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

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is $144 per night
$144
includes taxes & fees
$129 per night
Nov 25 - Nov 26
Free Cancellation
Reserve now, pay when you stay
9.81 mi from city center
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum of Contemporary Art.
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $134 per night
$134
includes taxes & fees
$120 per night
Nov 26 - Nov 27
Free Cancellation
Reserve now, pay when you stay
13.38 mi from city center
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $104 per night
$104
includes taxes & fees
$94 per night
Dec 2 - Dec 3
Free Cancellation
Reserve now, pay when you stay
12.18 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and Company.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $184 per night
$184
includes taxes & fees
$164 per night
Dec 18 - Dec 19
Free Cancellation
Reserve now, pay when you stay
20.76 mi from city center
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
The price is $106 per night
$106
includes taxes & fees
$95 per night
Dec 15 - Dec 16
Free Cancellation
Reserve now, pay when you stay
17.32 mi from city center
When you stay at The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, you'll be on the waterfront, within a 5-minute drive of Berkshire Mountain Country Store and Animagic Museum of Animation.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $195 per night
$195
includes taxes & fees
$178 per night
Nov 25 - Nov 26
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.
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
The price is $106 per night
$106
includes taxes & fees
$95 per night
Nov 30 - Dec 1
Free Cancellation
9.15 mi from city center
A stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel places you in the heart of Pittsfield, within a 5-minute walk of Berkshire Museum and Colonial Theater.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $127 per night
$127
includes taxes & fees
$114 per night
Nov 26 - Nov 27
Free Cancellation
20.67 mi from city center
Located in South Lee, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel is near ski lifts, within a 5-minute walk of Beartown State Forest and Housatonic River.
Pool
Restaurant
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $100 per night
$100
includes taxes & fees
$89 per night
Nov 25 - Nov 26
15.54 mi from city center
With a stay at The Constance, The Whitlock, & The Dewey By The Lenox Collection in Lenox, you'll be within a 5-minute walk of Lenox Library and The Bookstore.
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is $216 per night
$216
includes taxes & fees
$193 per night
Dec 5 - Dec 6
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.
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
The price is $132 per night
$132
includes taxes & fees
$118 per night
Dec 14 - Dec 15
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 Arrowhead Museum.
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
The price is $88 per night
$88
includes taxes & fees
$79 per night
Dec 8 - Dec 9
Free Cancellation
Reserve now, pay when you stay
18.52 mi from city center
With a stay at Quality Inn in Lee, you'll be a 1-minute walk from Housatonic River and 12 minutes by foot from Lee Library.
Don't see what you're looking for?
See all available properties in Cheshire
View all properties
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
903 hotels
Lowest Price
$88
Highest Price
$216
Popular hotels
Hotel Downstreet, Life House Berkshires, The Yankee, Trademark Collection by Wyndham, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Constance, The Whitlock, & The Dewey By The Lenox Collection, The Williams Inn, Hampton Inn & Suites Berkshires-Lenox, Quality Inn

Most Recent Cheshire Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Pretty view of the Lake"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection