Compare Cheap Hotels in Cheshire
Secret Bargains - Save an extra 10% or more on select hotels
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
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 19 - Jan 20
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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$125 nightly
The price is $140 total per night
$140 total
Feb 2 - Feb 3
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 & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$98 nightly
The price is $109 total per night
$109 total
Jan 23 - Jan 24
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$93 nightly
The price is $103 total per night
$103 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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $136 total per night
$136 total
Feb 16 - Feb 17
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
Berkshires Untold
194 Pittsfield Rd Lenox MA
$90 nightly
The price is $101 total per night
$101 total
Jan 20 - Jan 21
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
$130 nightly
The price is $145 total per night
$145 total
Jan 19 - Jan 20
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 Red Lion Inn
30 Main Street Stockbridge MA
$195 nightly
The price is $218 total per night
$218 total
Jan 19 - Jan 20
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.
Huttopia Berkshires
312 Kittle Rd Williamstown MA
$191 nightly
The price is $214 total per night
$214 total
Jan 22 - Jan 23
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.
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
Feb 6 - Feb 7
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.
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 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
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.
Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.
Cheshire hotels essential information
Accommodation | 981 hotels |
|---|---|
Lowest Price | $85 |
Highest Price | $218 |
Popular hotels | Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshire Mountain Lodge, The Williams Inn, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, Huttopia Berkshires , The Black Swan Lee - Lenox, an Ascend Collection Hotel, Best Western Plus Berkshire Hills Inn & Suites |
Most Recent Cheshire Hotel Reviews
The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"As usual at the Yankee, check-in was friendly and quick. Room was clean and had everything in order. Rate was very reasonable.,"
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
- New England Hotels
- Upstate New York Hotels
- Lenox Hotels
- The Berkshires Hotels
- Pittsfield Hotels
- Hudson Valley Hotels
- Wilmington Hotels
- Lee Hotels
- Bennington Hotels
- North Adams Hotels
- Appalachian Mountains Hotels
- Hudson River Valley Hotels
- Western Massachusetts Hotels
- Green Mountains Hotels
- Becket Hotels
- Southern Vermont Hotels
- Adams Hotels
- Lanesborough Hotels
- Mid-Atlantic Hotels
More to Explore in Cheshire
Top Picks
Hotels
- Cheap Hotels in Wareham
- Cheap Hotels in Northampton
- Cheap Hotels in New Bedford
- Cheap Hotels in Savannah
- Cheap Hotels in Pittsfield
- 5 Star Hotels in Northampton
- Cheap Hotels in Nantucket
- Cheap Hotels in Merrimac
- Cheap Hotels in Palm Springs
- Cheap Hotels in Falmouth
- Cheap Hotels in Lenox
- Cheap Hotels in Chatham
- Cheap Hotels in Manchester-by-the-Sea
- Cheap Hotels in Gloucester
- Cheap Hotels in Hyannis
- Cheap Hotels in Myrtle Beach
- Cheap Hotels in Eastham
- Cheap Hotels in Mansfield
- Cheap Hotels in Worcester
- Cheap Hotels in Fall River
- Cheap Hotels in Springfield
- Cheap Hotels in Newburyport
- Cheap Hotels in Plymouth
Flights
