Book Boutique Hotels in Windsor, MA

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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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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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:~~$129~~Discounted rate:$116USD/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 Hadley - Amherst
400 Russell Street,
Hadley, MA, 01035, US
4.51 stars rating. Excellent. 602 reviews
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Strikethrough Rate:~~$149~~Discounted rate:$132USD/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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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:~~$75~~Discounted rate:$70USD/night
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Quality Inn & Suites Northampton- Amherst
117 Conz Street,
Northampton, MA, 01060, US
3.52 stars rating. Good. 1109 reviews
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Strikethrough Rate:~~$144~~Discounted rate:$130USD/night
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New Englander Inn Bennington
220 Northside Dr,
Bennington, VT, 05201, US
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Coming soonStart booking 05 Jun 2026
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