Cheshire Vacation Rentals

Our Favorite Vacation Rentals in Cheshire

  • Tentrr - Birch Berry Pines
     Country House
    Booking.com
    From
    $115
  • Charming Berkshires lakefront house, great views
     2br Home/Apartment
    HolidayLettings
    From
    $348
  • Berkshire Cottage
     Country House
    Booking.com
    From
    $550
  • Stone School Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $230
  • Jiminy Peak Vacation Home
     Country House
    Booking.com
    From
    $300
  • NEW! Family Home w/Game Room - 3 Mi to Jiminy Peak
     4br Home/Apartment
    HolidayLettings
    From
    $502
  • Heart Of The Berkshires
    ExcellentHome/Apartment
    Booking.com
    From
    $155
  • Beautiful Berkshires Lake House w/ Private Dock!
     3br Cottage
    HolidayLettings
    From
    $623

Check prices for these upcoming dates

Cheshire Vacation Rentals with a Pool

  • Wyndham Bentley Brook * 2BR Deluxe
    Excellent2br Home/Apartment
    Airbnb
    From
    $212
  • Charming Apartment In The Heart of The Berkshires
    ExcellentHome/Apartment
    Airbnb
    From
    $170
  • 11-acre mid-century estate, newly renovated
    Excellent4br Home/Apartment
    Airbnb
    From
    $787
  • Amazing, Spacious Estate on 10 Acres
    Excellent8br Estate
    Airbnb
    From
    $1,342

Cheshire Vacation Rentals with Wi-Fi

  • 19th c. Renovated Barn in the Berkshires
    Excellent3br Home/Apartment
    Airbnb
    From
    $345
  • Private Paradise in the Berkshires
    ExcellentHome/Apartment
    Airbnb
    From
    $164
  • Large Secluded Berkshire Home
    Good3br Home/Apartment
    Airbnb
    From
    $339
  • Elmwood Farmhouse
    Excellent4br Home/Apartment
    Airbnb
    From
    $290

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
    $329
  • The Bear Den
     Home/Apartment
    HolidayLettings
    From
    $163
  • 3 BR apartment, walking distance to Mass MoCa
     3br 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
90 º41
6
81 º24
3
68 º1
6
62 º9
3
66 º-16
4
76 º0
3
52 º3
3
69 º17
3
87 º37
1
92 º41
3
94 º45
5
90 º50
7
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
  • — 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 All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

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