Book Cheap Hotels in Cheshire
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Most frequently booked Cheshire hotels
Hotel Downstreet
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
15.79 km from city centre
The price is CA $167 per night
CA $167
CA $187 total
includes taxes & fees
17 Feb - 18 Feb
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 Massachusetts Museum of Contemporary Art and Studio 21 South are located nearby.
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
The price is CA $194 per night
CA $194
CA $228 total
includes taxes & fees
2 Feb - 3 Feb
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Kitchen
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
21.55 km from city centre
The price is CA $140 per night
CA $140
CA $156 total
includes taxes & fees
2 Feb - 3 Feb
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
The Williams Inn
101 Spring Street, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
16.77 km from city centre
The price is CA $273 per night
CA $273
CA $305 total
includes taxes & fees
2 Feb - 3 Feb
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts are located nearby.
Pet-friendly
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
190 Meadow Street, South Lee, MA
Free cancellation
33.29 km from city centre
The price is CA $186 per night
CA $186
CA $228 total
includes taxes & fees
2 Feb - 3 Feb
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
One West Street, Pittsfield, MA
Free cancellation
14.74 km from city centre
The price is CA $153 per night
CA $153
CA $171 total
includes taxes & fees
7 Feb - 8 Feb
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.
The Red Lion Inn
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
33.43 km from city centre
The price is CA $215 per night
CA $215
CA $304 total
includes taxes & fees
9 Feb - 10 Feb
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 Schantz Galleries and Mission House are located nearby.
Pool
Spa
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
The price is CA $148 per night
CA $148
CA $165 total
includes taxes & fees
2 Mar - 3 Mar
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 Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
27.9 km from city centre
The price is CA $141 per night
CA $141
CA $158 total
includes taxes & fees
2 Feb - 3 Feb
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
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.
Top hotels in Cheshire for Extended Stay
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10/10 Exceptional! (2 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 | 942 hotels |
---|---|
Lowest Price | CA $140 |
Highest Price | CA $273 |
Popular hotels | Hotel Downstreet, Vacation Village in the Berkshires, Life House Berkshires, The Williams Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection |
Frequently asked questions
Recent Cheshire hotel reviews by fellow wanderers
The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 12 hours ago
Travelocity Verified Review
"Surprisingly excellent property. Desk staff was superb and gracious in handling a reservation foul-up (not their fault). Would gladly return!"
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
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