Title: Book the Best Chatham FAMILY FRIENDLY Hotels from CA $114 - Kid-Friendly Hotels in Chatham, NY | Expedia.ca [Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d6046736.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d6046736.Destination-Travel-Guides) ![Tracy Memorial Village Hall, Chatham, New York](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.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 Chatham Family Hotels Tonight [Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-02&endDate=2026-02-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Chatham family-friendly hotels ![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) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/1000000/790000/790000/789964/5740b713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) Pittsfield 8.6/10 Excellent (1,000 reviews) "Very friendly and good Breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse CA $127 CA $142 total includes taxes & fees Feb 6 - Feb 7 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.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/e88abd9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1,002 reviews) "Staff was very courteous and rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $133 CA $149 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1,001 reviews) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan CA $133 CA $149 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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, 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) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.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 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (567 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad CA $102 CA $114 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/f6e88d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/f6bbe693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/fa243b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites East Greenbush - Albany [](https://www.expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) Castleton-on-Hudson 8.6/10 Excellent (1,001 reviews) "I have stayed here many times and have had good experiences always." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $134 CA $148 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.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) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (18 reviews) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $189 CA $211 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/210000/201300/201283/25cd266c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/210000/201300/201283/8503ac1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/210000/201300/201283/451dfab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Kitchenette | Living area](https://images.trvl-media.com/lodging/1000000/210000/201300/201283/e49295d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton West Coxsackie [](https://www.expedia.ca/West-Coxsackie-Hotels-Spark-By-Hilton-West-Coxsackie.h201283.Hotel-Information) West Coxsackie 7.8/10 Good (90 reviews) "clean place - would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andradys CA $122 CA $131 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/West-Coxsackie-Hotels-Spark-By-Hilton-West-Coxsackie.h201283.Hotel-Information) ![Arcade](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/28c3ccfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) South Lee 9.0/10 Wonderful (829 reviews) "Great overnights stay, wish I was here longer " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $153 CA $198 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/11900/11858/8d1e9400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11900/11858/2adb37bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/11900/11858/a132ab2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11900/11858/3125aefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Glenmont - Albany South [](https://www.expedia.ca/Albany-Hotels-Comfort-Inn-Glenmont-Albany-South.h11858.Hotel-Information) Glenmont 7.8/10 Good (1,001 reviews) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolann CA $123 CA $141 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Albany-Hotels-Comfort-Inn-Glenmont-Albany-South.h11858.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.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) ![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 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) Great Barrington 9.4/10 Exceptional (765 reviews) "Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dinh CA $206 CA $230 total includes taxes & fees Feb 8 - Feb 9 [](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=2026-02-16&endDate=2026-02-17®ionId=6046736&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at family-friendly hotels in Chatham 4 stars 5 stars Restaurant Water park Pool ## Top Chatham 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 clean room. Staff great. Breakfast and selection great! " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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 "Immaculately clean and friendly staff. Easy parking and great breakfast" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "Quiet, clean," [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Great staff, beautiful hotel. Would definitely recommend " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "Everything was great, the staff, the room, and the amenities. We will be coming back. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Fairfield Inn & Suites Albany East Greenbush](https://images.trvl-media.com/lodging/1000000/700000/694500/694459/a8f36cd0_y.jpg) ### Fairfield Inn & Suites Albany East Greenbush 10/10 Excellent "Great . Clean and Friendly Staff" [](https://expedia.ca/Albany-Hotels-Fairfield-Inn-Suites-Albany-East-Greenbush.h694459.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 "Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. " [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Frequently asked questions ### What's Chatham like for family-friendly vacations? ### When's the best time to book a family-friendly vacation in Chatham? ### What's there to see and do with your family in Chatham? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - 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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