Photo by Ed Gaffny

Cheshire Hotels from S$104

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Cheshire hotel prices

Tonight
Jun 14 - Jun 15
Tomorrow night
Jun 15 - Jun 16
This weekend
Jun 14 - Jun 16

Filter by

Popular filters
Popular filters
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top 10 trending Cheshire hotels

The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, 1,001 reviews
"AC in the room was to noise. Other than that it was all good."
The price is S$204
per night
26 Jun - 27 Jun
The Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, 316 reviews
"We have stayed in many hotels/Inns/Lodges in the past. My 5 year old daughter said, "this one is the best in which we have ever stayed." Looking forward to another stay in 6 days. Absolutely loved it."
The price is S$306
per night
20 Jun - 21 Jun
Berkshire Mountain Lodge
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, 260 reviews
"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. "
The price is S$180
per night
16 Jun - 17 Jun
Life House Berkshires
Hotel On North
Front of property – evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, 594 reviews
"Perfect stay. "
The price is S$285
per night
23 Jun - 24 Jun
Hotel On North
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 859 reviews
"Great amenities and very clean property. Hot tub facilities and timings were also good. Just wished they had offered bath robes. "
The price is S$236
per night
16 Jun - 17 Jun
Jiminy Peak Mountain Resort
Courtyard by Marriott Lenox Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, 510 reviews
"Room was so nice. Bed was comfortable. Overall glad we stayed here. "
The price is S$300
per night
11 Jul - 12 Jul
Courtyard by Marriott Lenox Berkshires
The Williams Inn
Front of property – evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, 304 reviews
"Positive experience. "
The price is S$369
per night
26 Jun - 27 Jun
The Williams Inn
Hampton Inn & Suites Berkshires-Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, 1,000 reviews
"very comfortable and convenient to Lenox and Edith Wharton home"
The price is S$310
per night
26 Jun - 27 Jun
Hampton Inn & Suites Berkshires-Lenox
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, 929 reviews
"I really liked everything about it "
The price is S$225
per night
16 Jun - 17 Jun
Hotel Downstreet
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very good, 952 reviews
"Excellent service "
The price is S$191
per night
23 Jun - 24 Jun
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, 588 reviews
"The hotel has been updated with comfortable rooms that are clean and nice. The pool area is clean. Breakfast was great. Easy, fast, and delicious. The staff went above and beyond to be helpful. The only downsides are: rooms surrounding the pool area are loud during open pool hours. Rooms could use a with noice cancelling material in the hallway walls. The parking garage is closed, but not yet under construction. So the surrounding area looks dated and rundown, but the hotel building itself...
The price is S$213
per night
16 Jun - 17 Jun
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Fairfield Inn & Suites by Marriott Williamstown
Exterior
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, 271 reviews
"Cleanliness. Conenience. Lobby decor. Friendly service. Late model hi def TV. Comfy bed."
The price is S$257
per night
19 Jun - 20 Jun
Fairfield Inn & Suites by Marriott Williamstown
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, 105 reviews
"nice comfortable and funky!"
The price is S$330
per night
16 Jun - 17 Jun
The Trail in Adams - Berkshires’ Art Hotel
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, 666 reviews
"A decent place with a close location to downtown."
The price is S$151
per night
17 Jun - 18 Jun
Berkshire Inn
Berkshire Valley Inn
Exterior
Berkshire Valley Inn
2.5 star property
9.0 out of 10, Wonderful, 506 reviews
"What a wonderful stay we had ! This place is so sweet and charming and pet friendly. The dog park is so nice and my pups loved it ! The room I had was impeccable and I slept like a baby . Can’t wait to come back ! What a cool place to visit "
The price is S$243
per night
16 Jun - 17 Jun
Berkshire Valley Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
2.5 star property
5.2 out of 10, 559 reviews
"Run down "
The price is S$104
per night
16 Jun - 17 Jun
FairBridge Inn Express
Wagon Wheel Inn
Property grounds
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, 547 reviews
"Good basic clean room. Have stayed here several times while in town for business. Great room and location for a very reasonable price"
The price is S$104
per night
16 Jun - 17 Jun
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, 615 reviews
"Clean, comfortable. Fast check-in with friendly person. Will use again"
The price is S$134
per night
16 Jun - 17 Jun
Howard Johnson by Wyndham Lenox
Stay Berkshires
Lake view
Stay Berkshires
2.0 star property
8.4 out of 10, Very good, 337 reviews
"The staff went to great lengths to solve a problem that arose with my reservation. I would strongly recommend Stay Berkshire for a visit to the Williamstown area. "
The price is S$242
per night
16 Jun - 17 Jun
Stay Berkshires
Willows Motel Williamstown
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, 801 reviews
"Clean room and comfortable bed. Quiet. Excellent breakfast options of fresh fruit, muffins, granola and bagels. Staff was friendly and courteous. "
The price is S$133
per night
16 Jun - 17 Jun
Willows Motel Williamstown
Don't see what you're looking for?
See all available properties in Cheshire
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.

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is S$134 per night from Jun 16 to Jun 17
S$134
per night
16 Jun - 17 Jun
7.6/10 Good! (614 reviews)

Hotels near Cheshire Attractions

Image for St Mary's of the Assumption Church

St Mary's of the Assumption Church

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views or seek out its ski slopes.

See properties
St Mary's of the Assumption Church

Cheshire hotels information

Number of reviews
4,414
Accommodation
877 hotels
Lowest Price
S$104
Highest Price
S$369

Frequently asked questions

If I need to cancel my hotel reservation in Cheshire, will I receive a refund?

Yes! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.

What is staying in Cheshire like?

Visitors can enjoy all that Cheshire has to offer, including the ski areas, restaurants and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 3 hotels and other accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

A couple of favourite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.

What's the seasonal weather in Cheshire?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, April, March and February, with each month seeing an average of 20 cm of snowfall.

Book Cheshire hotels on Expedia USA

Recent Reviews in Cheshire
Expedia verified reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent
"We love the proximity to Lee. Had a great dinner at the Salmon Run. Highly recommended!"
A verified traveller from Hyde Park stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel