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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 AU$191 per night from 16 Dec to 17 Dec
AU$191
16 Dec - 17 Dec
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Opens in a new windowVacation Village in the Berkshires
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 AU$331 per night from 16 Dec to 17 Dec
AU$331
16 Dec - 17 Dec
includes taxes & fees
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Opens in a new windowThe Williams Inn
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 AU$156 per night from 17 Dec to 18 Dec
AU$156
17 Dec - 18 Dec
includes taxes & fees
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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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 AU$133 per night from 24 Dec to 25 Dec
AU$133
24 Dec - 25 Dec
includes taxes & fees
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$199 per night from 8 Jan to 9 Jan
AU$199
8 Jan - 9 Jan 2026
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
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 AU$319 per night from 14 Jan to 15 Jan
AU$319
14 Jan - 15 Jan 2026
includes taxes & fees
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic ...
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 AU$184 per night from 16 Dec to 17 Dec
AU$184
16 Dec - 17 Dec
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
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 refundableReserve now, pay when you stay
The price is AU$232 per night from 17 Dec to 18 Dec
AU$232
17 Dec - 18 Dec
includes taxes & fees
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 AU$209 per night from 8 Jan to 9 Jan
AU$209
8 Jan - 9 Jan 2026
includes taxes & fees
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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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

Want a break? Travel. Stressed out? Travel. Feeling hungry? Travel. You get the idea. If you're going to Cheshire and need somewhere to stay, let lastminute.com.au help. You won't find many hotels right in the centre, but there are 3 options within 10 kilometres of downtown Cheshire.

If you want to spend your nights as close as possible to the centre, The Spring's Inn and Topia Inn - An Organic Oasis are fabulous choices.

If you aren't phased by travelling 11 kilometres to get to central Cheshire, have a look at Hancock. This area has 3 accommodation options, including the Wyndham Bentley Brook and Jiminy Peak Mountain Resort.

Want more options? The Gateways Inn & Restaurant is located 25 kilometres away from the main central area, and the Hampton Terrace Inn is 25 kilometres away. We'd also recommend the Cranwell Spa and Golf Resort and the Birchwood Inn. The first is 25 kilometres from downtown, while the second is 25 kilometres away.

Beer or champagne? However you prefer to roll, you're sure to enjoy a trip to Pittsfield, 15 kilometres away. With the Crane Museum of Papermaking and the Skyline Country Club to check out, you're not gonna be short on things to do. Pittsfield hotels are the Wagon Wheel Inn and Lenox Inn. Alternatively, you could stay in Williamstown, 17 kilometres to the north of Cheshire, where you'll find the Williamstown Motel and Willows Motel Williamstown. Should you choose to stay in Williamstown, be sure to check out the 62 Center for Theater and Dance and Natural Bridge State Park.

Go 25 kilometres southwest and you'll be in Lenox, a regional centre with a population of 2,000. While you're checking out this neck of the woods, hang your camera 'round your neck and get your tourist on at Tanglewood Music Center, the Berkshire Scenic Railway Museum and Wood's Pond. Got another day or so to spare? See what's going on at the Cranwell Golf Club and Kennedy Park. Lenox has places to stay that should suit most tastes and budgets, including the Days Inn Lenox MA and Howard Johnson Express Inn - Lenox.

If you want to stay close to the airport, you can easily book a night at the Sheraton Hartford Hotel at Bradley Airport or the Holiday Inn Express & Suites Bradley Airport. And if you can't be bothered pulling out the map, Bradley International Airport is 80 kilometres from central Cheshire.

Cheshire hotels essential information

Accommodation
986 hotels
Lowest Price
AU$133
Highest Price
AU$331
Popular hotels
Vacation Village in the Berkshires, The Williams Inn, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshire Mountain Lodge, The Red Lion Inn, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel Downstreet, an Ascend Collection Hotel

Most recent Cheshire hotel reviews

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