Compare Cheap Hotels in Cheshire
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Cheap Cheshire Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$128 nightly
The price is $143 total per night
$143 total
Feb 26 - Feb 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
Mar 26 - Mar 27
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
$188 nightly
The price is $210 total per night
$210 total
Feb 26 - Feb 27
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$93 nightly
The price is $103 total per night
$103 total
Mar 5 - Mar 6
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$103 nightly
The price is $115 total per night
$115 total
Mar 1 - Mar 2
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
$119 nightly
The price is $133 total per night
$133 total
Feb 26 - Feb 27
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
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$125 nightly
The price is $139 total per night
$139 total
Mar 8 - Mar 9
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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$111 nightly
The price is $124 total per night
$124 total
Mar 23 - Mar 24
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, steps from MCLA Gallery 51 and North Adams City Hall.
Pool
Hot Tub
The Red Lion Inn
30 Main Street Stockbridge MA
$209 nightly
The price is $233 total per night
$233 total
Mar 1 - Mar 2
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
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$98 nightly
The price is $109 total per night
$109 total
Mar 18 - Mar 19
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
Hotel On North
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night
$166 total
Feb 26 - Feb 27
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
Huttopia Berkshires
312 Kittle Rd Williamstown MA
$168 nightly
The price is $188 total per night
$188 total
Mar 8 - Mar 9
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
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.
Cheshire hotels essential information
Accommodation | 1,000 hotels |
|---|---|
Lowest Price | $103 |
Highest Price | $233 |
Popular hotels | Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Williams Inn, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel Downstreet, an Ascend Collection Hotel, The Red Lion Inn, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hotel On North, Huttopia Berkshires |
Most Recent Cheshire Hotel Reviews
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Very spacious and comfortable. Great for families."
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- The Red Lion Inn
- The Black Swan Lee - Lenox, an Ascend Collection Hotel
- Hotel On North
- Huttopia Berkshires
- Courtyard by Marriott Lenox Berkshires
- The Porches Inn at Mass MoCA
- Best Western Plus Berkshire Hills Inn & Suites
- The Cornell Inn, Lenox & The Berkshires
- Hampton Inn & Suites Berkshires-Lenox
- The Ponds at Foxhollow
- The Whitlock
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Element Lenox Berkshires
- Quality Inn
- Berkshire Inn
- Howard Johnson by Wyndham Lenox
- Willows Motel Williamstown
- New England Hotels
- Upstate New York Hotels
- Lenox Hotels
- The Berkshires Hotels
- Pittsfield Hotels
- Hudson Valley Hotels
- Lee Hotels
- Wilmington Hotels
- Bennington Hotels
- North Adams Hotels
- Hudson River Valley Hotels
- Appalachian Mountains Hotels
- Western Massachusetts Hotels
- Becket Hotels
- Lanesborough Hotels
- Adams Hotels
- Southern Vermont Hotels
- Green Mountains Hotels
- Mid-Atlantic Hotels
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