Title: 4 Stars Hotels in Windsor, Massachusetts from CA $152 - Find Cheap Windsor Hotels With 4 Stars | Expedia.ca [Windsor Travel Guide](https://expedia.ca/Windsor.dx6005427)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d6005427.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d6005427.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Windsor, Massachusetts from CA $152 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](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 [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.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 Williamstown 9.6/10 Exceptional (524) "Nice place to stay for a wedding " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $262 CA $292 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/c81c0732.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/d28e6aa1.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/2000000/1460000/1457800/1457797/99b13181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites Pittsfield 8.8/10 Excellent (326) "The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Candee CA $136 CA $152 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/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) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/21cb26fe.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) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn Lee 9.6/10 Exceptional (285) "Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $251 CA $295 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.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) ![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 (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 Wonderful (107) "Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $435 CA $526 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.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) ![Manor House King](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/bb81fbdc.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) ### Seven Hills Inn Lenox 7.8/10 Good (467) "Great location, nice breakfast and clean rooms" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/2ae49251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/461d5056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/d0befd42.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 Stockbridge 9.8/10 Exceptional (110) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna T. [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) ![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](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #10 Queen's Cottage | Private kitchen](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/bbf9b83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/2d151170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B Lee 10/10 Exceptional (131) "The inn has an excellent location and amenities." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $479 CA $535 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/edd6aeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gilded Stage in the Mainhouse](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/76b1fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Interior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/44792ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge Lee 9.8/10 Exceptional (98) "Well-run and elegant property. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $495 CA $581 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/8d18b6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marion Slocomb Suite, Cottage](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cd8fcdd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/175edf77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn Lenox 9.0/10 Wonderful (42) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby CA $416 CA $464 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/2028495b.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) ![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 Lenox 10/10 Exceptional (73) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $728 CA $814 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.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) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/64845fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/ac720fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/2e052a7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garden Gables Inn Lenox 9.2/10 Wonderful (57) "Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) john [](https://www.expedia.ca/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.ca/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.ca/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](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Lovely clean room with a fabulous shower. Tea/coffee available 24 hours with a choice of milks which is great. Refillable glass bottle in the room to collect fresh water which meant no plastic bottles. Plenty of parking, cosy lobby and restaurant food excellent. " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## Find out more about Windsor If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Windsor are calling your name. Known for providing first-rate service in amazing locations, each of the Windsor 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Windsor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Windsor, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Windsor hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Windsor? > With Expedia's handy filter tool, locking in a terrific deal on a 4-star hotel in Windsor just got simpler. Start by entering your chosen travel dates and length of your stay. Then sort the results by price and pick the option that best suits your budget and style. > > > > - Search for the lowest price from CA $152 ### What's the difference between 5-star and 4-star hotels in Windsor? > If you decide to book a stay at a 4-star hotel in Windsor, you'll typically find lots of conveniences to keep you relaxed, such as a restaurant, gym and pool. You can look forward to excellent service and upmarket accommodations. Go for a 5-star hotel and you'll get a few more perks — think concierge assistance, on-site spas and nightly turndown services. You'll most likely get extra amenities and premium services at a 5-star getaway, though both are fabulous options for luxury travellers. ### Does Windsor have any 4-star all-inclusive resorts? > Finding vacation bliss in Windsor is as easy as entering in your destination and dates, and selecting our "All inclusive" filter. 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