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 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=DX_SPRING_PROMO_6005427) - Top hotels in Windsor - Top Holiday Rentals in Windsor ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA £89 8 Mar - 9 Mar 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 ... 8.8/10 Excellent! (2,285 reviews) Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ... Reviewed on 7 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005427) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA £98 31 Mar - 1 Apr 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 ... 8.8/10 Excellent! (1,005 reviews) For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options. Reviewed on 5 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=6005427) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA £105 1 Apr - 2 Apr includes taxes & fees Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ... 9/10 Wonderful! (869 reviews) The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ... Reviewed on 6 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005427) [See all 986 properties in Windsor](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=08%2F03%2F2026&endDate=09%2F03%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/db44d375_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 ... 8.8/10 Excellent! (2,285 reviews) Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ... Reviewed on 7 Mar 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 ... [](https://expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Ponds at Foxhollow 3 Foxhollow Drive Route 7 Lenox MA Stay at this condo in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions Tanglewood Music Center and The Mount are located ... 8.6/10 Excellent! (141 reviews) I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ... Reviewed on 9 Feb 2026 [](https://expedia.co.uk/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.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=2026-03-07&endDate=2026-03-08)[7 Mar - 8 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-07&endDate=2026-03-08) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-08&endDate=2026-03-09)[8 Mar - 9 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-08&endDate=2026-03-09) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026)[13 Mar - 15 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026) ## Cities near Windsor ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.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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