Find hotels in Cheshire, MA from ₩82,279
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Cheshire
Family friendly
Check prices for these dates
Our top choices for Cheshire hotels
9.4 out of 10, Exceptional, (53)
Unwind at this cozy Cheshire inn offering free WiFi and parking. Explore nearby Mount Greylock State Reservation or catch a show at Adams Theater, then return to comfortable accommodations just 16 minutes from Pittsfield Station.
"Nice place for a weekend away."
Gregory
The price is ₩310,587
₩328,291 total
includes taxes & fees
Jan 7 - Jan 8
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1002)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness center or enjoy nearby skiing options. Tanglewood Music Center and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.
"Very friendly and good Breakfast."
Jesse
The price is ₩110,330
₩123,239 total
includes taxes & fees
Jan 7 - Jan 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (1007)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transportation Center, this hotel offers peaceful accommodations with an indoor pool. Enjoy the fitness center, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theater.
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
Clare
The price is ₩141,570
₩158,133 total
includes taxes & fees
Jan 9 - Jan 10
9.2 out of 10, Wonderful, (1010)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodations include refrigerators and microwaves. Unwind in the hot tub, swim in the indoor or seasonal outdoor pool, and enjoy complimentary breakfast before exploring nearby attractions.
"Friendly staff, very clean room and super comfy bed"
Linda
The price is ₩146,120
₩163,216 total
includes taxes & fees
Jan 12 - Jan 13
9.2 out of 10, Wonderful, (126)
Explore Glacial Potholes from this welcoming guesthouse offering snowshoeing, sledding, and snowmobiling on site. Enjoy daily housekeeping and easy access to local attractions like the Shelburne Falls Bowling Alley, with Greenfield Station just a 16-minute drive away.
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
Allison
The price is ₩130,013
₩216,010 total
includes taxes & fees
Jan 6 - Jan 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1004)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Center. After working out in the 24-hour fitness center, savor Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"Room was clean and the staff was super friendly and helpful!"
Ethan
The price is ₩150,006
₩167,556 total
includes taxes & fees
Jan 14 - Jan 15
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.
Save an average of 15% on thousands of hotels when you're signed in
Stay near popular Cheshire attractions
Learn more about Cheshire
Get away to romantic Cheshire! Enjoy the skiing, hiking, and local cuisine.
Top Cheshire Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
More cheap stays in Cheshire
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
The price is ₩110,330 per night from Jan 7 to Jan 8
₩110,330
₩123,239 total
Jan 7 - Jan 8
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
