Title: Book the Best Canaan WINERY Hotels in 2025 | Expedia.ca [Hotels in Canaan](https://expedia.ca/Canaan-Hotels.d6003925.Travel-Guide-Hotels)[Vacation Rentals in Canaan](https://expedia.ca/Canaan-Vacation-Rentals.d6003925.Travel-Guide-VacationRentals)[Canaan Car Rentals](https://expedia.ca/Car-Rentals-In-Canaan.d6003925.Car-Rental-Guide)[Canaan Vacation Packages](https://expedia.ca/Canaan.d6003925.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/winery.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Canaan, CT from CA $207 - ![](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 Canaan Winery Hotels Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6003925&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6003925&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6003925&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6003925&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Canaan Winery Hotels ![Premium Apartment | Private kitchen](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn Great Barrington 9.4/10 Exceptional (35) "Quiet and peaceful location set off the road, with woodsy area in the back. Very close to Main Street shops and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $185 CA $207 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/074ac974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/56c0072d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/4e24f0c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/1e2f9086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### the suite @ barn & bike - private, bucolic, serene setting Red Hook 9.8/10 Exceptional (14) "We enjoyed our stay at this quiet, cozy property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $231 CA $354 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Red-Hook-Hotels-The-Suite-Gallatin-Farmstead-Private.h76400133.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/3333094f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/4ae56ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/757359f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101460000/101453000/101452935/30f9da27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming apartment 7 minute walk to downtown Torrington 10/10 Exceptional (15) "We had an amazing stay. The property was very clean and welcoming. Personal touches made us feel at home. A great location close to walking path and downtown. Would highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer b. CA $188 CA $348 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Torrington-Hotels-Charming-Apartment-Minutes-From-Downtown.h101452935.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/77e07421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake! Sherwood Forest 10/10 Exceptional (3) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. CA $204 CA $528 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/21b3ce2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/eb2f9471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/a012462e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/6f907e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### rural, serene + sophisticated space Red Hook 10/10 Exceptional (7) "A beautifully curated barn overlooking a picturesque landscape. Gregg, the owner, really cares and wants to make sure you have everything you need. We stayed over a weekend when we were attending a wedding in the area. It was so nice to have a place to relax amidst all the festivities. The birdsong and bullfrog chorus led us to some of the soundest sleep we’ve enjoyed in a long time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $307 CA $483 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Red-Hook-Hotels-Rural.h36245067.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/9eeeead4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/0cd1f311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. Great Barrington CA $476 CA $823 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.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=2025-11-15&endDate=2025-11-16®ionId=6003925&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Canaan Hotel Reviews ![Days Inn by Wyndham Torrington](//images.trvl-media.com/lodging/1000000/50000/50000/49932/dd052437_y.jpg) ### Days Inn by Wyndham Torrington 10/10 Excellent "Very simple, clean comfortable room" [](https://expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "It was really nice staying here. The room was clean, bed was comfortable, and there was a mini-fridge that wasn't full of expensive drinks you're not supposed to touch! It was mostly quiet, except for the trains at night that pass behind the building. It is very close by to shops, cool architecture, and a nice walking path. Very safe area too. The breakfast wasn't the best, but it's free, and you can easily pop in to nearby restaurants if you want something better. The staff are very friendly and helpful. I would recommend staying here! It's a nice place to stay for the price." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg) ### Monument Mountain Motel 10/10 Excellent "5 stars!" [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Travelodge by Wyndham Great Barrington Berkshires](//images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51_y.jpg) ### Travelodge by Wyndham Great Barrington Berkshires 10/10 Excellent "The staff were very friendly and accommodating " [](https://expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](//images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires 10/10 Excellent "Anthony , the Front Desk person who checked us in , is great - Marriott is lucky to have him!" [](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Americas Best Value Inn Torrington CT](//images.trvl-media.com/lodging/1000000/10000/5800/5738/a9b48332_y.jpg) ### Americas Best Value Inn Torrington CT 10/10 Excellent "Excellent parking." [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ![The Litchfield Inn](//images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/9aa3fa98_y.jpg) ### The Litchfield Inn 10/10 Excellent "Upscale. Clean and quiet. 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