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

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$219 per night from 29 Apr to 30 Apr
NZ$219
includes taxes & fees
29 Apr - 30 Apr
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
The price is NZ$183 per night from 28 Apr to 29 Apr
NZ$183
includes taxes & fees
28 Apr - 29 Apr
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
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
The price is NZ$226 per night from 28 Apr to 29 Apr
NZ$226
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Save an average of 15% on thousands of hotels when you're signed in
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 1 May to 2 May
NZ$241
includes taxes & fees
1 May - 2 May
Stay at this 3-star 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 ...
Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is NZ$454 per night from 20 Apr to 21 Apr
NZ$454
includes taxes & fees
20 Apr - 21 Apr
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
The Williams Inn
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is NZ$327 per night from 29 Apr to 30 Apr
NZ$327
includes taxes & fees
29 Apr - 30 Apr
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
The Red Lion Inn
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
The price is NZ$175 per night from 28 Apr to 29 Apr
NZ$175
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is NZ$154 per night from 4 May to 5 May
NZ$154
includes taxes & fees
4 May - 5 May
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 20 Apr to 21 Apr
NZ$213
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Hotel On North
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
957 hotels
Lowest Price
NZ$154
Highest Price
NZ$454
Popular hotels
Life House Berkshires, The Yankee, Trademark Collection by Wyndham, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel Downstreet, Ascend Hotel Collection, The Williams Inn, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Constance, The Whitlock, & The Dewey By The Lenox Collection, Hotel On North

Most recent Cheshire hotel reviews

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