Book Boutique Hotels in Cheshire, MA | Choice Hotels

Change your dates to book properties below.

Quality Inn
372 Main Street,
Great Barrington, MA, 01230, US
44.24 km from Cheshire, Massachusetts, USA
4.33 stars rating. Excellent. 402 reviews4.33 stars rating. Excellent. 402 reviews
Sold outfor your selected dates
See Availability
Hotel Downstreet, an Ascend Collection Hotel
40 Main Street,
North Adams, MA, 01247, US
15.8 km from Cheshire, Massachusetts, USA
4.27 stars rating. Excellent. 182 reviews4.27 stars rating. Excellent. 182 reviews
Sold outfor your selected dates
See Availability
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel Street,
Lee, MA, 01238, US
27.85 km from Cheshire, Massachusetts, USA
4.35 stars rating. Excellent. 1621 reviews4.35 stars rating. Excellent. 1621 reviews
Sold outfor your selected dates
See Availability
Econo Lodge Lee - Great Barrington
980 Pleasant Street,
Lee, MA, 01238, US
32.46 km from Cheshire, Massachusetts, USA
3.15 stars rating. Good. 500 reviews3.15 stars rating. Good. 500 reviews
Sold outfor your selected dates
See Availability
Quality Inn
170 Housatonic St,
Lee, MA, 01238, US
29.78 km from Cheshire, Massachusetts, USA
4.24 stars rating. Excellent. 358 reviews4.24 stars rating. Excellent. 358 reviews
Sold outfor your selected dates
See Availability
Comfort Inn & Suites East Greenbush - Albany
99 Miller Road,
Castleton, NY, 12033, US
42.34 km from Cheshire, Massachusetts, USA
3.99 stars rating. Good. 1802 reviews3.99 stars rating. Good. 1802 reviews
Sold outfor your selected dates
See Availability
Rodeway Inn
99 Howland Ave,
Adams, MA, 01220, US
10.71 km from Cheshire, Massachusetts, USA
No Reviews YetNo Reviews Yet
Coming soonStart booking 16 Jan 2026
See Availability

Other Cheshire searches

All Hotels in Cheshire

Hotel Deals in Cheshire

Extended Stay Hotels in Cheshire

Pet Friendly Hotels in Cheshire

Top Rated Hotels in Cheshire

Good to know

Boutique hotels

7 hotels in Cheshire

Avg. rating

3.5 (4865 reviews)