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
17.31 mi from Cheshire, MA, USA
4.35 stars rating. Excellent. 1632 reviews4.35 stars rating. Excellent. 1632 reviews
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Strikethrough Rate:~~$112~~Discounted rate:$106USD/night
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Hotel Downstreet, an Ascend Collection Hotel
40 Main Street,
North Adams, MA, 01247, US
9.82 mi from Cheshire, MA, USA
4.28 stars rating. Excellent. 195 reviews4.28 stars rating. Excellent. 195 reviews
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Strikethrough Rate:~~$175~~Discounted rate:$157USD/night
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Quality Inn Lee - Lenox South
170 Housatonic St,
Lee, MA, 01238, US
18.5 mi from Cheshire, MA, USA
4.24 stars rating. Excellent. 358 reviews4.24 stars rating. Excellent. 358 reviews
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Strikethrough Rate:~~$109~~Discounted rate:$98USD/night
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AWARD WINNER
Quality Inn Great Barrington
372 Main Street,
Great Barrington, MA, 01230, US
27.49 mi from Cheshire, MA, USA
4.33 stars rating. Excellent. 410 reviews4.33 stars rating. Excellent. 410 reviews
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Strikethrough Rate:~~$89~~Discounted rate:$80USD/night
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Econo Lodge Lee - Great Barrington
980 Pleasant Street,
Lee, MA, 01238, US
20.17 mi from Cheshire, MA, USA
3.16 stars rating. Good. 502 reviews3.16 stars rating. Good. 502 reviews
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Strikethrough Rate:~~$69~~Discounted rate:$64USD/night
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Comfort Inn & Suites East Greenbush - Albany
99 Miller Road,
Castleton, NY, 12033, US
26.31 mi from Cheshire, MA, USA
3.99 stars rating. Good. 1815 reviews3.99 stars rating. Good. 1815 reviews
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Strikethrough Rate:~~$124~~Discounted rate:$112USD/night
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Rodeway Inn
99 Howland Ave,
Adams, MA, 01220, US
6.66 mi from Cheshire, MA, USA
No Reviews YetNo Reviews Yet
Coming soonStart booking Jan 16, 2026
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Good to know

Top-Rated hotels

7 hotels in Cheshire

Highest Price

$157

Lowest Price

$64

Avg. rating

3.5 (4912 reviews)