Book Cheap Hotels in Cheshire
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Most frequently booked Cheshire hotels

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
10.45 km from city centre
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
19.61 km from city centre
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free cancellation
Reserve now, pay when you stay
33.29 km from city centre
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free cancellation
Reserve now, pay when you stay
18.74 km from city centre
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Tracy Brook Wildlife Sanctuary are located nearby.
Breakfast included
Pet-friendly

Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
15.79 km from city centre
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
21.55 km from city centre
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free cancellation
14.75 km from city centre
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly

The Constance by the Lenox Collection
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
25.02 km from city centre
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
Breakfast included
Pet-friendly

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
33.43 km from city centre
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Pool
Spa
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.
Top hotels in Cheshire for Extended Stay

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10/10 Exceptional! (4 reviews)
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 | 985 hotels |
---|---|
Lowest Price | |
Highest Price | |
Popular hotels | Vacation Village in the Berkshires, The Yankee, Trademark Collection by Wyndham, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites, Hotel Downstreet, Ascend Hotel Collection, Berkshires Untold, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Constance by the Lenox Collection, The Red Lion Inn |
Frequently asked questions
Recent Cheshire hotel reviews by fellow wanderers

Holiday Inn & Suites Pittsfield-Berkshires by IHG
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"All was great, except parking was quiet of walk "
A verified traveller stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG
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