Title: Book the Best Winchester WINERY Hotels in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[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 Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Winery Hotels Tonight [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-21&endDate=2026-01-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-22&endDate=2026-01-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels with winery ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/54c3ac5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/6c4fd659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/40efde4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) Front Royal 9.0/10 Wonderful (1,002 reviews) "Very nice breakfast (eggs sausage, potatoes, ...), clean lobby, and all the staff was friendly, including Beatrix. Also we appreciated the attention to a clean and warm pool room on a very cold January. Great mexican 1 mile away at Potrillo's." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kenneth CA $135 CA $150 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/8a97ffc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/67555e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/636f5ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (799 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene CA $148 CA $161 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/a3d72fc4.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) ![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) ![Point of interest](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/9e80fe83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) Middletown 9.2/10 Wonderful (420 reviews) "Historic inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $100 CA $124 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.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 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1,000 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $108 CA $122 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/e4739be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/ccd121a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/234bd7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/0b0b85aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury tiny home farm stay on historic property with hot tub in Stephens City [](https://www.expedia.ca/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information) Stephens City 10/10 Exceptional (1 review) "Fresh bread, farm eggs, an amazing host! What a perfect place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris F. CA $181 CA $227 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/d80b6458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain Top hot tub overlooking the Shenandoah River [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) Front Royal 10/10 Exceptional (11 reviews) "Our family had a lovely time at The Vue! It was clean, comfortable, and had everything we needed for a quick getaway. The mountain view was truly incredible and we enjoyed watching the sunrise with our coffee on the back deck. While there's not much of a yard, our pup enjoyed the outdoor space too! Thank for being a part of our family's special memories. We'll be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa L. CA $128 CA $471 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/92815ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/f9fe7afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/435bb49d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/16f6f354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Mountain Cabin, secluded, perfect for couples, near main road [](https://www.expedia.ca/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information) Front Royal 10/10 Exceptional (27 reviews) "Great place to relax" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judy CA $249 CA $314 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information) ![Winery](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/79eb6aef.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/25f6542c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/03d5d9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Front Royal Near Shenandoah National Park [](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) Front Royal 6.4/10 (925 reviews) "Staff was very kind! Had a nice time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rio Ashley CA $76 CA $85 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b26f42f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/2f99002c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/dce8d0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b64b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall [](https://www.expedia.ca/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information) Winchester Historic District 8.6/10 Excellent (4 reviews) "Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) matthew r. CA $191 CA $324 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/13764d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/fa4984f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/2e3f9865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/9d72428f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Bluemont Village Home [](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.Hotel-Information) Bluemont 10/10 Exceptional (39 reviews) "This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary S. CA $219 CA $599 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.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=2026-02-04&endDate=2026-02-05®ionId=6056879&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg) ### Lansdowne Resort and Spa 10/10 Excellent "The resort was in great condition and very clean. The food at Coton & Rye was good for the price. Service throughout the weekend was excellent. " [](https://expedia.ca/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "yes, room was spotless very nice place to stay" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg) ### Hilton Garden Inn Dulles North 10/10 Excellent "Everything was great" [](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "It was all totally smooth " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Salamander Resort And Spa](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/21ca3455_y.jpg) ### Salamander Resort And Spa 10/10 Excellent "Great " [](https://expedia.ca/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information) ## Explore a world of travel with Expedia - 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