Find hotels in Windsor, MA from ¥11,931
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Our top choices for Windsor hotels

9.2 out of 10, Wonderful, (1000)
The price is ¥11,730
¥13,103 total
includes taxes & fees
Dec 24 - Dec 25

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 ¥15,761
¥17,605 total
includes taxes & fees
Dec 21 - Dec 22

8.8 out of 10, Excellent, (2170)
The price is ¥16,193
¥19,796 total
includes taxes & fees
Dec 17 - Dec 18
The price is ¥17,077
¥19,076 total
includes taxes & fees
Dec 16 - Dec 17

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (984)
The price is ¥14,437
¥16,127 total
includes taxes & fees
Dec 14 - Dec 15

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHGSouth Lee
9.0 out of 10, Wonderful, (798)
The price is ¥18,782
¥24,024 total
includes taxes & fees
Dec 14 - Dec 15
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 Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
More cheap stays in Windsor

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
The price is ¥11,730 per night from Dec 24 to Dec 25
¥11,730
¥13,103 total
Dec 24 - Dec 25
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
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Stay near popular Windsor attractions
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Tanglewood Music Center
- Hotels near Green Mountain National Forest
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Williams College
- Hotels near Mount Greylock
- Hotels near Jacob's Pillow
- Hotels near Colonial Theater
- Hotels near Mount Greylock State Reservation Visitor Center
- Hotels near Hancock Shaker Village
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