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Cheap Cheshire Hotels

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$87 nightly
The price is $97 total per night
$97 total
Apr 26 - Apr 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
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$110 nightly
The price is $123 total per night
$123 total
Apr 26 - Apr 27
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
6.49 mi from city center
Located in Williamstown, Vacation Village in the Berkshires is a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
May 24 - May 25
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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$192 nightly
The price is $214 total per night
$214 total
Apr 30 - May 1
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.76 mi from city center
When you stay at The Red Lion Inn in Stockbridge, you'll be next to a golf course, within a 15-minute drive of National Shrine of the Divine Mercy and Tanglewood Music Center.
Pool
Spa
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
$130 nightly
The price is $145 total per night
$145 total
Apr 26 - Apr 27
Total with taxes and fees
Free Cancellation
20.67 mi from city center
When you 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 National Shrine of the Divine Mercy and Tanglewood Music Center.
Pool
Air conditioning
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
$329 nightly
The price is $368 total per night
$368 total
May 3 - May 4
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
$133 nightly
The price is $149 total per night
$149 total
May 14 - May 15
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
$110 nightly
The price is $123 total per night
$123 total
Apr 30 - May 1
Total with taxes and fees
Free Cancellation
17.32 mi from city center
When you stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.
Breakfast included
Pet friendly
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
$114 nightly
The price is $127 total per night
$127 total
Apr 28 - Apr 29
Total with taxes and fees
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 Kennedy Park.
Pool
Breakfast included
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night
$166 total
Apr 26 - Apr 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
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd Lenox MA
$79 nightly
The price is $88 total per night
$88 total
Apr 25 - Apr 26
Total with taxes and fees
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
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
$152 nightly
The price is $169 total per night
$169 total
Apr 28 - Apr 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.94 mi from city center
Located in Lenox, Courtyard by Marriott Lenox Berkshires is a 1-minute drive from Kennedy Park and 6 minutes from The Mount.
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.

Cheshire hotels essential information

Accommodation
1,014 hotels
Lowest Price
$88
Highest Price
$368
Popular hotels
Berkshires Untold, Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Williams Inn, Hotel Downstreet, an Ascend Collection Hotel, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hampton Inn & Suites Berkshires-Lenox, Hotel On North, Howard Johnson by Wyndham Lenox, Courtyard by Marriott Lenox Berkshires

Most Recent Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Posted 7 hours ago
CheapTickets Verified Review
"Overall it was ok. Nothing too special. Pros: Spacious and kitchen appliances fully working. Nice glasses and cutlery. Cons: Elevator Maintenance was expired and no housekeeping during stay. Massive hole in screen door."
A verified traveler stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge

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