Title: Book The Best Hotels in Windsor, MA for 2025 from CA $106 - Competitive Prices - Expedia.ca [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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Windsor, MA from CA $106 - ![](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 ## Go beyond your typical stay in Windsor Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&travelerType=family_friendly) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&lodging=CABIN) Farm [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&lodging=AGRITOURISM) Pool [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&amenities=HOT_TUB) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&lodging=APARTMENT) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&amenities=PETS) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&lodging=COTTAGE) Condo [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2025-12-01&d1=2025-12-01&endDate=2025-12-03&d2=2025-12-03&lodging=CONDO) ## Check prices for these dates Tonight [Nov 17 - Nov 18](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-17&endDate=2025-11-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 18 - Nov 19](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-18&endDate=2025-11-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 976 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1002) "The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth CA $154 CA $172 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.2/10 Wonderful (1004) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $139 CA $155 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (799) "Easy parking, great community spaces, beautiful decor! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry CA $126 CA $141 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (959) "Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacey CA $124 CA $138 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.8/10 Excellent (2136) "We came here because it was off season, great price, and it had an indoor pool. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monica CA $127 CA $157 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1002) "Very friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $175 CA $251 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG South Lee 9.0/10 Wonderful (783) "Place was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin CA $188 CA $229 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (758) "All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/a866db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/5e762248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel North Adams 8.8/10 Excellent (1004) "Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $172 CA $192 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1001) "I love the ambience - historic and comfortable and excellent food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $209 CA $296 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.4/10 Exceptional (60) "Room was far from spotless but overall good and nice breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah CA $148 CA $165 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/b8545843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/6eebd994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn PLUS+ South Deerfield – Amherst South Deerfield 7.2/10 Good (1004) "Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Max CA $125 CA $140 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (797) "Clean room and staff was super friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuen CA $187 CA $209 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![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) ![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) ![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) ### The Williams Inn Williamstown 9.6/10 Exceptional (541) "Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon CA $268 CA $299 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room (Superior King Bed with a Porch)](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/aaec0515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/ae684309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Extended Stay)](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/c71b3d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Porches Inn at Mass MoCA North Adams 9.4/10 Exceptional (436) "Charming, nice amenities and convenient to museums, fall foliage, hikes." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sonya CA $213 CA $270 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/a6853cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn Lee 9.6/10 Exceptional (372) "We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/be737544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/dd484194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5e45920f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Williamstown Williamstown 8.8/10 Excellent (392) "We really liked the beautiful fire pit and the warm cup of tea after coming home from dinner." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $201 CA $224 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1000) "I have stayed here many times and it is consistently a comfortable, clean and quiet place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanine CA $105 CA $117 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn Express Pittsfield 5.4/10 (809) "Room spotless and staff helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $95 CA $106 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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/2000000/1460000/1457800/1457797/99b13181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites Pittsfield 8.6/10 Excellent (343) "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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candee CA $125 CA $140 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.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.ca/Hotel-Search?startDate=2025-12-01&endDate=2025-12-02®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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels) ## More cheap stays in Windsor ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Red Roof Inn PLUS+ South Deerfield – Amherst 9 Greenfield Rd South Deerfield MA CA $125 CA $140 total Nov 20 - Nov 21 includes taxes & fees 7/10 Good! (1,002 reviews) [](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street, Lee, MA CA $130 CA $145 total Nov 30 - Dec 1 includes taxes & fees 8.2/10 Very Good! (1,003 reviews) [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA CA $139 CA $155 total Dec 15 - Dec 16 includes taxes & fees 9/10 Wonderful! (1,002 reviews) [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd Lenox MA CA $107 CA $120 total Nov 18 - Nov 19 includes taxes & fees 7.4/10 Good! (821 reviews) [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Fairfield Inn & Suites by Marriott Williamstown](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott Williamstown 430 Main St Williamstown MA CA $201 CA $224 total Dec 7 - Dec 8 includes taxes & fees 8.8/10 Excellent! (391 reviews) [](https://expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd Lenox MA CA $156 CA $174 total Nov 23 - Nov 24 includes taxes & fees 9/10 Wonderful! (1,000 reviews) [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Hotels in Windsor with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 11 properties [](https://expedia.ca/4Star-Windsor-Hotels.s40-0-d6005427.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 96 properties [](https://expedia.ca/3Star-Windsor-Hotels.s30-0-d6005427.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 80 properties [](https://expedia.ca/2Star-Windsor-Hotels.s20-0-d6005427.Travel-Guide-Filter-Hotels) ## Recent reviews of Windsor hotels ### Vacation Village in the Berkshires 5/5 Excellent "Just stayed overnight, literally there 12 hours, so was not able to take advantage of any of the amenities, but would definitely come back for a longer stay!" A verified traveller stayed at Vacation Village in the Berkshires Posted 1 day ago [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ### The Yankee, Trademark Collection by Wyndham 5/5 Excellent "Great stay!" A verified traveller stayed at The Yankee, Trademark Collection by Wyndham Posted 2 days ago [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Berkshire Mountain Lodge 5/5 Excellent "The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway " A verified traveller stayed at Berkshire Mountain Lodge Posted 2 days ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ### Red Roof Inn PLUS+ South Deerfield – Amherst 5/5 Excellent "Stop over hotel " A verified traveller stayed at Red Roof Inn PLUS+ South Deerfield – Amherst Posted 3 days ago [](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 5/5 Excellent "The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! " A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel Posted 5 days ago [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 5/5 Excellent "The staff were awesome! Both ladies at the front desk were so nice and accommodating. Would definitely stay there again!" A verified traveller stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG Posted 5 days ago [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ### Hampton Inn & Suites Berkshires-Lenox 5/5 Excellent "Clean, pleasant staff and good breakfast. " A verified traveller stayed at Hampton Inn & Suites Berkshires-Lenox Posted 5 days ago [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ### The Williams Inn 5/5 Excellent "Did not eat breakfast" A verified traveller stayed at The Williams Inn Posted 6 days ago [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ### Berkshires Untold 5/5 Excellent "Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere." A verified traveller stayed at Berkshires Untold Posted 6 days ago [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ## Frequently asked questions ### What's the best place to stay in Windsor? > [Vacation Village in the Berkshires](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information), located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay based on our traveler data. Other good options for your visit to the area are [Hotel Downstreet, an Ascend Collection Hotel](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) and [Berkshire Mountain Lodge](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information). See all available [top hotels](https://www.expedia.ca/Hotel-Search?regionId=6005427), or [vacation rentals in Windsor](https://www.expedia.ca/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals). ### What's the top vacation rental in Windsor? > [Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information): This vacation home rental outside of Windsor is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all [vacation rentals in Windsor](https://www.expedia.ca/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals). ### If I need to cancel my hotel reservation in Windsor, will I receive a refund? > Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by [fully refundable](https://www.expedia.ca/Hotel-Search?regionId=6005427&paymentType=FREE_CANCELLATION) to find flexible hotel deals in Windsor. ### What is staying in Windsor like? > Visitors can enjoy all that Windsor has to offer including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodations to choose from. Find out more about [Windsor](https://www.expedia.ca/Windsor.dx6005427). ### What should I do while I'm visiting Windsor? > Places to visit in the wider area include [Wahconah Falls State Park](https://www.expedia.ca/Wahconah-Falls-State-Park-Dalton.d553248621532665297.Vacation-Attraction), [Crane Museum of Papermaking](https://www.expedia.ca/Crane-Museum-Of-Papermaking-Dalton.d553248621532665296.Vacation-Attraction), and [Mount Greylock State Reservation Visitor Center](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction). You'll also find [Swift River](https://www.expedia.ca/Swift-River-Massachusetts.d681613380051832832.Vacation-Attraction) and [Mount Greylock](https://www.expedia.ca/Mount-Greylock-Adams.d6091829.Vacation-Attraction) in the area. Check out what more to see and do in Expedia's [Windsor guide](https://www.expedia.ca/Windsor.dx6005427). ### What's the seasonal weather like in Windsor? > The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. 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