Title: Book the Best Canaan LUXURY Hotels - Upscale Hotels in Canaan, NY | Expedia.ca [Hotels in Canaan](https://expedia.ca/Canaan-Hotels.d55619.Travel-Guide-Hotels)[Vacation Rentals in Canaan](https://expedia.ca/Canaan-Vacation-Rentals.d55619.Travel-Guide-VacationRentals)[Flights to Canaan](https://expedia.ca/Cheap-Flights-To-Canaan.d55619.Travel-Guide-Flights)[Canaan Car Rentals](https://expedia.ca/Car-Rentals-In-Canaan.d55619.Car-Rental-Guide)[Canaan Vacation Packages](https://expedia.ca/Canaan.d55619.Destination-Travel-Guides) ![Yum](https://images.trvl-media.com/place/55619/197bfc88-eb1a-46ea-aa51-dc0f5f649d4e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Robin/Loving Life ![](https://images.trvl-media.com/place/55619/197bfc88-eb1a-46ea-aa51-dc0f5f649d4e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Luxury Hotels Tonight [Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-01-24&endDate=2026-01-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-01-25&endDate=2026-01-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Canaan luxury hotels ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (290 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $197 CA $231 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/a093eeea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (354 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $130 CA $145 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #10 Queen's Cottage | Living room](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/4f8b66e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (134 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $424 CA $513 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/8a8cd518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/755fb8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Thayer House, Room 201, 1 King bed, Jetted tub](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/f1d5c4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/6afab6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Inn On The Green [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) Great Barrington 9.2/10 Wonderful (90 reviews) "Beautiful Inn and outstanding chef" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $418 CA $504 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $565 CA $631 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.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=2026-02-07&endDate=2026-02-08®ionId=55619&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Canaan Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Great property, very accommodating. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Room is great for families. Bit dated but clean and spacious." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "generally good" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "It can be hard trying to choose a place to stay lately, especially since AI has blown up. I'm so happy I gave this place a chance. The staff was extremely friendly and helpful. Not once did I feel like they didn't want to be there. When we checked out at noon (which is an amazing checkout time), they held our luggage and bags for us. When we came back many hours later they offered to let us use the restroom before going to the train station. Most places in NYC don't want anything to do with you once you're checked out. The rooms were clean, and everything worked, including the wifi and heat/ac. I would definitely take my family back to stay here on another NYC trip. The room price was also very reasonable for the city. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Very clean...i dotted and t crossed" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Great place to stay if you enjoy paying less money and still sleeping well. Inexpensive, clean, quiet, and ridiculously convenient—just a short two-block stroll to the downtown strip for shopping and restaurants (close enough to walk, far enough to avoid the noise). Only 2.5 miles down a local road to Butternut ski mountain, so you’ll be on the slopes before your coffee fully kicks in. CVS shares the same parking lot, which is perfect in case you forget toothpaste, sunscreen, or your dignity. Most importantly—and let’s be honest, this matters—a beer, wine, liquor, and cheese shop is only one mile down the road. Priorities are clearly respected here. Rooms are clean, beds are super comfortable, and the décor politely reminds you that time exists. Free breakfast is solid but not life-changing: eggs, toast, sausage, waffles, yogurt, coffee, fruit—everything you need to function, nothing you’ll write poetry about. Bathroom fans are loud, but they drown out the 1 time per day freight train in the back yard, so net positive. Overall, a great stay, and for the cheap nightly price, it’s basically unbeatable unless you’re expecting chandeliers and a personal butler. Enjoy! " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ## Frequently asked questions ### Which area of Canaan is best to stay in for luxury hotels? > This region is characterised by its scenic countryside, rolling hills, and a more spread-out, private feel compared to denser urban areas. While not a traditional "neighbourhood" with a central square, luxury hotels here tend to be set back from the main road, offering expansive grounds and a focus on tranquility. You'll find these properties often boast amenities like fine dining restaurants, extensive spa facilities, and well-maintained outdoor spaces. > > > Couples looking for a private and serene escape will find this area particularly appealing. The luxury hotels here often cater to a desire for relaxation and high-end service, with opportunities for quiet walks, spa treatments, and gourmet meals without needing to leave the property. ### How much does a luxury hotel in Canaan cost? ### What luxury activities and experiences are there in Canaan? > This region is known for its expansive private estates and high-end retreats, often featuring stunning views of the Berkshire Mountains. You'll find properties designed for comfort and privacy, with amenities like personal chefs, private pools, and bespoke concierge services. Many of these are located in secluded spots, providing a tranquil environment. > > > Couples looking for a romantic and exclusive getaway will find this area particularly appealing. They can enjoy private dining experiences, spa treatments within their accommodation, or explore the quiet country roads. The focus here is on personalised service and tailored experiences, from organised hikes to private wine tastings. ### How can I save on a luxury hotel in Canaan with Expedia? ### Is it cheaper to book a luxury Canaan hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Albany ](https://www.expedia.ca/Albany-Hotels-Hotels-With-Bar.0-0-d603260-tHotelswithBar.Travel-Guide-Filter-Hotels) - 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