Title: Book the Best Stephens City WINERY Hotels in 2025 | Expedia.ca [Hotels in Stephens City](https://expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels)[Vacation Rentals in Stephens City](https://expedia.ca/Stephens-City-Vacation-Rentals.d12076.Travel-Guide-VacationRentals)[Stephens City Car Rentals](https://expedia.ca/Car-Rentals-In-Stephens-City.d12076.Car-Rental-Guide)[Stephens City Vacation Packages](https://expedia.ca/Stephens-City.d12076.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/4eb3a138bbc7379d95be69b627036ee2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Stephanie Sutton # Find Winery Hotels in Stephens City, VA from CA $90 ![](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 Stephens City Winery Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=12076&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=12076&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=12076&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=12076&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Stephens City Winery Hotels ![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) ![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) ![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) ### Hampton Inn Front Royal Front Royal 9.0/10 Wonderful (1007) "convenient to Shenandoah Park" CA $154 CA $171 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/a2451115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/c5b2135d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/ff7a3bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Front Royal Near Shenandoah National Park Front Royal 6.4/10 (891) "nice for a great stay!!" CA $81 CA $90 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG Winchester 9.0/10 Wonderful (1007) "Great stay value" CA $109 CA $123 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/06bbe3a4.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) ### Wayside Inn Middletown 9.2/10 Wonderful (407) "Clean room and friendly staff. Air conditioning was very noisy and the inn needs some upkeep, but we would stay there again." CA $156 CA $187 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester Winchester 9.4/10 Exceptional (737) "Great location clean facilities " 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) ![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/ec5927b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/57af18f8.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) ### Large Glamper w/ Hot Tub and full bathroom-sleep 6 Capon Bridge 10/10 Exceptional (23) "The listing was exactly as described and we thoroughly enjoyed are stay. It was a great date night escape for the night that was too far from home. I will rent again. " CA $100 CA $267 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Large-Glamper-W-Hot-Tub-And-Full-Bathroom-Sleep-6.h70967291.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/beb9f8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/0a99747a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/630d5570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/d6ab4bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes! Harpers Ferry 10/10 Exceptional (5) CA $175 CA $508 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.Hotel-Information) ![Premier Villa, 1 King Bed, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/a36aa267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/12f25c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/445f5296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed, Non Smoking (The Cottage)](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/4c371a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White Moose Inn Washington 9.8/10 Exceptional (145) "Amazing trip! " [](https://www.expedia.ca/Washington-Hotels-White-Moose-Inn.h13390991.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) ![Exterior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x60y0-c1839f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/07522565.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 (8) "Host communicated well. Great location right on the river. Family had a great time. " CA $250 CA $510 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Charles-Town-Hotels-The-River-House.h114349198.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/83125d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/450f7eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/0c480063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/5879ce85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Red Schoolhouse Cross Junction 9.8/10 Exceptional (11) "We loved the overall school house theme. Very comfortable accommodations! " CA $127 CA $297 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Cross-Junction-Hotels-The-Little-Red-Schoolhouse.h98495723.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=2025-10-26&endDate=2025-10-27®ionId=12076&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Stephens City 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 "Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Days Inn by Wyndham Charles Town/Harpers Ferry](//images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/6feea908_y.jpg) ### Days Inn by Wyndham Charles Town/Harpers Ferry 10/10 Excellent "Nice place to stay" [](https://expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.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 "Great location." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Quality Inn Stephens City - Winchester South](//images.trvl-media.com/lodging/1000000/10000/4500/4419/9730f3d8_y.jpg) ### Quality Inn Stephens City - Winchester South 10/10 Excellent "Everything here is very nice I love the outdoor fire pit gas of course. Very inviting! The Staff is excellent and the area very convienent! The breakfast very well thought out and a variety to be had! If you need Anything just ask, washer and dryers complimentary and lots of shopping around! Plus an indoor pool! I say yes! I need another stay to enjoy! " [](https://expedia.ca/Winchester-Hotels-Quality-Inn-Stephens-City-Winchester-South.h4419.Hotel-Information) ![Holiday Inn Express Charles Town by IHG](//images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg) ### Holiday Inn Express Charles Town by IHG 10/10 Excellent "One of the best facilities we've ever used." [](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Holiday Inn Express Woodstock-Shenandoah Valley by IHG](//images.trvl-media.com/lodging/1000000/30000/20600/20598/e45798f9_y.jpg) ### Holiday Inn Express Woodstock-Shenandoah Valley by IHG 10/10 Excellent "Awesome " [](https://expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.Hotel-Information) ![Holiday Inn Express Winchester South-Stephens City by IHG](//images.trvl-media.com/lodging/1000000/40000/34400/34394/4d102079_y.jpg) ### Holiday Inn Express Winchester South-Stephens City by IHG 10/10 Excellent "always a pleasure to stay here. checkin and out is flawless. staff are very friendly." [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.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 "Great stay!" 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[Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [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) - 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