Title: Windsor Travel Guide: Best of Windsor, Massachusetts Travel 2026 | Expedia.co.uk [Hotels in Windsor](https://expedia.co.uk/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Holiday Rentals in Windsor](https://expedia.co.uk/Windsor-Holiday-Rentals.d6005427.Travel-Guide-HolidayRentals)[Windsor Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windsor.d6005427.Car-Hire-Guide)[Windsor Holidays](https://expedia.co.uk/Windsor.d6005427.Holidays-City-Breaks) # Windsor Travel Guide ## Tourist Guide ## Visit Windsor - Top hotels in Windsor - Top Holiday Rentals in Windsor ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA £95 19 Jan - 20 Jan includes taxes & fees Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ... 8.6/10 Excellent! (2,205 reviews) The amount of space and super comfortable bed was such a pleasure! Reviewed on 13 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005427) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA £104 2 Feb - 3 Feb includes taxes & fees Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ... 8.6/10 Excellent! (1,004 reviews) Staff was pleasant and helpful, room spacey and all immaculate . Reviewed on 11 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=6005427) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG One West Street Pittsfield MA £81 23 Jan - 24 Jan includes taxes & fees Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ... 8/10 Very Good! (1,004 reviews) Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ... Reviewed on 7 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true®ionId=6005427) [See all 959 properties in Windsor](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=16%2F01%2F2026&endDate=17%2F01%2F2026®ionId=6005427) 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. ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ... 8.6/10 Excellent! (2,205 reviews) The amount of space and super comfortable bed was such a pleasure! Reviewed on 13 Jan 2026 [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huttopia Berkshires 312 Kittle Rd Williamstown MA Stay at this campsite in Williamstown. Enjoy free parking, breakfast (surcharge) and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ... 10/10 Exceptional! (7 reviews) Healthy food too! Reviewed on 20 Oct 2025 [](https://expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jiminy Peak Mountain Resort 37 Corey Rd Hancock MA Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ... 8.2/10 Very Good! (989 reviews) This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ... Reviewed on 5 Oct 2025 [](https://expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) [See all properties in Windsor](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6005427&sort=VACATION_RENTAL) 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. ## Check Windsor hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-01-15&endDate=2026-01-16)[15 Jan - 16 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-01-15&endDate=2026-01-16) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-01-16&endDate=2026-01-17)[16 Jan - 17 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-01-16&endDate=2026-01-17) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026)[16 Jan - 18 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026)[23 Jan - 25 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026) ## Cities near Windsor ![Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cheshire - Cities near Windsor - Places of interest [Cummington](https://expedia.co.uk/Cummington.dx183324)[Cheshire](https://expedia.co.uk/Cheshire.dx6005398) - [Tanglewood Music Center ](https://expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.Attraction) - [Williams College ](https://expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Green Mountain National Forest ](https://expedia.co.uk/Green-Mountain-National-Forest-Vermont.d6115904.Attraction) - [Norman Rockwell Museum ](https://expedia.co.uk/Norman-Rockwell-Museum-Stockbridge.d6091839.Attraction) - [Ventfort Hall Mansion and Gilded Age Museum ](https://expedia.co.uk/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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