Title: Book the Best Canaan FAMILY FRIENDLY Hotels from CA $117 - Kid-Friendly 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) ![](https://mediaim.expedia.com/destination/2/0367124872be85648d8997189b889b71.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Robin/Loving Life # Find Family Hotels in Canaan, NY from CA $117 ![](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 Family Hotels Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Canaan Family Hotels ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1018) "Good breakfast; pleasant staff on duty 24/7; convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan and Alice CA $142 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (916) "Enjoyable stay. Staff were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire CA $144 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.2/10 Wonderful (1002) "Great Indian restaurant in the hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $149 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/f1aeba62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.4/10 Exceptional (6) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $189 CA $211 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/fd39ba7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.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) ### Travelodge by Wyndham Great Barrington Berkshires Great Barrington 7.6/10 Good (554) "Excellent location, friendly service, clean, comfortable room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $105 CA $117 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Egyptian cotton sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/be4af91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/a2e409f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prospect Berkshires Egremont 9.4/10 Exceptional (11) "Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $357 CA $446 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![Skiing](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/107313fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort Hancock 8.2/10 Very good (983) "This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $196 CA $219 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/71ad964e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/w1127h1499x0y0-42ebd11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/d3489cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/375e2d43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Cat Lodge Copake Falls 9.4/10 Exceptional (61) "This is a very cute lodge, updated with a bit of vintage charm. Close to all the Berkshires must sees and nature hiking trails. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kayla CA $213 CA $238 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hillsdale-Hotels-Little-Cat-Lodge.h94739508.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/7e059c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, Ensuite (Early American Suite 201)](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/366b65ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/d7cd7f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ba469908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1896 House Country Inn & Motels Williamstown 6.6/10 (448) "The price is good. It's a classic motel from the '50's, but gets the job done." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) edson CA $132 CA $148 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/f2aaf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.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) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires Great Barrington 9.4/10 Exceptional (745) "The property is very nice and the staff was extremely friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $200 CA $223 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.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=2025-11-06&endDate=2025-11-07®ionId=55619&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Canaan Hotel Reviews ![Fairfield Inn & Suites Albany East Greenbush](//images.trvl-media.com/lodging/1000000/700000/694500/694459/a8f36cd0_y.jpg) ### Fairfield Inn & Suites Albany East Greenbush 10/10 Excellent "Everything here was first rate including the service and the room." [](https://expedia.ca/Albany-Hotels-Fairfield-Inn-Suites-Albany-East-Greenbush.h694459.Hotel-Information) ![Hampton Inn & Suites Albany-East Greenbush](//images.trvl-media.com/lodging/16000000/15730000/15725300/15725242/24123a32_y.jpg) ### Hampton Inn & Suites Albany-East Greenbush 10/10 Excellent "Overall experience was exceptional. " [](https://expedia.ca/Albany-Hotels-Hampton-Inn-Suites-Albany-East-Greenbush.h15725242.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "In a very nice annex suite." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Comfort Inn & Suites East Greenbush - Albany](//images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "Quiet" [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Enjoyable stay. Staff were very nice. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try to come down twice a month from CNY--needless to say it is expensive for me.. Random question-- do you offer discounts?" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Clean room, nice view" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Breakfast was great" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Frequently asked questions ### What's Canaan like for family-friendly vacations? > If you've been thinking about a trip with your kids, the budget-friendly destination of Canaan is a good choice. The museums, local tours, and coffee shops are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 15.8 mi (25.4 km) from the city center. ### When's the best time to book a family-friendly vacation in Canaan? > The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What's there to see and do with your family in Canaan? > While you are visiting Canaan, you might want to round up the kiddos and make time to see interesting attractions such as Tanglewood Music Center and Bousquet Ski Area. Make sure you have lots of time for activities like Shakespeare and Company and Ventfort Hall Mansion and Gilded Age Museum. ## 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) - [Hotels with Tennis Courts in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Tennis-Courts.0-0-d603260-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - 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