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 $186 total
includes taxes & fees
5 Jan - 6 Jan 2025
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.
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 $139 per night
CA $139
CA $155 total
includes taxes & fees
29 Dec - 30 Dec
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.
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 $127 per night
CA $127
CA $142 total
includes taxes & fees
1 Jan - 2 Jan 2025
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 Kennedy Park and Pleasant Valley Wilderness Sanctuary 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 $185 per night
CA $185
CA $271 total
includes taxes & fees
1 Jan - 2 Jan 2025
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 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 $145 per night
CA $145
CA $162 total
includes taxes & fees
30 Dec - 31 Dec
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 Berkshire Mountain Country Store and Animagic Museum of Animation are located nearby.
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 $142 per night
CA $142
CA $159 total
includes taxes & fees
5 Jan - 6 Jan 2025
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.
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 $185 per night
CA $185
CA $227 total
includes taxes & fees
6 Jan - 7 Jan 2025
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 Berkshire Theatre Festival and Schantz Galleries are located nearby.
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 $267 per night
CA $267
CA $299 total
includes taxes & fees
2 Jan - 3 Jan 2025
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.
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 $269 per night
CA $269
CA $310 total
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, 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.
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! (1 review)
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 | 923 hotels |
---|---|
Lowest Price | CA $127 |
Highest Price | CA $269 |
Popular hotels | Hotel Downstreet, The Yankee, Trademark Collection by Wyndham, Life House Berkshires, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Williams Inn, Vacation Village in the Berkshires |
Frequently asked questions
Recent Cheshire hotel reviews by fellow wanderers
The Constance, The Whitlock, & The Dewey By The Lenox Collection
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"It was amazing! The staff was incredible, the room was very clean and cozy, and overall was a great place to stay. Loved it here!"
A verified traveller stayed at The Constance, The Whitlock, & The Dewey By The Lenox Collection
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