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 26 - Jan 27
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $136 total per night
$136 total
Feb 22 - Feb 23
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 Williams Inn
101 Spring Street Williamstown MA
$186 nightly
The price is $208 total per night
$208 total
Jan 25 - Jan 26
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.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$98 nightly
The price is $109 total per night
$109 total
Jan 30 - Jan 31
Total with taxes and fees
Free Cancellation
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
Berkshires Untold
194 Pittsfield Rd Lenox MA
$90 nightly
The price is $101 total per night
$101 total
Jan 29 - Jan 30
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.
Pet friendly
Parking included
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$126 nightly
The price is $140 total per night
$140 total
Feb 10 - Feb 11
Total with taxes and fees
Free Cancellation
9.78 mi from city center
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, within a 5-minute walk of MCLA Gallery 51 and North Adams City Hall.
Pool
Hot Tub
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$130 nightly
The price is $145 total per night
$145 total
Jan 25 - Jan 26
Total with taxes and fees
Free Cancellation
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$98 nightly
The price is $110 total per night
$110 total
Jan 25 - Jan 26
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
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$94 nightly
The price is $105 total per night
$105 total
Jan 25 - Jan 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.
Breakfast included
Pet friendly
The Red Lion Inn
30 Main Street Stockbridge MA
$189 nightly
The price is $211 total per night
$211 total
Jan 25 - Jan 26
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
Huttopia Berkshires
312 Kittle Rd Williamstown MA
$225 nightly
The price is $251 total per night
$251 total
Feb 1 - Feb 2
Total with taxes and fees
8.34 mi from city center
With a stay at Huttopia Berkshires in Williamstown, you'll be within a 10-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Pool
Pet friendly
Hotel On North
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night
$166 total
Jan 25 - Jan 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
8.83 mi from city center
Located in Pittsfield, Hotel On North is a 1-minute drive from Barrington Stage Company and 7 minutes from Bousquet Ski Area.
Pet friendly
Parking included
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 | 991 hotels |
|---|---|
Lowest Price | $101 |
Highest Price | $251 |
Popular hotels | Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Williams Inn, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, Hotel Downstreet, an Ascend Collection Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Best Western Plus Berkshire Hills Inn & Suites, The Red Lion Inn, Huttopia Berkshires , Hotel On North |
Most Recent Cheshire Hotel Reviews
Berkshire Mountain Lodge
5 out of 5
Posted 19 hours ago
CheapTickets Verified Review
"Great kitchen! Helpful staff, very convenient location. "
A verified traveler stayed at Berkshire Mountain Lodge
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