Cheshire Vacation Rentals

Our Favorite Vacation Rentals in Cheshire

  • Tentrr - Birch Berry Pines
     Country House
    Booking.com
    From
    $144
  • Charming Berkshires lakefront house, great views
     2br Home/Apartment
    HolidayLettings
    From
    $348
  • Berkshire Cottage
     Country House
    Booking.com
    From
    $700
  • Berkshires Waterfront Lakehouse Sanctuary
    Good3br Home/Apartment
    HolidayLettings
    From
    $310
  • Jiminy Peak Vacation Home
     Country House
    Booking.com
    From
    $1,050
  • Family Home w/ Game Room - 3 Miles to Jiminy Peak!
     4br Home/Apartment
    HolidayLettings
    From
    $524
  • Heart Of The Berkshires
     Home/Apartment
    Booking.com
    From
    $155
  • New England Style 2BR Suite at Vacation Village in the Berkshire
     2br Home/Apartment
    HolidayLettings
    From
    $205

Check prices for these upcoming dates

Cheshire Vacation Rentals with a Pool

  • Sunny S. Williamstown Loft with Stunning Views
    ExcellentStudio
    Airbnb
    From
    $147
  • Berkshire Cottage for 4 near Jiminy Peak
    Good2br Home/Apartment
    Airbnb
    From
    $242
  • 11-acre mid-century estate, newly renovated
    Excellent4br Home/Apartment
    Airbnb
    From
    $787
  • Amazing, Spacious Estate on 10 Acres
    Excellent8br Estate
    Airbnb
    From
    $1,732

Cheshire Vacation Rentals with Wi-Fi

  • 19th c. Renovated Barn in the Berkshires
    Excellent3br Home/Apartment
    Airbnb
    From
    $345
  • Stone School Cottage
    Excellent2br Home/Apartment
    Airbnb
    From
    $186
  • Large Secluded Berkshire Home
    Good3br Home/Apartment
    Airbnb
    From
    $367
  • Cozy duplex with Mt. Greylock views
    Excellent2br Home/Apartment
    Airbnb
    From
    $119

Cheshire Pet-Friendly Vacation Rentals

  • 2200sf Country House on 16 Acres-2 Miles to Jiminy
    Good4br Home/Apartment
    HolidayLettings
    From
    $487
  • Apartment walking distance to Mass MoCa!!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $265
  • 3 BR apartment, walking distance to Mass MoCa
     3br Home/Apartment
    HolidayLettings
    From
    $275
  • ROOM walking distance to Mass MoCa
     Home/Apartment
    HolidayLettings
    From
    $176

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
68°
6
62°
3
66° -16°
4
76°
3
52°
3
69° 17°
3
87° 37°
1
92° 41°
3
94° 45°
5
90° 50°
7
90° 41°
6
81° 24°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Cheshire. The warmest months in Cheshire are June and July, when temperatures reach 94 ˚F. The coolest month is December, when temperatures drop to -16 ˚F. The wettest month in Cheshire is May with 7.48 inches of rain, while the driest month is August with 1.49 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 travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — 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

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