Title: The Best Pittsfield Hotels with Pools from $86 - Hotels with indoor pools in Pittsfield, IL | Expedia.com [Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx146411)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.com/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.com/Cheap-Flights-To-Pittsfield.d146411.Travel-Guide-Flights)[Car Rentals in Pittsfield](https://expedia.com/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.com/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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 [Mar 11 - Mar 12](https://www.expedia.com/Hotel-Search?regionId=146411&startDate=2026-03-11&endDate=2026-03-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 12 - Mar 13](https://www.expedia.com/Hotel-Search?regionId=146411&startDate=2026-03-12&endDate=2026-03-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=146411&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=146411&startDate=2026-03-20&endDate=2026-03-22&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 ![Hallway](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/946d8e4a.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/baf4a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room | Premium bedding, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/1af516fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monroe Street Suites [](https://www.expedia.com/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 $98 nightly $108 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.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) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a47c0b8e.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) ![Standard Room, 1 King Bed, Accessible | Desk, free WiFi, bed sheets](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.com/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) Pittsfield 8.6/10 Excellent (143 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeramy $119 nightly $131 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/6afc32c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1.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) ![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) ### William Watson Hotel [](https://www.expedia.com/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 $78 nightly $86 total Mar 14 - Mar 15 Total with taxes and fees [](https://www.expedia.com/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) ![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 | Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e6a3a05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield [](https://www.expedia.com/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) Pittsfield 6.8/10 (129 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 $51 nightly $56 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/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) ![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) ![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 [](https://www.expedia.com/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.Hotel-Information) Pittsfield $332 nightly $352 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.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/13000000/12240000/12232200/12232142/0bee3acc.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 [](https://www.expedia.com/Hannibal-Hotels-Rivers-Edge-Motel.h12232142.Hotel-Information) Louisiana 9.0/10 Wonderful (360 reviews) "Staff was really nice and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rhonda $80 nightly $91 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/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) ![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/be738395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Eagles Nest Inn [](https://www.expedia.com/Louisiana-Hotels-The-Eagles-Nest-Inn.h111944656.Hotel-Information) Louisiana 9.4/10 Exceptional (21 reviews) "Room was spacious and clean. Had a great stay. The restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $96 nightly $109 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/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) ![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) ![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! [](https://www.expedia.com/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. $133 nightly $143 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/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) ![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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-bbfcfe44.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.com/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) Jacksonville 10/10 Exceptional (16 reviews) "Always a nice place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pete D. $119 nightly $126 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/9ef3ff50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/00d407ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/1abf71d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/269b2632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS! [](https://www.expedia.com/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.Hotel-Information) Bluffs 10/10 Exceptional (58 reviews) "Beautiful place, highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony S. $203 nightly $215 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.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.com/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26®ionId=146411&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Pittsfield 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.com/deals?rfrr=AFFINITY_SPRING_PROMO_146411) ## 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 - Vacation Rentals - [Hotels near Pike County Historic Museum ](https://www.expedia.com/Pike-County-Historic-Museum-Hotels.0-l553248621564478949-0.Travel-Guide-Filter-Hotels) - [Hotels near King Park ](https://www.expedia.com/King-Park-Hotels.0-l553248621564478944-0.Travel-Guide-Filter-Hotels) - [Hotels near Old Orchard Country Club ](https://www.expedia.com/Old-Orchard-Country-Club-Hotels.0-l553248621564478943-0.Travel-Guide-Filter-Hotels) - [Detroit Hotels ](https://www.expedia.com/Detroit-Hotels.d553248634983286725.Travel-Guide-Hotels) - [New Salem Hotels ](https://www.expedia.com/New-Salem-Hotels.d553248634983461930.Travel-Guide-Hotels) - 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