Title: Windsor Chalets from CA $108 | Expedia.ca [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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Windsor from CA $108 - ![](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 prices for these dates Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windsor Chalets No exact matches found, but these alternatives could be just right ## Recommended hotels in Windsor ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.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) ![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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/de7f46bc.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) ![Suite, 1 King Bed (Smoke Free)](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/ec8c0b54.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.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) ![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/a25612d3.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) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank 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) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn West Stockbridge 9.6/10 Exceptional (435) "Nice place, easy check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $140 CA $154 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/78a9a11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/eba22fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blooming Inn Shelburne Falls 9.2/10 Wonderful (118) "When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) christian CA $102 CA $183 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.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) ![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) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.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) ### 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/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/f1aeba62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.6/10 Exceptional (10) "Very friendly with dog. No complaints with accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lilian CA $189 CA $211 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/568a1b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/2c0ca8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/488c62c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/6203d3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villager Motel Williamstown 8.8/10 Excellent (761) "It's very good for stay over" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frances CA $97 CA $108 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7c9905b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/5062d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel Williamstown 9.2/10 Wonderful (881) "Clean, Great Staff, Quiet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john CA $105 CA $124 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/483e190d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/d1430bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Lee 7.6/10 Good (410) "Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $120 CA $134 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox Lenox 7.6/10 Good (824) "Staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $107 CA $120 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/c64cd286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/9d6fa2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/52ce390c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel Williamstown 9.6/10 Exceptional (584) "Pool, fire pit, grounds and staff were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy CA $139 CA $155 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/05418243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/9aabb83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/b5e2455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee 8.4/10 Very good (1001) "Clean room and good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $130 CA $145 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.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) ![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) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.4/10 Exceptional (60) "Very clean room, courteous staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey 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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/321c91e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/adbcecbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/1d55e99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/2acfd77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In town, newly remodeled studio with private balcony Shelburne Falls 10/10 Exceptional (119) "Lovely apartment, perfect for a short getaway for city slickers. Close to town. The apartment was great, came well-equipped and everything was as described. The deck was lovely to spend a slow morning having breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan N. CA $133 CA $219 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/b8eb795a.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) ![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) ![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/41222353.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) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/9f0c8245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/f6ede23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel Williamstown 9.4/10 Exceptional (311) "It was clean and in a convenient location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $112 CA $125 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/b51475ef.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) ### 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) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c07737f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/6dc4b11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Inn Pittsfield 7.8/10 Good (838) "This property has a mid century motel look from the street but the rooms have been recently upgraded and are fully modern inside. A great value and comfortable place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip CA $103 CA $116 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.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&lodging=CHALET&sort=RECOMMENDED&openPlayBack=true) ## Find vacation rentals that suit your style Apartments [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=APARTMENT) Cabins [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=CABIN) Cottages [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=COTTAGE) Condos [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=CONDO) Villas [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=VILLA) Private vacation homes [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=VACATION_HOME) Chalets [](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=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=CHALET) ![](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-Chalets.d6005427-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Chalets.d6005427-aaChalets.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ### Vacation Village in the Berkshires 10/10 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!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Berkshire Mountain Lodge 10/10 Excellent "The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ### Red Roof Inn PLUS+ South Deerfield – Amherst 10/10 Excellent "Stop over hotel " [](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 10/10 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! " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "The staff were awesome! Both ladies at the front desk were so nice and accommodating. Would definitely stay there again!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Clean, pleasant staff and good breakfast. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ### The Williams Inn 10/10 Excellent "Did not eat breakfast" [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ### Berkshires Untold 10/10 Excellent "Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere." [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ## Find out more about Windsor ## Windsor Chalets information | Number of reviews | 13,026 | | --- | --- | | Accommodation | 4 Chalets | | Lowest Price | CA $108 | | Highest Price | CA $219 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Vacation Rental - More ways to book - [Beach Hotel Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Beach-Hotel.0-0-d6005393-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Cheap-Hotels.0-0-d6005393-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Historic-Hotel.0-0-d6005393-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Mountain-Hotels.0-0-d6005393-tMountainHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Spa-Hotel.0-0-d6005393-tSpaHotel.Travel-Guide-Filter-Hotels) - 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