Book Top Rated Hotels in Cheshire, MA

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Hotel Downstreet, an Ascend Collection Hotel
40 Main Street,
North Adams, MA, 01247, US
4.32 stars rating. Excellent. 252 reviews
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Strikethrough Rate:~~$164~~Discounted rate:$147USD/night
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The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel Street,
Lee, MA, 01238, US
4.35 stars rating. Excellent. 1661 reviews
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Strikethrough Rate:~~$130~~Discounted rate:$117USD/night
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Rodeway Inn
99 Howland Ave,
Adams, MA, 01220, US
3.33 stars rating. Good. 6 reviews
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Strikethrough Rate:~~$79~~Discounted rate:$71USD/night
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Quality Inn Lee - Lenox South
170 Housatonic St,
Lee, MA, 01238, US
4.26 stars rating. Excellent. 380 reviews
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Strikethrough Rate:~~$119~~Discounted rate:$107USD/night
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AWARD WINNER
Quality Inn Great Barrington
372 Main Street,
Great Barrington, MA, 01230, US
4.36 stars rating. Excellent. 447 reviews
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Strikethrough Rate:~~$89~~Discounted rate:$80USD/night
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Comfort Inn & Suites East Greenbush - Albany
99 Miller Road,
Castleton, NY, 12033, US
4 stars rating. Very Good. 1870 reviews
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Strikethrough Rate:~~$169~~Discounted rate:$152USD/night
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Econo Lodge Lee - Great Barrington
980 Pleasant Street,
Lee, MA, 01238, US
3.18 stars rating. Good. 508 reviews
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Strikethrough Rate:~~$89~~Discounted rate:$83USD/night
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New Englander Inn Bennington
220 Northside Dr,
Bennington, VT, 05201, US
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Coming soonStart booking Jun 05, 2026
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