Title: The Best 4 Star Hotels in Windsor, MA from $122 | 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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Windsor 4 Star Hotels Tonight [Feb 11 - Feb 12](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-11&endDate=2026-02-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 12 - Feb 13](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-12&endDate=2026-02-13&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-13&endDate=2026-02-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-20&endDate=2026-02-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor 4-star hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn [](https://www.expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (573 reviews) "Very pleasant and relaxing place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) steve $189 nightly $212 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/4092a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d652d2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED | Individually furnished, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (355 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn $109 nightly $122 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/870ad54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (292 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny $149 nightly $166 total Mar 14 - Mar 15 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Room #10 Queen's Cottage | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/ae0cb55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.com/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (135 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher $269 nightly $300 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/9d4b10ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/07d85fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/ee47037f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/3c58b600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seven Hills Inn [](https://www.expedia.com/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) Lenox 7.8/10 Good (467 reviews) "Great location, nice breakfast and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.com/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.com/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah $335 nightly $374 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.com/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $397 nightly $444 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/84d1c1bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/32a90503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/32cb12aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/95ce4320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### General Williams Estate House Lenox/Stockbridge [](https://www.expedia.com/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) Stockbridge 9.8/10 Exceptional (115 reviews) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna T. [](https://www.expedia.com/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rosalyn Elkan Suite, Cottage | Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/01b23076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/f5dca788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.com/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (43 reviews) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby $219 nightly $245 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/c5b973e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/b5bad44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge [](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) Lee 9.8/10 Exceptional (99 reviews) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven $251 nightly $280 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/0eb6e44a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/f210c5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/7ddf77a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/00d33bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garden Gables Inn [](https://www.expedia.com/Lenox-Hotels-Garden-Gables-Inn.h893627.Hotel-Information) Lenox 9.2/10 Wonderful (57 reviews) "Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john [](https://www.expedia.com/Lenox-Hotels-Garden-Gables-Inn.h893627.Hotel-Information) ![](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%2F4Star-Windsor-Hotels.s40-0-d6005427.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Windsor-Hotels.s40-0-d6005427.Travel-Guide-Filter-Hotels) ## Top Windsor Hotel Reviews ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff." [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## Find out more about Windsor ## Windsor Four Star Hotel Information When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Windsor, Massachusetts are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Windsor 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service. Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Windsor. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Windsor, Massachusetts, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop. Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Windsor hotels offer everything your heart desires. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Windsor? > - Search for the lowest price from $122 ### What's the difference between 5-star and 4-star hotels in Windsor? ### Does Windsor have any 4-star all-inclusive resorts? ## 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) - [Savoy Hotels ](https://www.expedia.com/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Cabin Rentals in Savoy ](https://www.expedia.com/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [B&B in Savoy ](https://www.expedia.com/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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