Find Cheap Hotels in Windsor, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Windsor Cheap Hotels
Tonight
Sep 18 - Sep 19Tomorrow
Sep 19 - Sep 20This weekend
Sep 18 - Sep 20Next weekend
Sep 25 - Sep 27Our top choices for Windsor cheap hotels
NT$1,975
NT$2,206 total
includes taxes & fees
Sep 20 - Sep 21
2. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Debra
NT$3,476
NT$3,883 total
includes taxes & fees
Oct 19 - Oct 20
NT$2,532
NT$3,539 total
includes taxes & fees
Oct 1 - Oct 2
NT$2,513
NT$2,807 total
includes taxes & fees
Sep 20 - Sep 21
5. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Joe
NT$3,374
NT$3,768 total
includes taxes & fees
Oct 18 - Oct 19
NT$3,700
NT$4,132 total
includes taxes & fees
Sep 22 - Sep 23
NT$5,281
NT$5,900 total
includes taxes & fees
Sep 20 - Sep 21
NT$2,697
NT$3,012 total
includes taxes & fees
Sep 20 - Sep 21
View all properties
Top Windsor Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Our family has been going there for years. Thr rooms are spacious and amenities work well for us."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"The on site, Indian restaurant was excellent. The staff was very nice, the food was great. The breakfast buffet in the morning, was basic, but very good.. I would definitely stay here again if I was in the area."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
Frequently asked questions
Explore a world of travel with Expedia
- Hinsdale Hotels
- Historic Hotels in Richmond
- Family Hotels in Greenfield
- Hotels near Mount Greylock
- Golf Hotels in Lanesborough
- Pet-Friendly Hotels in Pittsfield
- Hotels with smoking rooms in Western Massachusetts
- Hotel Wedding Venues Hotels in Stockbridge
- Hotel Wedding Venues Hotels in Williamstown
- Hotels near Williams College
- Romantic Hotels in Lenox
- Boutique Hotels in North Adams
- Hotels near Berkshire East Ski Resort
- Golf Hotels in Pittsfield
- Hotels with an Indoor Pool in Lenox
- Williamstown Hotels
- 5 Star Hotels in Becket
- Hotels with an Indoor Pool in Pittsfield
- Historic Hotels in Lenox
- Guest Houses in Pittsfield Intermodal Transportation Center
- 4 Star Hotels in Charlemont
- Romantic Hotels in Northampton
- Cheap Hotels in Pittsfield
- Golf Hotels in Williamstown
- Hotels near Herman Melville's Arrowhead
- Hotels with Hot Tubs in Lee
- Ski Hotels in Stockbridge
- Pet-Friendly Hotels in Western Massachusetts
- Hotels near Bousquet Ski Area
- Hotels with smoking rooms in Lee
- Hotels near Bas Ridge Golf Course
- Cabin Rentals in North Adams
- Pet-Friendly Hotels in Lee
- Hotels with a Pool in Stockbridge
- Resorts & Hotels with Spas in Hancock
- Winery Hotels in Western Massachusetts
- Resorts & Hotels with Spas in Deerfield
- 3 Star Hotels in Goshen
- Hotels near Hawley Bog Preserve
- Gay friendly Hotels in Williamstown
- Lodges in Cummington
- 4 Star Hotels in Hawley
- Hotels with Bars in North Adams
- Historic Hotels in Greenfield
- Goshen Hotels
- Hotels with Bars in Pittsfield
- Pittsfield Hotels
- Hotels with Bars in South Deerfield
- Hotels near Guido's Marketplace
- 3 Star Hotels in Lanesborough
- Flights from Pittsfield Municipal
- Flights from North Adams
- Flights from Houston (HOU) to Pittsfield (PSF)
- Flights to North Adams
- Flights from Bangor (BGR) to Pittsfield (PSF)
- Flights from Watertown (ART) to Pittsfield (PSF)
- Flights to Williamstown
- Flights from Pittsfield
- Flights from Portsmouth (PSM) to Pittsfield (PSF)
- Flights to Shelburne Falls
- Flights from Williamstown
- Flights from Asheville (AVL) to Pittsfield (PSF)
- Flights from Chester
- Flights from Washington (DCA) to Pittsfield (PSF)
- Flights from Charleston (CRW) to Pittsfield (PSF)
- Flights from Sydney (SYD) to Pittsfield (PSF)
- Flights from Louisville (LOU) to Pittsfield (PSF)
- Visit Ashfield
- Chesterfield Gorge
- Williamstown Theatre Festival
- Canoe Meadows Wildlife Sanctuary
- Hawley Bog Preserve
- Williams College Museum of Art
- Crane Museum of Papermaking
- Kushi Institute
- Visit Charlemont
- Visit Lanesborough
- Lenox Mountain
- Massachusetts Museum of Contemporary Art
- North Adams Public Library
- Visit Buckland
- Visit Middlefield
- Ashfield Lake
- Visit North Adams
- 62 Center for Theater and Dance
- Visit Williamstown
- Bissell Covered Bridge
- Mount Greylock State Reservation Visitor Center
- Visit Hancock
- Charlemont Federated Church
- Visit Lee
- Visit Dalton
- Bousquet Ski Area