A lake surrounded by autumn-colored trees and hills.

Search and Rent Cheshire Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Cheshire condo rentals

A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

1. UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (18 reviews)
"lovely place to stay"
United States
Nancy P.
$497 nightly
The price is $555
Nov 6 - Nov 7
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"It's a good place with beautiful views during the 🍁🍂 for a family or romantic get away"
fritzgerald 2-night trip
Posted 12 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire Condo Rentals information

Number of reviews
18
Accommodation
27 Condo Rentals
Lowest Price
$555
Highest Price
$555

Frequently asked questions

How much do condos in Cheshire cost?
Condos in Cheshire range from $555 to $555 per night. This will give you loads of room for your whole crew at a price that fits your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Cheshire?
There are 27 condos in Cheshire. Whether you're taking a trip with the little ones or organizing a weekend break with some friends, Expedia will help you find the perfect space for your squad.
Are there any family-friendly condos in Cheshire?
If you're planning an escape in Cheshire and after a family-friendly condo, we recommend Vacation Village In The Berkshires. This 3-star stay offers a garden and a swimming pool. After checking in and chilling out in your comfortable new digs, it's time to visit some of the local sights. Jiminy Peak Mountain Resort and Mount Greylock are just two family-friendly attractions in Cheshire.
Why book your condo in Cheshire with Expedia?
We think that vacations should be stress-free, so if you're seeking condos at a competitive rate, Expedia can help. Keep the budget under control and choose something small and affordable, or book a 5-star condo and spoil the ones you love most. Use our convenient search filters to find a stay in Cheshire that matches your needs.
How can I find cheap condos in Cheshire?
Expedia can help you easily source cheap condos in Cheshire. To discover your perfect stay in just a few keystrokes, simply use our convenient filter tool to refine your search results by star rating, budget and amenities.
What is there to do in Cheshire near my condo?
The most useful travel accessory is a well-planned to-do list. St Mary's of the Assumption Church is a wonderful place to kick off your adventures in Cheshire.

Explore a world of travel with Expedia