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Cheap Cheshire hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is NZ$219 per night from 20 Jan to 21 Jan
NZ$219
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is NZ$241 per night from 22 Jan to 23 Jan
NZ$241
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$382 per night from 24 Dec to 25 Dec
NZ$382
24 Dec - 25 Dec
includes taxes & fees
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Williams Inn
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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$147 per night from 4 Jan to 5 Jan
NZ$147
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is NZ$180 per night from 25 Dec to 26 Dec
NZ$180
25 Dec - 26 Dec
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is NZ$229 per night from 21 Jan to 22 Jan
NZ$229
21 Jan - 22 Jan 2026
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowBerkshire Mountain Lodge
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$366 per night from 14 Jan to 15 Jan
NZ$366
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Red Lion Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 24 Dec to 25 Dec
NZ$213
24 Dec - 25 Dec
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowBerkshires Untold
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
Fully refundable
The price is NZ$282 per night from 4 Jan to 5 Jan
NZ$282
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff in their ...
Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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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
982 hotels
Lowest Price
NZ$147
Highest Price
NZ$382
Popular hotels
Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, The Williams Inn, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshire Mountain Lodge, The Red Lion Inn, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Most recent Cheshire hotel reviews

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