A lake surrounded by autumn-colored trees and hills.

Cheshire Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Cheshire vacation rentals

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1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,517 reviews)
"I have been visiting this property for years and it is always great. Can’t beat it after a few days of adventure in the Berkshires"
United States
Brooks
The price is P5,893
P7,251 total
includes taxes & fees
Sep 2 - Sep 3
Vacation Village in the Berkshires
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2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,059 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is P5,766
P7,802 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
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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Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Pensamos volver pronto"
Jose 3-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Find out more about Cheshire

Search for holiday rentals in Cheshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire using one of the methods below:

  • View our selection of featured holiday rentals in Cheshire
  • Use the map to find apartments and other holiday homes in the Cheshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheshire while they last

Look no further and take a look at our great range of rental properties in Cheshire!

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we offer vacation rentals close to the most popular sights in Cheshire, or you can go with a more remote option if you're looking for relaxation. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

How many vacation rentals are there in Cheshire?

Expedia has 5 vacation rentals for your stay in Cheshire.

What can I see and do in Cheshire?

Mount Greylock State Reservation and Cheshire Reservoir are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are vacation rentals like in Cheshire?

Vacation rentals are private properties you can reserve for a couple days or more in Cheshire. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.