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
Check prices for these dates
Top 10 trending Windsor hotels

Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
7.2 out of 10, Good, (1000)
The price is €103
includes taxes & fees
1 Sept - 2 Sept

Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
9.2 out of 10, Wonderful, (1000)
The price is €138
includes taxes & fees
1 Sept - 2 Sept

Blooming Inn
Blooming Inn
9.2 out of 10, Wonderful, (110)
The price is €138
includes taxes & fees
14 Sept - 15 Sept

The Williams Inn
The Williams Inn
9.6 out of 10, Exceptional, (485)
The price is €224
includes taxes & fees
7 Sept - 8 Sept

Willows Motel Williamstown
Willows Motel Williamstown
9.0 out of 10, Wonderful, (937)
The price is €85
includes taxes & fees
1 Sept - 2 Sept

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.2 out of 10, Wonderful, (1003)
The price is €129
includes taxes & fees
8 Sept - 9 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

Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
More cheap stays in Windsor
More cheap stays in Windsor

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
The price is €68 per night from 31 Aug to 1 Sept
€68
31 Aug - 1 Sept
includes taxes & fees
5.2/10 (766 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
- Appalachian Mountains Hotels
- Hancock Hotels
- Becket Hotels
- Hudson River Valley Hotels
- Adams Hotels
More top Windsor Hotels
Expedia's Latest Trends
Hotels
Cars
Activities