Title: Hotels by Independent in Winchester from CA $155 | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx3000435714)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d3000435714.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000435714.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000435714.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels by Independent in Winchester from CA $155 ![](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 prices for these dates Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Independent Hotels ![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) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/7da0a008.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 $251 CA $276 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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) ![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) ![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 $177 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.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) ![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) ![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) ### 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 $181 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/64356a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/0778f0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/09335ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/fff007e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa DeWolf Jacksonville 10/10 Exceptional (10) "If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Catherine CA $347 CA $395 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Jacksonville-Hotels-Villa-DeWolf.h76952694.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/0aadb1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/18301817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/64202e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/0a889b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful studio retreat surrounded by prairie, wildlife, and open skies. Murrayville 10/10 Exceptional (25) "We had a great stay. The environment is just cuddling. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $156 CA $195 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Native-Prairie-Setting-Pets-Allowed.h22120643.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/3f150da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/8790074c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/90-68a15fb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/90-1f6f1b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods! Griggsville 9.8/10 Exceptional (80) "We had the best time staying here. My family of 20 stayed for 3 days and this place was perfect for our trip. The house was large enough to accommodate everyone comfortably and we had everything we needed. The pool area is awesome - everyone had an amazing time from the 2 year old to my 70 year old dad. A great place for kids. Communication was great and the owners were friendly and very helpful. Hope to come back again some day! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alison B. [](https://www.expedia.ca/Pittsfield-Hotels-PICKLEBALL.h34582445.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) ![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 $352 CA $493 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101230000/101225900/101225898/559ff3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/102000000/101230000/101225900/101225898/c7e7b010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101230000/101225900/101225898/6e48232c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101230000/101225900/101225898/4d20a347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upgraded farmhouse between Springfield Illinois and St.Lous Missouri Pittsfield 4.0/10 (1) "Host double booked over me for his “private” hunting business. Couldn’t use living room or kitchen because his other guests had all their hunting gear in them. My bed collapsed the second day. Real nightmare. I would never recommend this property to anyone. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip S. [](https://www.expedia.ca/Pittsfield-Hotels-Upgraded-Farmhouse-Between-Springfield-Illinois-And-StLous-Missouri.h101225898.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/269b2632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/7adb2ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/3b40112f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/60663cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS! Bluffs 10/10 Exceptional (58) "We enjoyed our stay at this beautiful country home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea C. CA $251 CA $305 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/601e94c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/270-0cf1fa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/w3096h4111x0y17-1e7de191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. Murrayville 9.8/10 Exceptional (58) "Exactly what we needed. Peaceful, secluded, and relaxing! The trails are an added bonus. The respect for nature, pets, and people spoke to us, which are evident in the aesthetic of the property. We come to Jacksonville often and will definitely be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $118 CA $155 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.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=2025-11-05&endDate=2025-11-06®ionId=3000435714&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels-Independent.0-0-d3000435714--bIndependent.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels-Independent.0-0-d3000435714--bIndependent.Travel-Guide-Filter-Hotels) ## Top Winchester 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) ![Hampton Inn Jacksonville](//images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 10/10 Excellent "My stay was great! Relaxing after a full day of work. But the best part of the trip was how wonderful your staff treated me! Madison was awesome and so kind! She offered great advice on local sites, restaurants and answered my queries with great enthusiasm. I missed her on her days off! So glad she was at the front desk the day I checked in! Also, I met another lady while staying here and we are now friends! See the attached picture of all of us… " [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.](//images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c_y.jpg) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. 10/10 Excellent "We had such a great experience staying here. The property was beautiful and the hosts were very welcoming and friendly. The property was very pet friendly as well. We will definitely go back for the peace and quiet!" [](https://expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information) ![Super 8 by Wyndham Jacksonville](//images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg) ### Super 8 by Wyndham Jacksonville 10/10 Excellent "appreciate that they always give us early check-in." [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Best Western Jacksonville Inn](//images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 10/10 Excellent "Clean and comfortable room and nice pool " [](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![Sleep Inn & Suites](//images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "Breakfast variety of healthy options Room clean" [](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Quality Inn Jacksonville near I-72](//images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg) ### Quality Inn Jacksonville near I-72 10/10 Excellent "Easy check in and out very personable and friendly staff" [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](//images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 10/10 Excellent "Didnt make it to breakfast but could still obtain banana and yoghurt. This was super nice of them. Had kecard glutch but Chris the evening desk man literally ran upstairs after rescanning ours to check that it worked. Beds were very comfy. Wood surfaces were a little worn...a minor flaw." [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!](//images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/3f150da0_y.jpg) ### PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods! 10/10 Excellent "Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. " [](https://expedia.ca/Pittsfield-Hotels-PICKLEBALL.h34582445.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Cars - More ways to book - [Alsey Hotels](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [Apartments in Arcadia](https://www.expedia.ca/Arcadia-Apartments.d553248635975871406-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Arenzville](https://www.expedia.ca/Arenzville-Cabins.d3000346095-aaCabins.Travel-Guide-Accommodation) - [Arenzville Hotels](https://www.expedia.ca/Arenzville-Hotels.d3000346095.Travel-Guide-Hotels) - [Drury Inn & Suites Hotels in Belleville](https://www.expedia.ca/Belleville-Hotels-Drury-Inn-Suites.0-0-d55581--bDruryInnSuites.Travel-Guide-Filter-Hotels) - [Four Seasons Hotels in Belleville](https://www.expedia.ca/Belleville-Hotels-Four-Seasons.0-0-d55581--bFourSeasons.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Belleville](https://www.expedia.ca/Belleville-Hotels-Hilton-Hotels.0-0-d55581--bHiltonHotels.Travel-Guide-Filter-Hotels) - 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