Title: 2 Stars Hotels in Winsted, Connecticut from CA $115 - Find Cheap Winsted Hotels With 2 Stars | Expedia.ca [Winsted Travel Guide](https://expedia.ca/Winsted.dx3000430645)[Hotels in Winsted](https://expedia.ca/Winsted-Hotels.d3000430645.Travel-Guide-Hotels)[Vacation Rentals in Winsted](https://expedia.ca/Winsted-Vacation-Rentals.d3000430645.Travel-Guide-VacationRentals)[Flights to Winsted](https://expedia.ca/Cheap-Flights-To-Winsted.d3000430645.Travel-Guide-Flights)[Winsted Car Rentals](https://expedia.ca/Car-Rentals-In-Winsted.d3000430645.Car-Rental-Guide)[Winsted Vacation Packages](https://expedia.ca/Winsted.d3000430645.Destination-Travel-Guides) ![A tractor up a tree! And, there's a picnic table underneath.](https://images.trvl-media.com/place/6125522/bf8d15d8-5a06-4bf9-b059-b9dc4d18a280.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Kim Knox Beckius # 2 Stars Hotels in Winsted, Connecticut from CA $115 - ![](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 Winsted 2 Star Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-12&endDate=2025-12-13&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-13&endDate=2025-12-14&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000430645&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winsted 2-star hotels ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/df2a9cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/1fe78714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/273b965f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/bab32d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Suites Hartford Farmington [](https://www.expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) Farmington 8.0/10 Very good (1003) "Clean room with a good bed, good shower and an excellent TV " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lester CA $105 CA $121 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/c57c2497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/5f21961b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/9360dc5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535956/8da3ecb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Bradley Airport by IHG [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Suites-Bradley-Airport.h1535956.Hotel-Information) Windsor Locks 9.0/10 Wonderful (1155) "Good place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $157 CA $181 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Suites-Bradley-Airport.h1535956.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/f9413aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/21d5040e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/2f812c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/ee4e9e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Hartford/Farmington [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) Farmington 8.8/10 Excellent (1000) "Clean room and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $149 CA $171 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/396dc82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/b9e04d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/0c1a7e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/b0f2cd95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Hartford/Airport [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-HartfordAirport.h892590.Hotel-Information) Windsor 9.0/10 Wonderful (1002) "Rooms were clean and beds were super comfy. Free shuttle was a huge bonus as well. Definitely recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RANDA CA $136 CA $156 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-HartfordAirport.h892590.Hotel-Information) ![Desk, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/c8b8e6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/bfea9bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/d4c8ac0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/4463ebe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Torrington [](https://www.expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) Torrington 7.4/10 Good (1000) "Clean comfortable room,great parking and local shopping " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $116 CA $133 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/dcdd836c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) Great Barrington 8.8/10 Excellent (707) "We stay here every year and it never disappoints " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $147 CA $165 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/51285776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/afa8b6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/d8217024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/5f79da29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Westfield - Springfield [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information) Westfield 7.2/10 Good (903) "Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gloria CA $128 CA $143 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information) ![Premium bedding, down comforters, Select Comfort beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5800/5738/3b028198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5800/5738/19fb4ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/5800/5738/71bf9e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5800/5738/56fa1d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Americas Best Value Inn Torrington CT [](https://www.expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) Torrington 5.6/10 (779) "Walls are thin but it was clean and safe with friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $141 CA $162 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/591bd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) Great Barrington 8.4/10 Very good (1002) "Clean room, nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devron CA $104 CA $117 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/ac051f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/9c0a3e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/8f354477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/w531h370x4y0-37170d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Plainville [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) Plainville 8.6/10 Excellent (908) "Great place stayed several times." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marlene D CA $120 CA $138 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/34065f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/cd83e31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Refrigerator](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/04ad8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/241daa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Westfield [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information) Westfield 8.4/10 Very good (816) "Very pet friendly and the night check in agent was super kind and friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) olivia townsend CA $143 CA $160 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) Great Barrington 9.0/10 Wonderful (804) "Yes it was clean & staff was very polite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara L. [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.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/1000000/920000/913200/913175/c93f6ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1c5bd04f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) Great Barrington 9.4/10 Exceptional (758) "Clean room, very courteous staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $186 CA $208 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (562) "The staff were very friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $103 CA $115 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/78000000/77190000/77186600/77186537/04fbcde1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/78000000/77190000/77186600/77186537/259c0b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/78000000/77190000/77186600/77186537/1d7ebb3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/78000000/77190000/77186600/77186537/93b7c17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PLYMOUTH MOTOR LODGE [](https://www.expedia.ca/Terryville-Hotels-PLYMOUTH-MOTOR-LODGE.h77186537.Hotel-Information) Terryville 7.6/10 Good (178) "Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $104 CA $120 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Terryville-Hotels-PLYMOUTH-MOTOR-LODGE.h77186537.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/143186d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Wilder House Berkshires Room 1](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/aa99cb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/0603c149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilder House Berkshires [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) Sheffield 9.8/10 Exceptional (38) "Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison CA $214 CA $240 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95650000/95648100/95648076/7eadfce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95650000/95648100/95648076/80433a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95650000/95648100/95648076/e7a73d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/96000000/95650000/95648100/95648076/5660536c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hitching Post Country Motel [](https://www.expedia.ca/Cornwall-Bridge-Hotels-45-Kent-Rd-S.h95648076.Hotel-Information) Cornwall Bridge 6.6/10 (80) "Basic accommodation that was clean and easy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $179 CA $206 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Cornwall-Bridge-Hotels-45-Kent-Rd-S.h95648076.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/51ca9ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room, 2 Queen Beds, Courtyard View](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) Great Barrington 9.4/10 Exceptional (36) "We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $183 CA $205 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/ecdcd2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/5fe2b5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (5)](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/6375a3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (5) | Bathroom](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/3ff31723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Millerton Inn [](https://www.expedia.ca/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) Millerton 8.0/10 Very good (9) "Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $222 CA $251 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce4ac8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/92ecbd6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce870576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/8311b1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Family Retreat | Near Downtown Hartford | Sleeps 10 [](https://www.expedia.ca/Bloomfield-Hotels-Modern-Family-Retreat-Near-Downtown-Hartford-Sleeps-10.h108190201.Hotel-Information) Bloomfield 9.4/10 Exceptional (3) "There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joslynn T. CA $397 CA $948 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Bloomfield-Hotels-Modern-Family-Retreat-Near-Downtown-Hartford-Sleeps-10.h108190201.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%2F2Star-Winsted-Hotels.s20-0-d3000430645.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Winsted-Hotels.s20-0-d3000430645.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Winsted. ![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sheraton Hartford Hotel at Bradley Airport 1 Bradley International Airport Windsor Locks CT CA $315 CA $363 total Jan 5 - Jan 6, 2026 includes taxes & fees 9/10 Wonderful! (1,006 reviews) [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Farmington Inn & Suites 827 Farmington Ave Farmington CT CA $126 CA $169 total Dec 29 - Dec 30 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Avon Old Farms Hotel](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Avon Old Farms Hotel 279 Avon Mountain Rd Avon CT CA $137 CA $187 total Dec 28 - Dec 29 includes taxes & fees 8.2/10 Very Good! (1,005 reviews) [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) Still don't see what you're looking for? [See all properties in Winsted.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=3000430645&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=3000430645&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=3000430645&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=3000430645&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=3000430645&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=3000430645&star=20&star=20&amenities=WATER_PARK) 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. ## Learn more about Winsted Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes. [See all hotels in Winsted](https://www.expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27&adults=2®ionId=3000430645) ![A tractor up a tree! And, there's a picnic table underneath.](https://images.trvl-media.com/place/6125522/bf8d15d8-5a06-4bf9-b059-b9dc4d18a280.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by Kim Knox Beckius ## Top Winsted Hotel Reviews ## Find out more about Winsted Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Winsted, Winsted you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in Winsted are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. 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