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Cheshire Vacation Rentals

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Our Favorite Vacation Rentals in Cheshire

  • Heart Of The Berkshires
    Heart Of The Berkshires
     
    Booking.comFrom $155
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  • Charming Berkshires lakefront house, great views
    Charming Berkshires lakefront house, great views
     
    HolidayLettingsFrom $329
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  • Stone School Cottage
    Stone School Cottage
    Excellent
    HolidayLettingsFrom $229
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  • Nestled in the Berkshire Hills, The Manor ensures a joyous experience!
    Nestled in the Berkshire Hills, The Manor ensures a joyous experience!
     
    HolidayLettingsFrom $458
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  • Stunning Private Suite in the Beautiful Berkshires
    Stunning Private Suite in the Beautiful Berkshires
     
    HolidayLettingsFrom $186
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  • Whitman Woods - A Berkshire Vacation
    Whitman Woods - A Berkshire Vacation
    Excellent
    HolidayLettingsFrom $300
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  • 2200sf Country House on 16 Acres-2 Miles to Jiminy
    2200sf Country House on 16 Acres-2 Miles to Jiminy
    Good
    HolidayLettingsFrom $444
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  • Christmas in The Berkshires
    Christmas in The Berkshires
     
    HolidayLettingsFrom $345
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See all 26 vacation rentals in Cheshire

Cheshire Vacation Rentals with a Pool

  • Wyndham Bentley Brook * 2BR Deluxe
    Wyndham Bentley Brook * 2BR Deluxe
    Excellent
    AirbnbFrom $294
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  • Getaway cabin for lovers
    Getaway cabin for lovers
     
    AirbnbFrom $1037
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  • Lovely Home with a Private Yard
    Lovely Home with a Private Yard
     
    AirbnbFrom $675
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  • Berkshires - Hancock, Bentley Brook
    Berkshires - Hancock, Bentley Brook
    Excellent
    AirbnbFrom $279
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See all vacation rentals in Cheshire with a pool

Cheshire Vacation Rentals with Wi-Fi

  • 19th c. Renovated Barn in the Berkshires
    19th c. Renovated Barn in the Berkshires
    Excellent
    AirbnbFrom $336
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  • Large Secluded Berkshire Home
    Large Secluded Berkshire Home
    Good
    AirbnbFrom $344
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  • Berkshire Gorge House/Williamstown
    Berkshire Gorge House/Williamstown
    Good
    AirbnbFrom $322
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  • Berkshire farmhouse on gorgeous working farm.
    Berkshire farmhouse on gorgeous working farm.
    Excellent
    AirbnbFrom $440
    View Deal
See all vacation rentals in Cheshire with WiFis

Cheshire Pet-Friendly Vacation Rentals

  • Apartment walking distance to Mass MoCa!!
    Apartment walking distance to Mass MoCa!!
    Excellent
    HolidayLettingsFrom $619
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  • House On Main Street
    House On Main Street
     
    HolidayLettingsFrom $1312
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  • The Bear Den
    The Bear Den
     
    HolidayLettingsFrom $151
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  • ROOM walking distance to Mass MoCa
    ROOM walking distance to Mass MoCa
     
    HolidayLettingsFrom $601
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See all vacation rentals in Cheshire that allow pets

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
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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 1º
5.5
62º 9º
3.12
66º -16º
3.92
76º 0º
2.59
52º 3º
3.15
69º 17º
3.28
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
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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