Title: Book the Best ADVENTURE Hotels in Old Town Winchester in 2025 | Expedia.ca [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)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Old Town Winchester, VA from CA $141 - ![](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 Old Town Winchester Hotels & Resorts for Couples Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6164092&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=6164092&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Winchester Hotels & Resorts for Couples ![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) ![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) ![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) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1007) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $177 CA $201 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.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/w3837h2557x3y3-0ba96f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal Front Royal 9.0/10 Wonderful (1029) "Well located and very clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Odile CA $157 CA $175 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/fb0da257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Winchester Winchester 9.0/10 Wonderful (782) "Super friendly staff, clean rooms, very convenient. I would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $130 CA $141 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x59y0-9f28244e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x60y0-4183e173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x60y0-c1839f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w506h683x259y0-56e475a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The River House Charles Town 10/10 Exceptional (9) "Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey W. CA $142 CA $383 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Charles-Town-Hotels-The-River-House.h114349198.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/32a5f0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/928d407e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Bungalow in Front Royal Front Royal 10/10 Exceptional (7) "Excelente propiedad " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Miguel CA $189 CA $309 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/be60c3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One king study sofabed non smoking](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/311c50f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/e77a1d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA Winchester 9.2/10 Wonderful (830) "Great place to stay. Super clean and comfortable beds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy Allen CA $148 CA $168 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/800932de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/16920465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/769f9c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area Winchester 9.0/10 Wonderful (1005) "Free Breakfast and parking. Close to many restaurants and shops" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vijaypal CA $148 CA $168 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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=2025-11-17&endDate=2025-11-18®ionId=6164092&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester Hotel Reviews ![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 "Very courteous. Only problem is lack of outlets near the bed. " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Rodeway Inn & Suites - Charles Town, WV](//images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662_y.jpg) ### Rodeway Inn & Suites - Charles Town, WV 10/10 Excellent "The carpet was old and stained up. Low dingy, but the room overall was clean. Bathroom was clean." [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.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 "Service was great!!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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 "We had a pleasant stay, staff was really nice and the room was spotless. Easy check in, the breakfast in the morning was enjoyable. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "The staff was amazing! As we zipped in and out we were always welcomed or wished a good day. Big smiles and just super nice! Loved the coffee/tea area. Talk about coming home. My one comment would be that the trash cans were never emptied in our room or bathroom. And because the cans are so small by end of day two they were overflowing. When the gal came to do our room we were just getting ready to leave and she said she couldn’t come in while guests were in the room. (Think that is a good safety concept for both her and guests.). So we told her we were leaving almost immediately and could she please empty our trash. Never came in as trash remained over flowing. When checking out Monday morning I mentioned this and the woman at the desk said “next time just put the trash outside your room in the hallway.” My comment is “When paying as much as was for stay of three nights - your trash cans should definitely be emptied!” All in all can not say enough about the quality and helpfulness of all the rest of the staff. Excellent group! " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![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 "TV wasn’t in high definition. Could have been better." [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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 "The entire property was very clean and the staff extremely friendly." [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "Not really a good breakfast area or food to choose from. The beds are hard the pillows are terrible plus the sheets had stains. The tvs are old and like only 5 channels to watch. Walls are thin " [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "Good" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ## Frequently asked questions ### Why book your hotel for couples in Old Town Winchester with Expedia? > We believe that a trip with your sweetheart should be a breeze, so if you're in search of a hotel for couples in Old Town Winchester at a competitive price, Expedia has you covered. Stick to the budget and choose a low-cost motel, or splurge and book a plush hotel break to surprise the one you love the most. ### How can I find cheap hotels for couples in Old Town Winchester? > With Expedia's handy filter tool, getting your hands on cheap hotels for couples in Old Town Winchester couldn't be simpler. 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