Find hotels in Windsor, MA from ¥11,947
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Our top choices for Windsor hotels

Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – AmherstSouth Deerfield
7.2 out of 10, Good, (1000)
The price is ¥13,332
¥14,892 total
includes taxes & fees
Jan 11 - Jan 12, 2026

Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1000)
The price is ¥11,910
¥13,304 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The price is ¥12,351
¥21,437 total
includes taxes & fees
Jan 11 - Jan 12, 2026

9.2 out of 10, Wonderful, (1000)
The price is ¥14,448
¥16,139 total
includes taxes & fees
Jan 4 - Jan 5, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1000)
The price is ¥15,641
¥17,471 total
includes taxes & fees
Jan 15 - Jan 16, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (998)
The price is ¥13,754
¥15,363 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

The Yankee, Trademark Collection by Wyndham
10/10 Excellent
More cheap stays in Windsor

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
The price is ¥12,319 per night from Dec 28 to Dec 29
¥12,319
¥13,760 total
Dec 28 - Dec 29
includes taxes & fees
7.4/10 Good! (827 reviews)
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