Book Cheshire hotels

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Check hotel availability in Cheshire

Cheap Cheshire hotels

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 23 Jun to 24 Jun
NZ$272
per night
23 Jun - 24 Jun
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Downstreet
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 24 Jun to 25 Jun
NZ$217
per night
24 Jun - 25 Jun
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Life House Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 26 Jun to 27 Jun
NZ$228
per night
26 Jun - 27 Jun
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
Save an average of 15% on thousands of hotels when you're signed in
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$245 per night from 24 Jun to 25 Jun
NZ$245
per night
24 Jun - 25 Jun
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$362 per night from 26 Jun to 27 Jun
NZ$362
per night
26 Jun - 27 Jun
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our ...
The Red Lion Inn
The Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is NZ$191 per night from 23 Jun to 24 Jun
NZ$191
per night
23 Jun - 24 Jun
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Lenox Collection
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

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is NZ$272 per night from 24 Jun to 25 Jun
NZ$272
per night
24 Jun - 25 Jun
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the clean ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$162 per night from 24 Jun to 25 Jun
NZ$162
per night
24 Jun - 25 Jun
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Lenox
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$231 per night from 7 Jul to 8 Jul
NZ$231
per night
7 Jul - 8 Jul
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Quality Inn
Don't see what you're looking for?
See all available properties in Cheshire
View all properties
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.

Hotels In Cheshire

For those visitors searching for accommodation options close to Cheshire's heart, there are a number of options within a 10-kilometre radius.

There is a range of accommodations within driving distance, including the The Spring's Inn and The Weathervane Motel.

The Rookwood Inn is located 25 kilometres from the middle of Cheshire. Or, alternatively, the Gateways Inn & Restaurant is 25 kilometres away. The Hampton Terrace Inn and also the Cranwell Spa and Golf Resort are some alternative places to stay in Cheshire.

Once you have really explored Cheshire, why don't you tour a little further afield? The Western Massachusetts region has plenty of other scenic and cultural delights waiting to be explored. Admire Western Massachusetts's mountains. If that's not your idea of a good time, spend time at the region's history museums. Adventurous visitors may also enjoy skiing, cross-country skiing and mountain biking in this part of United States of America.

Looking for more things to do? Kick back and spend the day exploring the Lee Prime Outlets and Tyringham Cobble, which you'll find in Lee, 30 kilometres to the south of Cheshire. The Black Swan Inn, an Ascend Collection Hotel and Chambery Inn are some of the great apartment and hotel options in Lee. Alternatively, you could stay in Lenox, 25 kilometres to the southwest of Cheshire, where you can pick from the Birchwood Inn and Hampton Inn & Suites Berkshires Lenox. The Shakespeare and Company and Tanglewood Music Center are amongst the more popular attractions to experience while in Lenox.

Sport lover? Indulge in your passion by visiting Times Union Center, 50 kilometres to the west of Cheshire. Planning to stay near the action? The Hilton Albany and the TownePlace Suites by Marriott Albany Downtown/Medical Center could both be ideal.

Albany International Airport is the most used airport for flying into Cheshire and is 55 kilometres from the heart of town. If you plan to stay nearby, try the Residence Inn by Marriott Albany Airport or the The Desmond Hotel and Conference Center.

Cheshire hotels essential information

Accommodation
873 hotels
Lowest Price
NZ$162
Highest Price
NZ$362
Popular hotels
Hotel Downstreet, Life House Berkshires, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Red Lion Inn, The Lenox Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, Howard Johnson by Wyndham Lenox, Quality Inn

Most recent Cheshire hotel reviews

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.