Title: Book the Best The Berkshires FAMILY FRIENDLY Hotels from CA $113 - Kid-Friendly Hotels in The Berkshires, MA | Expedia.ca [The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Vacation Rentals in The Berkshires](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) ![The Berkshires which includes flowers](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau ![](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.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 The Berkshires Family Hotels Tonight [Mar 19 - Mar 20](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-03-19&endDate=2026-03-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Mar 20 - Mar 21](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-03-20&endDate=2026-03-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for The Berkshires family-friendly hotels ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.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) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.2/10 Wonderful (1,000 reviews) - Family fun at lakeside retreat with kayaking, fishing, and premium TV channels. CA $128 CA $143 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.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 (855 reviews) CA $154 CA $199 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.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) ### 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 (773 reviews) - Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut. CA $208 CA $232 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.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) - Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails. CA $146 CA $164 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/0e8cd0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) Williamstown 9.6/10 Exceptional (598 reviews) CA $136 CA $151 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6ac710dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) Williamstown 9.2/10 Wonderful (896 reviews) CA $108 CA $128 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/b2a572bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (87 reviews) - Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre. CA $181 CA $202 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/7720f0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/823465a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) Williamstown 9.4/10 Exceptional (315 reviews) CA $101 CA $113 total includes taxes & fees Apr 9 - Apr 10 [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.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) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.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) ### Jiminy Peak Mountain Resort [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) Hancock 8.2/10 Very good (989 reviews) - Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak. CA $204 CA $228 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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 (573 reviews) - Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms. CA $103 CA $115 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.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=2026-04-02&endDate=2026-04-03®ionId=6047665&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at family-friendly hotels in The Berkshires Breakfast included Pool All-inclusive 4 stars 5 stars ## Family-friendly hotels with free breakfast in The Berkshires ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.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) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.2/10 Wonderful (1000) CA $128 CA $143 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.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) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.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 (855) CA $154 CA $199 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.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 (1000) CA $146 CA $164 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.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) ![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) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/c93f6ba5.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 (773) CA $208 CA $232 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/f3854c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) Williamstown 9.6/10 Exceptional (598) CA $136 CA $151 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/51c14a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/823465a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) Williamstown 9.4/10 Exceptional (315) CA $101 CA $113 total includes taxes & fees Apr 9 - Apr 10 [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/b2a572bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (87) CA $181 CA $202 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6df66696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) Williamstown 9.2/10 Wonderful (896) CA $108 CA $128 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.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) ### 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 (1000) CA $158 CA $177 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 (573) CA $103 CA $115 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03®ionId=6047665&adults=2&travelerType=family_friendly&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Family-friendly hotels with pools in The Berkshires ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.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) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.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 (855) CA $154 CA $199 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/f3854c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) Williamstown 9.6/10 Exceptional (598) CA $136 CA $151 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6df66696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) Williamstown 9.2/10 Wonderful (896) CA $108 CA $128 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/b2a572bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (87) CA $181 CA $202 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.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) ![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) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/c93f6ba5.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 (773) CA $208 CA $232 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.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) ### Jiminy Peak Mountain Resort [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) Hancock 8.2/10 Very good (989) CA $204 CA $228 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.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) ### 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 (1000) CA $158 CA $177 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/d08b3a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/7ca07411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/98afb96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/ecc89925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 [](https://www.expedia.ca/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information) Hancock 9.8/10 Exceptional (7) CA $157 CA $339 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information) ![Gift shop](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/2b285fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/e60e5176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/d4a1d841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/78a1069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor [](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information) Hancock 10/10 Exceptional (3) CA $156 CA $338 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/cb4793bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/w1008h683x16y0-213f51bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/d4f0c0c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con [](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information) Hancock 9.8/10 Exceptional (74) CA $362 CA $757 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.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=2026-04-02&endDate=2026-04-03®ionId=6047665&adults=2&travelerType=family_friendly&sort=RECOMMENDED&amenities=POOL&openPlayBack=true) ## Find out more about The Berkshires ### Family friendly things to do in The Berkshires The Berkshires, a picturesque region in Western Massachusetts, offers a plethora of family-friendly activities that promise a delightful getaway. Begin with a visit to the Berkshire Museum in Pittsfield, where kids can explore interactive exhibits, including a live aquarium and art galleries that spark creativity. For outdoor enthusiasts, the thrill of hiking at Mount Greylock State Reservation presents breathtaking views and trails suitable for all ages, making it an exciting adventure for the whole family. Art lovers will appreciate the renowned Norman Rockwell Museum in Stockbridge, where children can engage with America's favourite illustrator's work through family-friendly programs and tours. Another must-see is the Tanglewood Music Center, where families can enjoy picnics on the lawn while listening to the Boston Symphony Orchestra during the summer concerts. Finally, a trip to the Hancock Shaker Village offers a unique glimpse into historical living, with hands-on activities that educate and entertain. For accommodation, consider staying in Lenox, which boasts charming family-friendly hotels that often feature spacious rooms and amenities like pools and on-site dining. This central location allows easy access to these attractions, ensuring you can spend more time making memories and less time on the road. ## Top The Berkshires Hotel Reviews ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 10/10 Excellent "Clean, quiet, and a great breakfast! The staff was friendly. We enjoyed a fire in our room and the free bottle of wine. " [](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg) ### Hotel On North 10/10 Excellent "The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "yes" [](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 "Easy check-in; accommodating staff; clean room. Convenient but also quiet location." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034_y.jpg) ### Courtyard by Marriott Lenox Berkshires 10/10 Excellent "Clean room, friendly and helpful staff. " [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg) ### Quality Inn Great Barrington 10/10 Excellent "Clean room, recently renovated" [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "In the process of remodeling, but my room which was already renovated was very nice, as was the breakfast room. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 6/10 Okay "My room smelt like mold. The hotel was very clean staff were very nice. The beds were not comfortable . " [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/d239029a_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 8/10 Good "For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options." 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