Title: Book the Best Hotels with POOL in Pittsfield in 2025 | 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) # Find Hotels with a Pool in Pittsfield, IL from CA $88 - ![](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 [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-11-23&endDate=2025-11-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-11-24&endDate=2025-11-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Hotels with a Pool No exact matches found, but these alternatives could be just right ## Recommended hotels in Pittsfield ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/c466d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (New building)](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/2c579c3b.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) ### Green Acres Hotel Pittsfield 8.6/10 Excellent (141) "Wonderful stay - was staying with a number of family members and it all worked out" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $168 CA $185 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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) ![Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/13f55165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/16c3be32.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 6.8/10 (122) "Great little hotel, perfect for an overnight pit stop " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $80 CA $88 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/e9628a93.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) ![Double Room, Ensuite (Double Queen Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8f50dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### William Watson Hotel Pittsfield 9.2/10 Wonderful (344) "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 $114 CA $126 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Comfort Room](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/7fa649ae.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/baf4a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/47811fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monroe Street Suites Pittsfield 9.6/10 Exceptional (57) "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 $165 CA $182 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/9e5d5186.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/fcd7f602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/48a0e756.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) ### River's Edge Motel Louisiana 9.0/10 Wonderful (354) "Staff was really nice and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rhonda CA $113 CA $128 total includes taxes & fees Dec 11 - Dec 12 [](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) ![Comfort Single Room](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/f94c19c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, Italian cuisine](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/9be9497f.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) ### The Eagles Nest Inn Louisiana 9.4/10 Exceptional (19) "The room was great. Large and attractive!! Nice bathroom. Had all the convenience you need from TV to mini frig. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith CA $109 CA $123 total includes taxes & fees Nov 25 - Nov 26 [](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/b068773a.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/d2b2608d.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) ![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) ### Cozy room located in historic downtown with a 5 minute walk to the riverfront! Louisiana 10/10 Exceptional (1) "Great property. Highly recommend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan A. CA $159 CA $198 total includes taxes & fees Nov 24 - Nov 25 [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w547h683x240y0-d6fb1b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w525h683x260y0-46d39fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL Jacksonville 10/10 Exceptional (15) "This was the cutest and most relaxing a place I have ever stayed. We've so enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda B. CA $140 CA $178 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96870000/96867000/96866906/540e3d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/97000000/96870000/96867000/96866906/a9e7262d.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/97000000/96870000/96867000/96866906/ce03d1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/97000000/96870000/96867000/96866906/2e49a98a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic rooms near riverfront in downtown, Louisiana, MO Louisiana 10/10 Exceptional (1) "Very clean quaint property. Our room was situated overlooking a busy 4-way stop which made it a bit loud for sleeping when the trucks with loud mufflers rolled through but rested well just the same. Recommend this property for those looking for a quaint historic stay within walking distance to the Mighty Mississippi! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy M. CA $159 CA $187 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Louisiana-Hotels-Historic-Rooms-Near-Riverfront-In-Downtown.h96866906.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1015h683x4y0-0f291390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w907h683x58y0-a90a2146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1014h683x5y0-7d846d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville Jacksonville 10/10 Exceptional (8) "The cabin is perfect for creating a relaxing atmosphere. We always like our stay there." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James Z. CA $182 CA $223 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Jacksonville-Hotels-Audreys-Abode.h103428480.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=2025-12-07&endDate=2025-12-08®ionId=146411&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_146411) ## Top Pittsfield Hotel Reviews ## Frequently asked questions ### What are some hotels with pools in Pittsfield? > [William Watson Hotel](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information): Offers sun loungers, a pool, and complimentary wireless internet access. ### What is there to see and do in Pittsfield? > The picturesque setting of King Park showcases the area's natural beauty. During your stay, check out sights such as Pike County Historic Museum, Old Orchard Country Club, and John Greene Shastid House. ### When is the best time to book a hotel with a pool in Pittsfield? > You may want to consider a place to stay that has an outdoor pool if you're planning to visit Pittsfield in the hottest months of July, August, or June when the average temperature is 73°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 34°F. ## 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) - [Atlas Hotels](https://www.expedia.ca/Atlas-Hotels.d3000346106.Travel-Guide-Hotels) - [Lodges in Atlas](https://www.expedia.ca/Atlas-Lodges.d3000346106-aaLodges.Travel-Guide-Accommodation) - 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[Book Hotels with a Pool in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Hotels-Hotel-With-Pool.0-0-d146411-tHotelwithPool.Travel-Guide-Filter-Hotels)