Title: Book the Best ROMANTIC Hotels in Winchester Historic District, Winchester from CA $151 - Winchester Historic District Romantic Getaways | Expedia.ca [Winchester Historic District Travel Guide](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester-Historic-District.d918789051029594112.Car-Rental-Guide)[Winchester Historic District Vacations](https://expedia.ca/Winchester-Historic-District.d918789051029594112.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Winchester Historic District, Winchester from CA $151 ![](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 District Romantic Hotels Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Winchester Historic District Romantic Hotels ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1004) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $177 CA $201 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/bb49c17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal Front Royal 9.0/10 Wonderful (1022) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irina CA $150 CA $167 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9874bc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1000) "Nice place. Good bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald CA $159 CA $180 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![1 bedroom, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/a3d383f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/57a6dfe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester Winchester 9.4/10 Exceptional (743) "Nice place, very quiet, comfie beds, and great staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $156 CA $170 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/eaa4b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Bamford Suite)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/50b1e67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/9aa4d92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/46449a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn Charles Town 8.6/10 Excellent (670) "We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nataliya CA $230 CA $293 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a948cd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a36008d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Winchester Winchester 8.8/10 Excellent (499) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA D CA $134 CA $151 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/6a9fc093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (500) "Great place to stay to go to the casino" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $163 CA $197 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/8c81eb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Renoir](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/ff749f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Matisse at The Villa](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/957a1979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/22bccc43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Auberge Provencale Inn & Restaurant Boyce 9.6/10 Exceptional (172) "Wonderful staff and service!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eliel Constantine CA $385 CA $425 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Winchester-Hotels-LAuberge-Provencale.h15945622.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/299522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/2f175422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/d6942b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/b112d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn Middletown 9.2/10 Wonderful (409) "Historic inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $158 CA $189 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/ec5927b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/d125a823.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/71000000/70970000/70967300/70967291/a10ded34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/91aab365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Glamper w/ Hot Tub and full bathroom-sleep 6 Capon Bridge 10/10 Exceptional (23) "We absolutely loved this place! The glamper had everything we needed and more! The hot tub was super relaxing and the host is super responsive! Would definitely stay here again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $91 CA $257 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Large-Glamper-W-Hot-Tub-And-Full-Bathroom-Sleep-6.h70967291.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=918789051029594112&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Historic District Hotel Reviews ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Parking area felt very safe. Fruit available for breakfast. " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "It was great the only thing bad .Breakfast only started at 7 am we had to leave at 6.30 am" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Wonderful stay. " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Nice place. Good bar." [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Always a great stay at this hotel. I highly recommend! " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Winchester Historic District? > If you and your partner need a romantic escape, we've got just the thing. If you'd like to explore some of the area's notable sights, you might make a stop by Bright Box Theater, Winchester Little Theater, or Shenandoah Valley Discovery Museum. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list. ### What is there to do in Winchester Historic District? > There's nothing better than experiencing a new place with your sweetheart, so consider checking out all that Winchester Historic District has to offer. 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[Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Winchester Vacations](https://www.expedia.ca/Winchester.d6056879.Destination-Travel-Guides) - [Budget Rental Cars in Winchester](https://www.expedia.ca/Budget-Car-Rentals-In-Winchester.d6056879-c39.Car-Rental-Guide-Suppliers) - [Car rental Winchester](https://www.expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide) - [National Car Rental Rental Cars in Winchester](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Winchester.d6056879-c42.Car-Rental-Guide-Suppliers) - [Winchester Vacation Rentals](https://www.expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals) - [Things to do in Winchester](https://www.expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)