook Rail Trail and the Appalachian Trail which goes right through the center of town, perfect for long hikes and bike rides.

Things to Do in Cheshire

The Ashuwillticook Rail Trail is a converted railroad, now a 10-foot wide paved trail very popular with hikers, cyclists, and runners. Watch out for scenic spots along the way, as the trail winds through woods, past lakes, and toward the Hoosac River. While en route, stop off at the popular local farm shop, Whitney's, in Cheshire and savor some well-deserved local produce.

There are also opportunities to hike, cycle, and run along the Appalachian Trail while watching for wildlife. This part of the trail takes visitors to Dalton from Cheshire and on a clear day, boasts picturesque views.

Best Time to Visit Cheshire

Visit during fall to see the colorful foliage.

Price and Availability in Cheshire

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

The Weather in Cheshire

Rainy days
58° -9°
3
59° -8°
2
67°
1
75° 20°
3
84° 34°
3
86° 37°
6
90° 49°
4
86° 42°
3
85° 33°
2
77° 29°
6
72° 10°
3
56° -4°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Cheshire. The warmest months in Cheshire are June and July, when temperatures reach 90 ˚F. The coolest month is December, when temperatures drop to -9 ˚F. The wettest month in Cheshire is July with 6.05 inches of rain, while the driest month is October with 1.05 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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