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Cheshire Vacation Rentals

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Our Favorite Vacation Rentals in Cheshire

  • 2200sf Country House on 16 Acres-2 Miles to Jiminy
    2200sf Country House on 16 Acres-2 Miles to Jiminy
    Good4br Home/Apartment
    HolidayLettingsFrom $487
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  • Christmas in The Berkshires
    Christmas in The Berkshires
     1br Home/Apartment
    HolidayLettingsFrom $361
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  • Golden Triangle in the Berkshires
    Golden Triangle in the Berkshires
    Nice2br Home/Apartment
    HolidayLettingsFrom $3140
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  • Apartment walking distance to Mass MoCa!!
    Apartment walking distance to Mass MoCa!!
    Excellent2br Home/Apartment
    HolidayLettingsFrom $233
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  • Sweet Berkshire Getaway
    Sweet Berkshire Getaway
     2br Home/Apartment
    HolidayLettingsFrom $313
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  • The Bear Den
    The Bear Den
     1br Home/Apartment
    HolidayLettingsFrom $214
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  • INTERIOR DESIGNERS BOTANICAL COTTAGE
    INTERIOR DESIGNERS BOTANICAL COTTAGE
    Excellent1br Cottage
    HolidayLettingsFrom $281
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  • Jiminy Peak Ski Resort-Country Village's Best Unit
    Jiminy Peak Ski Resort-Country Village's Best Unit
    Nice2br Home/Apartment
    HolidayLettingsFrom $314
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See all 24 deals in Cheshire

Cheshire Vacation Rentals with a Pool

  • Berkshire Cottage for 4 near Jiminy Peak
    Berkshire Cottage for 4 near Jiminy Peak
    Good2br Home/Apartment
    AirbnbFrom $219
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  • 11-acre mid-century estate, newly renovated
    11-acre mid-century estate, newly renovated
    Excellent4br Home/Apartment
    AirbnbFrom $821
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  • Amazing Estate On 10 Acres--Close To Everything
    Amazing Estate On 10 Acres--Close To Everything
     8br Home/Apartment
    AirbnbFrom $1958
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  • The Oliver Wendell Holmes Guesthouse @ Holmesdale
    The Oliver Wendell Holmes Guesthouse @ Holmesdale
     1br Home/Apartment
    AirbnbFrom $359
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See all deals in Cheshire with a pool

Cheshire Vacation Rentals with Wi-Fi

  • Private Paradise in the Berkshires
    Private Paradise in the Berkshires
    Excellent1br Home/Apartment
    AirbnbFrom $164
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  • Large Secluded Berkshire Home
    Large Secluded Berkshire Home
    Good3br Home/Apartment
    AirbnbFrom $339
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  • Quiet 2 Bdrm Home Near Mass Moca, Clark Art
    Quiet 2 Bdrm Home Near Mass Moca, Clark Art
    Good2br Home/Apartment
    AirbnbFrom $141
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  • The Manor ensures a joyous experience
    The Manor ensures a joyous experience
    Excellent7br Home/Apartment
    AirbnbFrom $480
    View Deal
See all deals in Cheshire with WiFis

Cheshire Pet-Friendly Vacation Rentals

  • 3 BR apartment, walking distance to Mass MoCa
    3 BR apartment, walking distance to Mass MoCa
     3br Home/Apartment
    HolidayLettingsFrom $249
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  • ROOM walking distance to Mass MoCa
    ROOM walking distance to Mass MoCa
     1br Home/Apartment
    HolidayLettingsFrom $137
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  • 19th c. Renovated Barn in the Berkshires
    19th c. Renovated Barn in the Berkshires
    Excellent3br Home/Apartment
    AirbnbFrom $345
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  • Tentrr - Birch Berry Pines
    Tentrr - Birch Berry Pines
     1br Home/Apartment
    AirbnbFrom $130
    View Deal
See all deals 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
Most availability
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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

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
87º 37º
1.49
92º 41º
3.08
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
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.

What Expert Travelers Think

Destinations near Cheshire