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 $96 - ![](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=2025-11-19&endDate=2025-11-20®ionId=146411&adults=2) ## Recommended hotels in Pittsfield ![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/7000000/6660000/6659600/6659525/23a03799.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) ### William Watson Hotel Pittsfield 9.2/10 Wonderful (344) "Small town feel, felt safe walking around at all times of the day. Was in town for a wedding and the location was perfect. AC worked great and beds were comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie 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/18000000/17050000/17047300/17047233/47811fea.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/18000000/17050000/17047300/17047233/873e4e0b.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 $165 CA $181 total includes taxes & fees Nov 16 - Nov 17 [](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) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/7da0a008.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) ![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 (140) "Best room for the price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $209 CA $230 total includes taxes & fees Nov 16 - Nov 17 [](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) "Quick easy check-in, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $88 CA $96 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) ![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) ### Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland Pittsfield CA $353 CA $495 total includes taxes & fees Nov 7 - Nov 8 [](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) ![Interior](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/9bcffa95.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 $378 CA $523 total includes taxes & fees Nov 30 - Dec 1 [](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) ![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) ![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/13000000/12240000/12232200/12232142/48a0e756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River's Edge Motel Louisiana 9.0/10 Wonderful (350) "Clean,quiet, easy parking and great view of the river." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $119 CA $136 total includes taxes & fees Nov 22 - Nov 23 [](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 (18) "Clean. Big bathroom. Bed squeaky. Walkable to river and some eating spots. It is full of history and the building was renovated beautifully. There were no common spaces to sit, it would be nice to have that outside of room 11. We would return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $130 CA $148 total includes taxes & fees Nov 13 - Nov 14 [](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/97000000/96130000/96126600/96126590/8a5e60e5.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/97000000/96130000/96126600/96126590/22ecf069.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 $158 CA $197 total includes taxes & fees Nov 6 - Nov 7 [](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) ![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) ![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 Jacksonville 10/10 Exceptional (15) "My 2nd stay! I stayed here about 6weeks prior, enroute to visit my daughter at Mizzou. It was so nice that I decided to stay again on my way to her graduation. It was perfect again! It was warm and beautiful in the morning so I even used the outdoor tub." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly W. CA $139 CA $177 total includes taxes & fees Nov 11 - Nov 12 [](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=2025-11-19&endDate=2025-11-20®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 "Everything about our stay was great. We will stay here again. The parking was good, as it was in front of the building. The restaurant was excellent." [](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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