
Find hotels in Cheshire, MA from ฿2,246
- 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

Harbour House Inn
Harbour House InnCheshire
9.4 out of 10, Exceptional, (53 reviews)
The price is ฿8,246
฿8,716 total
includes taxes & fees
1 Jun - 2 Jun

The Yankee Inn
The Yankee InnLenox
9.2 out of 10, Wonderful, (1,001 reviews)
The price is ฿4,518
฿5,047 total
includes taxes & fees
25 Jun - 26 Jun

Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1,000 reviews)
The price is ฿3,705
฿4,138 total
includes taxes & fees
7 Jun - 8 Jun

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West StockbridgeWest Stockbridge
6.8 out of 10, (1,001 reviews)
The price is ฿2,048
฿2,246 total
includes taxes & fees
31 May - 1 Jun

Blooming Inn
Blooming InnShelburne Falls
9.2 out of 10, Wonderful, (136 reviews)
The price is ฿3,393
฿5,383 total
includes taxes & fees
2 Jun - 3 Jun

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
8.4 out of 10, Very good, (1,001 reviews)
The price is ฿3,675
฿4,104 total
includes taxes & fees
2 Jun - 3 Jun

Cozy Corner Motel
Cozy Corner MotelWilliamstown
9.2 out of 10, Wonderful, (910 reviews)
The price is ฿2,750
฿3,235 total
includes taxes & fees
8 Jun - 9 Jun

Berkshires Untold
Berkshires UntoldLenox
9.0 out of 10, Wonderful, (962 reviews)
The price is ฿4,059
฿4,534 total
includes taxes & fees
3 Jun - 4 Jun

Shaker Mill Inn
Shaker Mill InnWest Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
The price is ฿4,843
฿5,313 total
includes taxes & fees
1 Jun - 2 Jun

The Villager Motel
The Villager MotelWilliamstown
8.8 out of 10, Excellent, (787 reviews)
The price is ฿2,893
฿3,231 total
includes taxes & fees
3 Jun - 4 Jun

Becket Motel
Becket MotelBecket
6.8 out of 10, (61 reviews)
The price is ฿3,088
฿4,538 total
includes taxes & fees
31 May - 1 Jun

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHGPittsfield
9.4 out of 10, Exceptional, (99 reviews)
The price is ฿4,681
฿5,228 total
includes taxes & fees
22 Jun - 23 Jun

The Revival House
The Revival HouseAdams
9.0 out of 10, Wonderful, (32 reviews)
The price is ฿5,383
฿6,013 total
includes taxes & fees
16 Jun - 17 Jun

Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (960 reviews)
The price is ฿4,343
฿5,578 total
includes taxes & fees
29 Jun - 30 Jun

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.2 out of 10, Wonderful, (1,000 reviews)
The price is ฿4,169
฿4,657 total
includes taxes & fees
3 Jun - 4 Jun

Berkshire Travel Lodge
Berkshire Travel LodgeAusterlitz
5.4 out of 10, (467 reviews)
The price is ฿2,135
฿2,392 total
includes taxes & fees
31 May - 1 Jun

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great BarringtonLee
6.4 out of 10, (664 reviews)
The price is ฿2,315
฿2,586 total
includes taxes & fees
10 Jun - 11 Jun

Rodeway Inn
Rodeway InnAdams
7.4 out of 10, Good, (243 reviews)
The price is ฿2,633
฿2,941 total
includes taxes & fees
22 Jun - 23 Jun

Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
7.6 out of 10, Good, (856 reviews)
The price is ฿2,568
฿2,868 total
includes taxes & fees
1 Jun - 2 Jun

Maple Terrace Motel
Maple Terrace MotelWilliamstown
9.6 out of 10, Exceptional, (607 reviews)
The price is ฿3,738
฿4,175 total
includes taxes & fees
9 Jun - 10 Jun
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 wildlife.

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
The price is ฿2,568 per night from 1 Jun to 2 Jun
฿2,568
฿2,868 total
1 Jun - 2 Jun
includes taxes & fees
7.6/10 Good! (856 reviews)










































































