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Cheshire Vacation Rentals
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Vacation Rentals in Cheshire
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, 859 reviews
The price is ¥24,974
per night
Jun 17 - Jun 18
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 8 reviews
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, 186 reviews
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Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, 117 reviews
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, 28 reviews
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, 6 reviews
Bear Creek Cabin
Bear Creek Cabin
10.0 out of 10, Exceptional, 14 reviews
The price is ¥62,828
per night
Jun 17 - Jun 18
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, 205 reviews
Berkshire Lake access
Berkshire Lake access
10.0 out of 10, Exceptional, 41 reviews
Fox Hollow Luxury Ranch Laurel Lake
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, 12 reviews
Private Lake House in the Berkshires
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 15 reviews
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
Quintessential 6-BR Berkshires Lodge
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, 4 reviews
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, 36 reviews
Tranquil 3-BR Waterfront Retreat
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
Rockspring by AvantStay | Huge Berkshires Estate
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, 10 reviews
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, 12 reviews
The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, 15 reviews
Amore Estate - sleeps 12 in beds
Amore Estate - sleeps 12 in beds
9.6 out of 10, Exceptional, 8 reviews
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other types of properties in Cheshire you may be interested in
Hotel Downstreet
Hotel Downstreet
8.6 out of 10, Excellent, 929 reviews
The price is ¥23,403
per night
Jun 17 - Jun 18
Life House Berkshires
Life House Berkshires
9.0 out of 10, Wonderful, 260 reviews
The price is ¥18,691
per night
Jun 17 - Jun 18
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.0 out of 10, Wonderful, 1,001 reviews
The price is ¥22,477
per night
Jun 16 - Jun 17
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions
Recent reviews of Cheshire propertiesExpedia verified reviews
![Life House Berkshires](http://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257_y.jpg)
Life House Berkshires
5/5 Excellent
Modern, friendly and clean
"From my kind greeting from Bobby to my checkout in the morning, my stay could not have been better. Clean and up to date rooms, a great bar and friendly staff. Will definitely come back. "
A verified traveler stayed at Life House Berkshires
Posted 1 day ago