Windsor Hotels
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Go beyond your typical stay in Windsor
Farm
Resort
Check prices for these dates
Top 10 trending Windsor hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
9.0 out of 10, Wonderful, (1002)
The price is €121
includes taxes & fees
1 Sept - 2 Sept

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.0 out of 10, Wonderful, (1005)
The price is €119
includes taxes & fees
21 Sept - 22 Sept

Berkshires Untold
Berkshires Untold
9.0 out of 10, Wonderful, (692)
The price is €153
includes taxes & fees
1 Sept - 2 Sept

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1968)
The price is €111
includes taxes & fees
7 Sept - 8 Sept

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
8.8 out of 10, Excellent, (1003)
The price is €137
includes taxes & fees
22 Sept - 23 Sept

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
9.0 out of 10, Wonderful, (1002)
The price is €155
includes taxes & fees
2 Sept - 3 Sept
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.
Save an average of 15% on thousands of hotels when you're signed in
Learn more about Windsor
Explore Windsor: its dining and more!
Top Windsor Hotel Reviews

The Constance by the Lenox Collection
10/10 Excellent
More cheap stays in Windsor
More cheap stays in Windsor

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is €75 per night from 1 Sept to 2 Sept
€75
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (785 reviews)
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Near an Airport
Hotels Near Windsor, Massachusetts
- New England Hotels
- Upstate New York Hotels
- Lenox Hotels
- The Berkshires Hotels
- Williamstown Hotels
- Pittsfield Hotels
- Northampton Hotels
- Great Barrington Hotels
- Hudson Valley Hotels
- Bennington Hotels
- Stockbridge Hotels
- Lee Hotels
- North Adams Hotels
- Greenfield Hotels
- Westfield Hotels
- Hancock Hotels
- Appalachian Mountains Hotels
- Hudson River Valley Hotels
- Becket Hotels
- Adams Hotels
More top Windsor Hotels
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- The Constance by the Lenox Collection
- Best Western Plus Berkshire Hills Inn & Suites
- The Porches Inn at Mass MoCA
- Quality Inn
- Hotel On North
- Jiminy Peak Mountain Resort
Expedia's Latest Trends
Hotels
Cars
Activities