Title: Book the Best Cheshire Ski Hotels in 2025 from CA $124 | 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) ![](https://mediaim.expedia.com/destination/2/ab039a4411a79c16e7c533ffaba43069.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tai Bui # Find Ski Hotels in Cheshire, CT from CA $124 ![](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 [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-24&endDate=2025-10-26&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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/db5c54a9.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) ![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) ### Courtyard by Marriott Waterbury Downtown Waterbury 8.4/10 Very good (1018) "Wonderful stay " CA $125 CA $143 total includes taxes & fees Oct 19 - Oct 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) ![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) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/cb3d49ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG Southington 8.8/10 Excellent (1119) "Rooms are clean, staff was very pleasant, breakfast was great" CA $132 CA $151 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/44e097e7.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) ![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) ### Holiday Inn Cheshire - Southington by IHG Southington 8.2/10 Very good (1006) "The rooms were clean and staff were very attentive." CA $126 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f224bafd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/3fa625b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection Southbury 8.4/10 Very good (1002) "Great stay!!" CA $160 CA $203 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/814e9800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/fd0bf8f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/fea8ec49.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/c4681fb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Southington Southington 7.2/10 Good (1004) "The person who checked us in and out were very pleasant and polite. The breakfast was good. Rooms were big and water pressure on the shower was great. " CA $125 CA $143 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Southington.h49987.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/b4adea40.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 8.0/10 Very good (1005) "Very surprised how 10/10 this hotel is. " CA $131 CA $151 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-Milford.h13007.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) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d9f37f65.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) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/20124035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Avon Old Farms Hotel Avon 8.4/10 Very good (1008) "Breakfast was really good. They have great espresso machines " CA $195 CA $254 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.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 lounge](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/35c8e72d.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) ![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) "Enjoyed our stay!" CA $188 CA $241 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.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) ![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) ![Staircase](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/ec875b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Middletown Middletown 9.0/10 Wonderful (511) "Very nice property convenient to Wesleyan and Middletown" [](https://www.expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/14000/13976/83c84a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Cromwell - Middletown Cromwell 6.6/10 (1003) "I stay here whenever I'm in the Middletown area; convenient to where I need to get to. Good room; good price for what I want in a room" CA $108 CA $124 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Hartford-Hotels-Quality-Inn-Cromwell-Middletown.h13976.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=2025-10-26&endDate=2025-10-27®ionId=183057&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![Holiday Inn Express Southington by IHG](//images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Fine" [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Clean good description as given in app" [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](//images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "Very comfortable, decent facilities and great staff - would recommend!" [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Red Roof Inn Meriden](//images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg) ### Red Roof Inn Meriden 10/10 Excellent "The staff was nice and the facilities were clean" [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.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) - 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