AllTheRooms.

Cheshire Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. Massachusetts
  4. Cheshire

Check prices for these upcoming dates

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.

More+

Price and Availability in Cheshire

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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.
More+

The Weather in Cheshire

Rainy days
65° 18°
4
41° -10°
3
50° -3°
3
76° 8°
2
77° 17°
4
89° 33°
4
93° 43°
4
87° 47°
12
92° 49°
5
85° 42°
8
78° 31°
6
69° 16°
2
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Rainy days

This climate histogram shows you the weather patterns in Cheshire. The warmest months in Cheshire are July and May, when temperatures reach 93 ˚F. The coolest month is December, when temperatures drop to -10 ˚F. The wettest month in Cheshire is June with 12.15 inches of rain, while the driest month is October with 2.08 inches of rain.

More+

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
    Visit Amanda Alston

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
    Visit Coco Travels

  • — 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
    Visit ILIKETODABBLE

Destinations near Cheshire

  • Boston3,441 Properties
  • Nantucket3,241 Properties
  • Provincetown2,272 Properties
  • Eastham1,663 Properties
  • Dennis Port1,632 Properties
  • Chatham1,575 Properties
  • Brewster1,460 Properties
  • Wellfleet1,323 Properties
  • Orleans1,230 Properties
  • Oak Bluffs1,137 Properties
  • Somerville1,045 Properties
  • Edgartown1,004 Properties
  • West Yarmouth913 Properties
  • Cambridge870 Properties
  • Falmouth869 Properties
  • Mashpee859 Properties
  • Hyannis808 Properties
  • South Yarmouth791 Properties
  • Brookline765 Properties
  • Tisbury714 Properties
  • Plymouth678 Properties
  • Rockport673 Properties
  • East Falmouth670 Properties
  • West Dennis627 Properties
  • North Truro612 Properties
  • Gloucester608 Properties
  • South Chatham599 Properties
  • Lenox539 Properties
  • Harwich533 Properties
  • Worcester492 Properties
  • Salem474 Properties
  • Dennis472 Properties
  • Harwich Port463 Properties
  • East Sandwich442 Properties
  • Centerville441 Properties
  • Hancock430 Properties
  • Revere415 Properties
  • Great Barrington411 Properties
  • Vineyard Haven401 Properties
  • Waltham389 Properties
  • Lee368 Properties
  • Quincy357 Properties
  • Northampton357 Properties
  • Sandwich352 Properties
  • Newton341 Properties
  • Truro339 Properties
  • Medford326 Properties
  • Watertown323 Properties
  • Williamstown315 Properties
  • Newburyport312 Properties
  • Marblehead304 Properties
  • Pittsfield300 Properties
  • South Dennis290 Properties
  • North Falmouth267 Properties
  • Chelsea266 Properties
  • Amherst257 Properties
  • Stockbridge246 Properties
  • Marshfield242 Properties
  • Osterville232 Properties
  • Barnstable232 Properties
  • Arlington231 Properties
  • Wareham207 Properties
  • Scituate200 Properties
  • West Harwich198 Properties
  • Woburn186 Properties
  • Chilmark172 Properties
  • Bourne164 Properties
  • Sturbridge155 Properties
  • Fairhaven138 Properties
  • Winthrop130 Properties
  • Ipswich120 Properties
  • Westport117 Properties
  • West Stockbridge109 Properties
  • Marlborough108 Properties
  • Hull97 Properties
  • New Marlborough89 Properties
  • Sheffield81 Properties
  • Manchester76 Properties
  • Springfield65 Properties
  • Concord65 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Hubbardston8 Properties