Title: Book the Best HISTORIC Hotels in Winchester in 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6046207.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6046207.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 Historic Hotels in Winchester, IN from CA $74 - ![](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 Winchester Historic Hotels Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Historic Hotels We don't have any properties that match your exact search [See all properties in Winchester](https://expedia.ca/Hotel-Search?startDate=2025-11-18&endDate=2025-11-19®ionId=6046207&adults=2) ## Recommended hotels in Winchester ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/77a3466c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/c679c171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/fee1facc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/w992h749x8y1-a775c4b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Randolph Inn and Suites Winchester 9.0/10 Wonderful (241) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William [](https://www.expedia.ca/Muncie-Hotels-Randolph-Inn-And-Suites.h1778532.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/d689bf19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/63004fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/8c4791db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/b30bf8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Richmond 9.4/10 Exceptional (626) "Very clean and quiet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $127 CA $146 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Richmond-Hotels-Comfort-Suites.h92418479.Hotel-Information) ![Food court](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/451c7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/0c112d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d0795775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Richmond Indiana I-70 Richmond 8.4/10 Very good (1004) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff CA $131 CA $147 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/19000000/18590000/18585800/18585726/c77afba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/19000000/18590000/18585800/18585726/82366043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds | Bathroom](https://images.trvl-media.com/lodging/19000000/18590000/18585800/18585726/e4e5c641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds](https://images.trvl-media.com/lodging/19000000/18590000/18585800/18585726/b5bb3dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Golden Inn New Paris 9.2/10 Wonderful (431) "Wonderful place to stay, clean rooms and quiet, very comfortable, would stay here again so nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee CA $103 CA $116 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Dayton-Hotels-The-Golden-Inn.h18585726.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/3e0f69fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/bd1ec505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/a66e4fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/f850563e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Richmond, IN Richmond 7.8/10 Good (977) "Great to be able to walk to food and get great food" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlene CA $73 CA $82 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/b66d8027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible (Comm, Mobil, Roll-In Shower)](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/267bdaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/4394c4fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/02bf683d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Portland by IHG Portland 9.2/10 Wonderful (348) "Excellent stay every time we are there friendly staff all around awesome stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $146 CA $163 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Muncie-Hotels-Holiday-Inn-Express-Suites-Portland.h1880898.Hotel-Information) ![Room, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/74d1da02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/e2971d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/2d4f8dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/6cefc466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Greenville North Greenville 8.2/10 Very good (340) "Friendly staff, clean quiet room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $143 CA $162 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Sidney-Hotels-Quality-Inn-Greenville-North.h60521.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18000/17932/c96cf457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/18000/17932/1f84cabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Smoking](https://images.trvl-media.com/lodging/1000000/20000/18000/17932/30f2512a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, soundproofing](https://images.trvl-media.com/lodging/1000000/20000/18000/17932/378147c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Richmond Inn & Suites Richmond 7.0/10 Good (353) "A good value for a one night stay. Nothing fancy, but quiet and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $47 CA $74 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Richmond-Hotels-Richmond-Inn-Suites.h17932.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/f7718af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/57d10bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/619f2889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/56a546ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn by Marriott Richmond New Paris 9.0/10 Wonderful (511) "Front desk Evonne was courteous and helpful especially after I had been driving all day at it was 11:00 pm! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $142 CA $161 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Dayton-Hotels-Fairfield-Inn-By-Marriott-Richmond.h52875.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/53012ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/f73ddc6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/3f1c5502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Sofabed)](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/127e8ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surestay By Best Western Greenville Greenville 7.8/10 Good (379) "The faucet was coming out of the wall. There were bugs coming out of the bathroom sink. The sheets were stained. For the rates they’re expecting, it needs work. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawna CA $130 CA $147 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Greenville-Hotels-Surestay-By-Best-Western-Greenville.h5248460.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=2025-11-18&endDate=2025-11-19®ionId=6046207&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Best Western Plus Richmond Indiana I-70](//images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730_y.jpg) ### Best Western Plus Richmond Indiana I-70 10/10 Excellent "In 2025, the nearby construction is getting close to finished, but there were no noise or dust issues and the hotel was very nice and very clean. I’d stay there again any time." [](https://expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Hampton Inn & Suites Richmond, IN](//images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/1e53a5db_y.jpg) ### Hampton Inn & Suites Richmond, IN 10/10 Excellent "Clean room" [](https://expedia.ca/Richmond-Hotels-Hampton-Inn-Suites-Richmond.h1590037.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Winchester? > Significant historical sites in Winchester are likely at the top of your sightseeing list. While you're in town, why not also enjoy the many sights including the golf courses? ### How many historical hotels are there in Winchester? > In Winchester, there are 2 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the top historical sites and other places to visit in Winchester? > A couple of favorite places to visit are Winchester Golf Club and Winchester Speedway. You'll also find Prairie Creek Reservoir and Campground and Darke County Fairgrounds in the area. ### What is a historic hotel like in Winchester? > When you choose a historic hotel, you'll sleep someplace that has an officially recognized national historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be considered a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the guestrooms or communal spaces of such hotels in Winchester, bringing the history to life. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The architecture and actual building of a historic hotel is generally the most important aspect. For a heritage hotel, often it's the cultural value along with how it inspired the community. ### Do historic hotels in Winchester have modern facilities? > Hotels include modern conveniences and safety features you might expect, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, free WiFi, and the usual amenities found in a hotel should be available at a historic hotel. 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