Book Top Rated Hotels in Cheshire, MA | Choice Hotels

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel Street,
Lee, MA, 01238, US
27.85 km from Cheshire, MA, USA
4.35 stars rating. Excellent. 1620 reviews4.35 stars rating. Excellent. 1620 reviews
Book Now & Save 5%
Strikethrough Rate:~~$125~~Discounted rate:$119USD/night
Member Rate
See Availability
Quality Inn
170 Housatonic St,
Lee, MA, 01238, US
29.78 km from Cheshire, MA, USA
4.24 stars rating. Excellent. 358 reviews4.24 stars rating. Excellent. 358 reviews
Book Now & Save 10%
Strikethrough Rate:~~$109~~Discounted rate:$98USD/night
Member Rate
See Availability
Hotel Downstreet, an Ascend Collection Hotel
40 Main Street,
North Adams, MA, 01247, US
15.8 km from Cheshire, MA, USA
4.27 stars rating. Excellent. 182 reviews4.27 stars rating. Excellent. 182 reviews
Book Now & Save 10%
Strikethrough Rate:~~$176~~Discounted rate:$158USD/night
Member Rate
See Availability
Quality Inn
372 Main Street,
Great Barrington, MA, 01230, US
44.24 km from Cheshire, MA, USA
4.32 stars rating. Excellent. 401 reviews4.32 stars rating. Excellent. 401 reviews
Book Now & Save 10%
Strikethrough Rate:~~$99~~Discounted rate:$89USD/night
Member Rate
See Availability
Econo Lodge Lee - Great Barrington
980 Pleasant Street,
Lee, MA, 01238, US
32.46 km from Cheshire, MA, USA
3.15 stars rating. Good. 499 reviews3.15 stars rating. Good. 499 reviews
Book Now & Save 7%
Strikethrough Rate:~~$68~~Discounted rate:$63USD/night
Member Rate
See Availability
Comfort Inn & Suites East Greenbush - Albany
99 Miller Road,
Castleton, NY, 12033, US
42.34 km from Cheshire, MA, USA
3.99 stars rating. Good. 1801 reviews3.99 stars rating. Good. 1801 reviews
Book Now & Save 10%
Strikethrough Rate:~~$125~~Discounted rate:$112USD/night
Member Rate
See Availability

Change your dates to book properties below.

Rodeway Inn
99 Howland Ave,
Adams, MA, 01220, US
10.71 km from Cheshire, MA, USA
No Reviews YetNo Reviews Yet
Coming soonStart booking 16 Jan 2026
See Availability

Other Cheshire searches

All Hotels in Cheshire

Boutique Hotels in Cheshire

Hotel Deals in Cheshire

Extended Stay Hotels in Cheshire

Pet Friendly Hotels in Cheshire

Good to know

Top-Rated hotels

7 hotels in Cheshire

Highest Price

$158

Lowest Price

$63

Avg. rating

3.5 (4861 reviews)