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Check prices for these dates

Next weekend
Mar 28 - Mar 30
In two weeks
Apr 4 - Apr 6
In one month
Apr 18 - Apr 20
In two months
May 16 - May 18

Browse Select Cheshire Villas

The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
7 nights in our 1 br, full kitchen villa. Only 110 per night
Indoor pool, outdoor pool

7 nights in our 1 br, full kitchen villa. Only 110 per night

7 nights in our 1 br, full kitchen villa. Only 110 per night
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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Other property types in Cheshire

19th c. Barn in the Berkshires
Interior

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"Amazing property, very clean- "
19th c. Barn in the Berkshires
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is CA $167
CA $198 total
includes taxes & fees
Mar 25 - Mar 26
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is CA $213
CA $234 total
includes taxes & fees
Apr 11 - Apr 12
Jiminy Peak Mountain Resort
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.

Frequently asked questions

Why book your villa in Cheshire with Expedia?
Booking a villa in Cheshire is as easy as entering your travel dates and selecting an option that has what you need. Looking for something budget friendly or upmarket, or a stay that also includes a kitchenette? Use Expedia’s search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Cheshire?
With Expedia’s filter tool, reserving cheap villas in Cheshire has never been easier. To discover accommodations that are easy on the wallet, narrow your search results by budget, amenities and star rating.
What is there to do near my villa in Cheshire?
If you’d like to see the sights of Cheshire, check out St Mary’s of the Assumption Church. It’s popular with locals and tourists alike.