Title: Book the Best Cheshire Ski Hotels in 2025 from CA $93 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d183057.Destination-Travel-Guides) ![Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Ski Hotels in Cheshire, CT from CA $93 - ![](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 Cheshire Ski Hotels Tonight [Nov 27 - Nov 28](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire Ski Hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/e1028a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/24fc1ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/8d58fa7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Waterbury Downtown Waterbury 8.4/10 Very good (1055) "Staff was great. Everything was wonderful!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nuri CA $94 CA $108 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/f60a5e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/d045ec83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/ec5a48cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG Southington 8.6/10 Excellent (1157) "Room was clean, hotel was quiet in a good location, continental breakfast had good variety. Would definitely stay here again. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Angela CA $128 CA $147 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14000/13976/25cacd88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/14000/13976/3f5fc976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/14000/13976/1c60af2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14000/13976/43259728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Cromwell - Middletown Cromwell 6.6/10 (1003) "Nice room for our three night stay. Very clean and friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie CA $81 CA $93 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hartford-Hotels-Quality-Inn-Cromwell-Middletown.h13976.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/ec875b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/eff2fea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/1f9e04f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Middletown Washington Street Historic District 9.0/10 Wonderful (534) "Clean room, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katharine CA $196 CA $254 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/e12904c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/w1703h1271x0y0-b305e0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/44e097e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Cheshire - Southington by IHG Southington 8.2/10 Very good (1008) "Great stay can’t complain" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $156 CA $180 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/e63c41d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/894da154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d9f37f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Avon Old Farms Hotel Avon 8.4/10 Very good (1010) "Very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alvero CA $157 CA $211 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/58bf94a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/3251646a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/c7c394d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/24bb1a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Milford Milford 7.8/10 Good (1008) "Pet friendly, wonderful staff, clean comfortable, secure" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan CA $128 CA $147 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-Milford.h13007.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/fd0bf8f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/96d5810c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/5802b8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/e8c6e002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Southington Southington 7.2/10 Good (1006) "Loved the room decor and cleanliness " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo CA $119 CA $137 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Southington.h49987.Hotel-Information) ![Staircase](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/f73d38df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/97469747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/3d878f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Farmington Inn & Suites Farmington 8.8/10 Excellent (1002) "Tip quality, charming place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nello CA $186 CA $239 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/53845527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/1a9de5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/5338d0fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/8a5f6b59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Southington, CT Southington 9.2/10 Wonderful (1007) "Great staff, clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $179 CA $205 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Southington.h6476838.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=2025-12-11&endDate=2025-12-12®ionId=183057&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_183057) ## Top Cheshire Hotel Reviews ![Hampton Inn & Suites Hartford/East Hartford](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "Fun staff" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![Avon Old Farms Hotel](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "Beautiful room and property. Had a wonderful time! Definitely will stay again. " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "I didn't know about breakfast" [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "The rooms are nice and the staff is accommodating. The fitness center could use an upgrade " [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Brookside Park](https://www.expedia.ca/Brookside-Park-Hotels.0-l553248621557919974-0.Travel-Guide-Filter-Hotels) - [B&B in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Country Houses in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Country-House.d6346724-aaCountryHouse.Travel-Guide-Accommodation) - [Guest Houses in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Guest-Houses.d6346724-aaGuestHouses.Travel-Guide-Accommodation) - [Villas in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Villas.d6346724-aaVillas.Travel-Guide-Accommodation) - 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