Title: Book the Best Hotels with BARS 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 Bar in Pittsfield, IL from CA $93 ![](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 Bar ## Top Pittsfield Hotels with Bar We don't have any properties that match your exact search [See all properties in Pittsfield](https://expedia.ca/Hotel-Search?startDate=2025-11-06&endDate=2025-11-07®ionId=146411&adults=2) ## Recommended hotels in Pittsfield ![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 (57) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake CA $164 CA $180 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![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) ![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) ### Green Acres Hotel Pittsfield 8.6/10 Excellent (139) "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 $166 CA $183 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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/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) ### William Watson Hotel Pittsfield 9.2/10 Wonderful (341) "Great place to stay! Brandi is the best." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $125 CA $138 total includes taxes & fees Oct 31 - Nov 1 [](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) ![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) ![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 (121) "I could not check in because the clerk never showed up to check us in. 2 hours at least with two trips to the site and 3 phone calls. I could not get anyone to talk to or check us in. I left a message that we were cancelling and we went to another motel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $84 CA $93 total includes taxes & fees Nov 19 - Nov 20 [](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) ![Golf](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/9aafb100.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 Pittsfield CA $351 CA $492 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.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) ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/70ba5f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake. Pittsfield CA $338 CA $474 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Pittsfield-Hotels-Lovers-Lakeside-Love-Nest-Cozy-Retreat-On-Pittsfields-Serene-Lake.h109522338.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 (349) "Clean,quiet, easy parking and great view of the river." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $112 CA $127 total includes taxes & fees Oct 24 - Oct 25 [](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) ![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) ![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 (18) "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 $131 CA $149 total includes taxes & fees Nov 23 - Nov 24 [](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) ![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) ### 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 $157 CA $185 total includes taxes & fees Oct 30 - Oct 31 [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w547h683x240y0-d6fb1b93.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy M. CA $139 CA $176 total includes taxes & fees Oct 31 - Nov 1 [](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=2025-11-06&endDate=2025-11-07®ionId=146411&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![William Watson Hotel](//images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg) ### William Watson Hotel 10/10 Excellent "Great place to stay! Brandi is the best." [](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Pittsfield? > Though you might not find a hotel in Pittsfield well-known for its bar, you will find 10 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're here, consider a visit to Old Orchard Country Club and Pike County Historic Museum. ### What is there to do in Pittsfield? > If you have time to explore, consider visiting Old Orchard Country Club, Clarksville Riverfront Park, and Mississippi River, and then find a cozy spot for a nightcap. Other places to see include Pike County Historic Museum and John Greene Shastid House. ### When is the best time to visit Pittsfield? > Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you decide the best time for bar hopping. The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Pittsfield is 46 inches. ### How can I get to Pittsfield and around the area? > You might want to make the most of these transportation options in and around Pittsfield: Fly into Quincy, IL (UIN-Quincy Regional-Baldwin Field), which is located 30.6 mi (49.3 km) from the heart of the city. 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