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) ![](https://mediaim.expedia.com/destination/1/20ffc1c1fd9890df2c042f65a516b89f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Pittsfield, IL from CA $97 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Hotels with a Pool We don't have any properties that match your exact search [See all properties in Pittsfield](https://expedia.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23®ionId=146411&adults=2) ## 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) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a47c0b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/7da0a008.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) ### Green Acres Hotel Pittsfield 8.6/10 Excellent (139) "Wonderful stay - was staying with a number of family members and it all worked out" CA $166 CA $183 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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/baf4a218.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) ![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) ### Monroe Street Suites Pittsfield 9.6/10 Exceptional (56) "Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future." CA $164 CA $180 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8fabc5ce.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) ### William Watson Hotel Pittsfield 9.2/10 Wonderful (337) "Its a lovely hotel " CA $125 CA $138 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.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/6000000/5640000/5637500/5637460/74c9995c.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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e9aab2d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield 6.8/10 (120) "They really should attach the drain cover to the shower drain. Somebody could get seriously injured. Being a tile guy, looking around really had me laughing at the workmanship. The manager was a pretty cool guy, the room was fine, air conditioner worked great. Never went to the continental breakfast, i did see some little Debbie items" CA $88 CA $97 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/2e31b21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/9bcffa95.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) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/w1079h1437x0y3-b96511c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake. Pittsfield CA $336 CA $472 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Pittsfield-Hotels-Lovers-Lakeside-Love-Nest-Cozy-Retreat-On-Pittsfields-Serene-Lake.h109522338.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) ![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1080h1437x0y3-5f7123c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-36d6779a.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) ### Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland Pittsfield CA $350 CA $491 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/c1c872f1.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) ### River's Edge Motel Louisiana 9.0/10 Wonderful (346) "Clean,quiet, easy parking and great view of the river." CA $112 CA $127 total includes taxes & fees Oct 9 - Oct 10 [](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) ![Exterior](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/2c8ee78f.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) ![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) ### The Eagles Nest Inn Louisiana 9.6/10 Exceptional (15) "The room was great. Large and attractive!! Nice bathroom. Had all the convenience you need from TV to mini frig. " CA $130 CA $148 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Louisiana-Hotels-The-Eagles-Nest-Inn.h111944656.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) ![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) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/97000000/96870000/96867000/96866906/15f4aff6.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! " CA $157 CA $185 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Louisiana-Hotels-Historic-Rooms-Near-Riverfront-In-Downtown.h96866906.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) ![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) ![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 (14) "Wonderfully peaceful with a little wildlife added for fun. " CA $138 CA $176 total includes taxes & fees Oct 12 - Oct 13 [](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=2025-10-22&endDate=2025-10-23®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? > [William Watson Hotel](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information): Features 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 Old Orchard Country Club, Pike County Historic Museum, 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)