Title: Book the Best Hotels with POOL in Pittsfield in 2026 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d146411.Destination-Travel-Guides) ![Court House in Pittsfield](https://images.trvl-media.com/place/146411/e1162892-98db-4e1f-aa10-c1e92fa5be83.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/146411/e1162892-98db-4e1f-aa10-c1e92fa5be83.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 Pittsfield Hotels with a Pool Tonight [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2026-01-15&endDate=2026-01-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Pittsfield ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/6afc32c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (King Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/80a90a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/23a03799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/b7c49e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### William Watson Hotel [](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) Pittsfield 9.2/10 Wonderful (348 reviews) "Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Druann CA $116 CA $128 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/87b66cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/6dfa4459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a47c0b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Accessible](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/6d442adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Acres Hotel [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) Pittsfield 8.6/10 Excellent (141 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeramy CA $149 CA $163 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/946d8e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/1af516fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/873e4e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/b4ce7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monroe Street Suites [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) Pittsfield 9.6/10 Exceptional (58 reviews) "We had a great stay and would recommend others to stay here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brady CA $136 CA $149 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/0aa674c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e9aab2d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/62575d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/74c9995c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) Pittsfield 6.8/10 (127 reviews) "Our stay was pleasant and quiet, the only problem was that the heat was not sufficient to keep the room warm during extreme cold wave. Other than that it was fairly clean, and the staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tod CA $82 CA $91 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/304bbf41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-bfee123b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-36d6779a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1080h1437x0y3-5f7123c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.Hotel-Information) Pittsfield CA $348 CA $488 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/8b37aa59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/ab409a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/70ba5f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/a4991647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake. [](https://www.expedia.ca/Pittsfield-Hotels-Lovers-Lakeside-Love-Nest-Cozy-Retreat-On-Pittsfields-Serene-Lake.h109522338.Hotel-Information) Pittsfield CA $372 CA $512 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Pittsfield-Hotels-Lovers-Lakeside-Love-Nest-Cozy-Retreat-On-Pittsfields-Serene-Lake.h109522338.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/2cb4a716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/5cf5de0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/e95aba72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/164bb1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River's Edge Motel [](https://www.expedia.ca/Hannibal-Hotels-Rivers-Edge-Motel.h12232142.Hotel-Information) Louisiana 9.0/10 Wonderful (358 reviews) "Excellent stay !!! Quite " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradley CA $111 CA $126 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Hannibal-Hotels-Rivers-Edge-Motel.h12232142.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/9536012a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/50983b3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/2c8ee78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Single Room](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/16cb28cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Eagles Nest Inn [](https://www.expedia.ca/Louisiana-Hotels-The-Eagles-Nest-Inn.h111944656.Hotel-Information) Louisiana 9.4/10 Exceptional (19 reviews) "It was very clean and very nice place to stay, has a very home and cozy feeling walking into the room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $133 CA $151 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Louisiana-Hotels-The-Eagles-Nest-Inn.h111944656.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/22ecf069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/8a5e60e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/08fef4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/b068773a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy room located in historic downtown with a 5 minute walk to the riverfront! [](https://www.expedia.ca/Louisiana-Hotels-Cozy-Room-Located-In-Historic-Downtown-With-A-5-Minute-Walk-To-The-Riverfront.h96126590.Hotel-Information) Louisiana 10/10 Exceptional (1 review) "Great property. Highly recommend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan A. CA $156 CA $194 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Louisiana-Hotels-Cozy-Room-Located-In-Historic-Downtown-With-A-5-Minute-Walk-To-The-Riverfront.h96126590.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w906h683x60y0-f10f078b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w547h683x240y0-d6fb1b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-bbfcfe44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-6bba3640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) Jacksonville 10/10 Exceptional (15 reviews) "Always a nice place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pete D. CA $137 CA $175 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.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=2026-01-28&endDate=2026-01-29®ionId=146411&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ## Frequently asked questions ### What are some hotels with pools in Pittsfield? ### What is there to see and do in Pittsfield? ### When is the best time to book a hotel with a pool in Pittsfield? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Barry ](https://www.expedia.ca/3Star-Barry-Hotels.s30-0-d3000433380.Travel-Guide-Filter-Hotels) - [Alsey Hotels ](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [B&B in Atlas ](https://www.expedia.ca/Atlas-Bed-And-Breakfast.d3000346106-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Atlas ](https://www.expedia.ca/Atlas-Cabins.d3000346106-aaCabins.Travel-Guide-Accommodation) - [Hotels with a Pool in Atlas ](https://www.expedia.ca/Atlas-Hotels-Hotel-With-Pool.0-0-d3000346106-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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