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Cheap Cheshire Hotels

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is $142 per night
$142
includes taxes & fees
$127 per night
Jul 28 - Jul 29
Free Cancellation
Reserve now, pay when you stay
9.81 mi from city center
With a stay at Hotel Downstreet, you'll be centrally located in North Adams, within a 10-minute drive of Williams College and Western Gateway Heritage State Park.
Pool
Hot Tub
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $182 per night
$182
includes taxes & fees
$163 per night
Aug 12 - Aug 13
Free Cancellation
Reserve now, pay when you stay
13.38 mi from city center
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $246 per night
$246
includes taxes & fees
$220 per night
Jul 30 - Jul 31
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $160 per night
$160
includes taxes & fees
$144 per night
Aug 7 - Aug 8
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.
Pool
Hot Tub
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 $210 per night
$210
includes taxes & fees
$188 per night
Jul 29 - Jul 30
17.32 mi from city center
With a stay at The Black Swan Lee - Lenox, Ascend Hotel Collection 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
The Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $131 per night
$131
includes taxes & fees
$117 per night
Jul 29 - Jul 30
15.54 mi from city center
With a stay at The Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox Library.
Breakfast included
Parking included
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 $189 per night
$189
includes taxes & fees
$169 per night
Jul 29 - Jul 30
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
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
Jul 28 - Jul 29
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 $147 per night
$147
includes taxes & fees
$131 per night
Aug 25 - Aug 26
Free Cancellation
9.15 mi from city center
With a stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Colonial Theater.
Pool
Pet friendly
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is $302 per night
$302
includes taxes & fees
$270 per night
Jul 29 - Jul 30
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is $227 per night
$227
includes taxes & fees
$205 per night
Jul 28 - Jul 29
Free Cancellation
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
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is $122 per night
$122
includes taxes & fees
$109 per night
Jul 29 - Jul 30
Free Cancellation
Reserve now, pay when you stay
12.19 mi from city center
With a stay at Howard Johnson by Wyndham Lenox in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Parking included
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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
898 hotels
Lowest Price
$122
Highest Price
$302
Popular hotels
Hotel Downstreet, Life House Berkshires, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Lenox Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, The Williams Inn, Berkshire Mountain Lodge, Howard Johnson by Wyndham Lenox

Most Recent Cheshire Hotel Reviews

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

5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Pleasant stay with the family"
A verified traveler from Fair lawn stayed at 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

Top 20 Cheshire Hotels

Hotels Near Cheshire

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