Title: Book the Best Hotels with POOL in Old Chatham in 2026 | Expedia.ca [Hotels in Old Chatham](https://expedia.ca/Old-Chatham-Hotels.d6190671.Travel-Guide-Hotels)[Vacation Rentals in Old Chatham](https://expedia.ca/Old-Chatham-Vacation-Rentals.d6190671.Travel-Guide-VacationRentals)[Flights to Old Chatham](https://expedia.ca/Cheap-Flights-To-Old-Chatham.d6190671.Travel-Guide-Flights)[Old Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Chatham.d6190671.Car-Rental-Guide)[Old Chatham Vacation Packages](https://expedia.ca/Old-Chatham.d6190671.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 Old Chatham Hotels with a Pool Tonight [Mar 1 - Mar 2](https://www.expedia.ca/Hotel-Search?regionId=6190671&startDate=2026-03-01&endDate=2026-03-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 2 - Mar 3](https://www.expedia.ca/Hotel-Search?regionId=6190671&startDate=2026-03-02&endDate=2026-03-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6190671&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6190671&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Old Chatham hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b548733b.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) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.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 (21 reviews) - Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood. CA $190 CA $212 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,002 reviews) - Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming. CA $126 CA $141 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) Pittsfield 9.0/10 Wonderful (866 reviews) - Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences. CA $155 CA $204 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### 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 (742 reviews) - Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment. CA $146 CA $163 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (554 reviews) - Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires. CA $150 CA $168 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (834 reviews) - Summertime splashes await at this refreshing outdoor pool oasis in Lenox. CA $94 CA $105 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/45b65286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 3 Bedrooms, Mountainside | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/2f0dc604_edited_9c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/9722ad97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/8c32bd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) New Ashford 9.4/10 Exceptional (93 reviews) - Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits. CA $175 CA $192 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/739b3363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/27b1a758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/70501210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/9ec4188c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone [](https://www.expedia.ca/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information) Hancock 10/10 Exceptional (11 reviews) - Experience year-round aquatic bliss with indoor pool and hot tub at this ski-in/ski-out apartment with mountain views. CA $147 CA $326 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/f74a2d8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/ced4a56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1333h900x16y0-bf275b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated [](https://www.expedia.ca/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information) Hancock 10/10 Exceptional (5 reviews) - Jiminy Peak apartment offers ski-in/ski-out access, heated indoor pool, and private soaks after mountain adventures. CA $143 CA $320 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/857eb070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/e6beff93_edited_6ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/w1008h683x16y0-86131c43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73070000/73062200/73062141/2d6ee5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn [](https://www.expedia.ca/Hancock-Hotels-Deluxe-Yeti-Suite-On-Jiminy-Mtn-1st-Flr-Sleeps-4-New-Fully-Redone-Country-Inn.h73062141.Hotel-Information) Hancock 9.8/10 Exceptional (22 reviews) CA $143 CA $320 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Hancock-Hotels-Deluxe-Yeti-Suite-On-Jiminy-Mtn-1st-Flr-Sleeps-4-New-Fully-Redone-Country-Inn.h73062141.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=2026-03-16&endDate=2026-03-17®ionId=6190671&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Old Chatham Breakfast included 4 stars 5 stars Hot tub Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_6190671) ## Top Old Chatham Hotel Reviews ![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 "The rooms were spacious, the staff are super friendly. This is our second time staying and we will continue to book in the future. The pool and hot tub was nice. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Clean room, breakfast was good👍" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hilton Albany](https://images.trvl-media.com/lodging/1000000/430000/424500/424407/b38d0fca_y.jpg) ### Hilton Albany 10/10 Excellent "Everything was great and location & especially the fitness center ❤️ it" [](https://expedia.ca/Albany-Hotels-Hilton-Albany.h424407.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 "Friendly, clean place. Staff & guests always seem happy and polite. " [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean, breakfast was a nice option before heading to Butternut mountain nearby " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Hampton Inn & Suites Albany-Downtown](https://images.trvl-media.com/lodging/2000000/1290000/1287500/1287492/a974d7ec_y.jpg) ### Hampton Inn & Suites Albany-Downtown 10/10 Excellent "Big rioms" [](https://expedia.ca/Albany-Hotels-Hampton-Inn-Suites-Albany-Downtown.h1287492.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 customer service" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hilton Garden Inn Albany Medical Center](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644615/86b2c1e4_y.jpg) ### Hilton Garden Inn Albany Medical Center 10/10 Excellent "The room was spotless and the bed was comfortable. The microwave and fridge were a plus! The check-in was efficient and the staff member was knowledgeable and friendly. " [](https://expedia.ca/Albany-Hotels-Hilton-Garden-Inn-Albany-Medical-Center.h1644615.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 "Bathroom had somebody’s hair on the door and shower " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Old Chatham? ### What is there to see and do in Old Chatham? ### When is the best time to book a hotel with a pool in Old Chatham? ## 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) - 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