Compare Cheap Hotels in Cheshire
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Cheap Cheshire Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
6.49 mi from city center
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 Coaster.
Pool
Parking included
The Williams Inn
101 Spring Street Williamstown MA
$197 nightly
The price is $220 total per night
$220 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.41 mi from city center
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$88 nightly
The price is $99 total per night
$99 total
Dec 20 - Dec 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
9.16 mi from city center
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 and Berkshire Athenaeum.
Pool
Pet friendly
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$92 nightly
The price is $103 total per night
$103 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.18 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Pool
Hot Tub
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.54 mi from city center
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 Marketplace.
Pool
Hot Tub
The Red Lion Inn
30 Main Street Stockbridge MA
$190 nightly
The price is $212 total per night
$212 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.76 mi from city center
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 River.
Pool
Spa
Berkshires Untold
194 Pittsfield Rd Lenox MA
$110 nightly
The price is $123 total per night
$123 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.38 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$145 nightly
The price is $162 total per night
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
20.67 mi from city center
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 Music Center and Housatonic River.
Pool
Air conditioning
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$125 nightly
The price is $140 total per night
$140 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Free Cancellation
9.8 mi from city center
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.
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
$105 nightly
The price is $117 total per night
$117 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.32 mi from city center
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$100 nightly
The price is $112 total per night
$112 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Free Cancellation
17.32 mi from city center
With a stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Breakfast included
Pet friendly
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$76 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
11.64 mi from city center
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
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.
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Cheshire hotels essential information
Accommodation | 984 hotels |
|---|---|
Lowest Price | $85 |
Highest Price | $220 |
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, Hampton Inn & Suites Berkshires-Lenox, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Best Western Plus Berkshire Hills Inn & Suites |
Most Recent Cheshire Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Everything was awesome"
A verified traveler stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
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