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Cheshire Vacation Rentals

Our Favorite Vacation Rentals in Cheshire

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Cheshire Vacation Rentals with a Pool

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Cheshire Vacation Rentals with Wi-Fi

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Cheshire Pet-Friendly Vacation Rentals

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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

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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 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 Weather in Cheshire

87º 37º
1.49
92º 41º
3.08
94º 45º
5.26
90º 50º
7.48
90º 41º
6.18
81º 24º
2.77
68º
5.5
62º
3.12
66º -16º
3.92
76º
2.59
52º
3.15
69º 17º
3.28
May
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Sep
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Rainy days
This climate histogram shows you the weather patterns in Cheshire. The hottest month in Cheshire is June, when temperatures peak at 94 ˚F. The coolest month is January, when temperatures drop to -16 ˚F. The wettest month in Cheshire is August with 7.48 inches of rain, while the driest month is May with 1.49 inches of rain.

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