Title: Top Preferred in Windsor, MA - Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d6005427.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check prices for these dates Tonight [Mar 9 - Mar 10](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-09&endDate=2026-03-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 10 - Mar 11](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-10&endDate=2026-03-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor Preferred ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/9f24830b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/192c9e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/27d5352c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/c7a35aa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Orchards Hotel [](https://www.expedia.com/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information) Williamstown 8.6/10 Excellent (442 reviews) "A little dated. Restaurant shut down for renovations, disappointing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler [](https://www.expedia.com/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25®ionId=6005427&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels-Preferred.0-0-d6005427--bPreferred.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels-Preferred.0-0-d6005427--bPreferred.Travel-Guide-Filter-Hotels) ## Top Windsor Hotel Reviews ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "In the process of remodeling, but my room which was already renovated was very nice, as was the breakfast room. " [](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 4/10 Poor "The property was clean but the beds were very uncomfortable. They need to replace the mattresses." [](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "This was great. I did not really need the kitchen for my stay but for future planning this wil be great! Plenty of room in the living area. Bed was comfortable. Just beautiful " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Great place in Williamstown. Near ski resort." [](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 8/10 Good "This place is okay. The view is stellar, but the hotel itself is average. It did the job. " [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "This area is really starting to build up. There is a small ski area. An Italian restaurant and 110 grill right on that road. About 15 min away Applebees. A lot of pizza and Mexican. Winter not only is there skiing there are a lot of snowmobile trails. Summer there are water falls you can see. Tubing you can do. The mountains are beautiful. Quiet and relaxing. " [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 6/10 Okay "Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good look or feel for those staying there. Maybe in six months or a year down the line, hotel will come back to its glory. Today still needs lots of work. " [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_y.jpg) ### Huttopia Berkshires 10/10 Excellent "Excelente servicio " [](https://expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Room was awesome and very clean " [](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Hotels.0-l553248621532665297-0.Travel-Guide-Filter-Hotels) - 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