Title: TOP Casino Hotels in Winchester, VA for 2025 | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d6056879.Travel-Guide-HolidayRentals)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d6056879.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d6056879.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Casino Hotels in Winchester ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](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 Casino Hotels Tonight [12 Oct - 13 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [13 Oct - 14 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-13&endDate=2025-10-14&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Casino Hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/917000/916960/6f69452b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout curtains, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/920000/917000/916960/98533a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/917000/916960/8580746a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout curtains, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/920000/917000/916960/586edd44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Winchester VA Winchester 6.2/10 (611) "Kind professionals" £47 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/Winchester-Hotels-Super-8-By-Wyndham-Winchester-VA.h916960.Hotel-Information) ![Casino](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/90e3a6e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/cba53522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/1054ff00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn Harpers Ferry - Charles Town Harpers Ferry 8.0/10 Very good (1013) "A good, clean, comfortable stay " £77 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/45f48b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/878c91bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/e6df8eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Martinsburg Martinsburg 8.6/10 Excellent (932) "Good breakfast, great helpful staff" £86 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![2 bars/lounges, sports bar](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/64e72433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Smoking | Desk, iron/ironing board, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/71615746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/14125876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites - Charles Town, WV Charles Town 8.6/10 Excellent (1007) "It is a very good place to stay " £61 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/9c1d9621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/1a9ef301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/3c5b5f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️ Secluded 1940s Romantic Tiny House on the River Shepherdstown 10/10 Exceptional (61) "We truly loved this location and definitely will be back!" £82 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.Hotel-Information) ![Casino](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/d7ac3540.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) ![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) ![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 (497) "It is convenient to the casino and racetrack. The continental breakfast was average at best. For a tremendous breakfast try the Charlestown Family Diner across the street from this property." £108 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/cf8a1df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/6bf5690d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/00037a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/a62a4c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cabin in the Woods with River Access Shepherdstown 9.6/10 Exceptional (36) "Very quiet and cozy property. Well maintained and nice location." £225 includes taxes & fees 23 Oct - 24 Oct [](https://www.expedia.co.uk/Shepherdstown-Hotels-Charming-Cabin-In-The-Woods-With-River-Access.h100779583.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) ![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) ![Interior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/630d5570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/f0a9c087.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) £277 includes taxes & fees 5 Nov - 6 Nov [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/w4000h2999x0y0-c4e30b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/570094cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/fe693219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/7f46c199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage on King | Charming Historic Leesburg Home Leesburg 9.6/10 Exceptional (59) "Charming cottage within walking distance of great restaurants in Leesburg. Enjoyed a quiet weekend away and evening strolls through the neighborhood. " £235 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Leesburg-Hotels-Cottage-On-King-Charming-Historic-Leesburg-Home.h50679492.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/6f99e56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Mary Rutherford Room | Individually decorated, individually furnished, blackout curtains](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/fead0911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/acf14b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Inn B&B Charles Town 9.6/10 Exceptional (429) "Excellent accommodations and breakfast. " £133 includes taxes & fees 30 Oct - 31 Oct [](https://www.expedia.co.uk/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.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.co.uk/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27®ionId=6056879&adults=2&amenities=CASINO&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Winchester ### Discover top Winchester attractions While Winchester, Virginia may not boast casinos, it offers an array of attractions that can appeal to travellers seeking a thrilling experience. For history enthusiasts, the Museum of the Shenandoah Valley can captivate with its extensive collection of American art and history, making it a perfect day trip to soak in the local culture. Outdoor adventurers can explore the scenic trails of the nearby Shenandoah National Park, where you can hike and enjoy breathtaking views, adding a touch of excitement to your stay. For a unique evening out, the vibrant downtown area features several local breweries and restaurants, where you can indulge in craft beers and delicious cuisine while soaking in the local atmosphere. The historic Old Town is dotted with charming shops, offering an eclectic mix of antiques and artisanal goods, perfect for a leisurely afternoon stroll. Finally, for those seeking a more adrenaline-fuelled experience, the nearby Shenandoah Speedway hosts various racing events, providing a thrilling experience just a short drive away. When it comes to accommodation, the hotels in and around Old Town Winchester offer a blend of comfort and charm, allowing you to unwind after a day of exploring. Many establishments pride themselves on exceptional service, ensuring your stay is pampered and relaxed, with convenient access to all the local attractions. ## Top Winchester Hotel Reviews ![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 "2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. " [](https://expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### Searching for casino hotels in Winchester? > If you're heading to Winchester for some gaming, you can roll the dice at Hollywood Casino at Charles Town Races, located 18.5 mi (29.8 km) away, but it's not the only place to visit while you're in town. Tourists speak highly of the historic landmarks, shopping and local cuisine. ### How many hotels that are good for gaming will I find in Winchester? > Get your game on at one of Expedia's 79 hotels in Winchester. ### When should I take my casino trip to Winchester? > You might spend a lot of your holiday inside, but if you're planning to venture beyond the casino, looking at local weather trends is a good idea. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm. ### What is there to do in Winchester? > You can head to Apple Blossom Mall, Apple Valley Square Shopping Center or Northpark Shopping Center to shop for the perfect souvenir. Winchester is known for its historic sites, theatres and entertainment venues, and you can visit cultural spots such as Winchester Little Theater and Museum of the Shenandoah Valley. In addition, you might want to visit Bright Box Theater and Shenandoah Valley Discovery Museum. ### What are my transportation options for my casino getaway to Winchester? > Here are some transportation options in Winchester: You can fly into the nearest airport, which is Martinsburg, WV (MRB-Eastern West Virginia Regional), 18 mi (28.9 km) from the city centre. 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[Flights from Chicago (ORD) to Winchester (WGO)](https://www.expedia.co.uk/lp/flights/ord/wgo/chicago-to-winchester) - [Apple Blossom Mall](https://www.expedia.co.uk/Apple-Blossom-Mall-Winchester.d6164018.Attraction) - [Barns of Rose Hill](https://www.expedia.co.uk/Barns-Of-Rose-Hill-Berryville.d553248621561864687.Attraction) - [Berryville Holidays](https://www.expedia.co.uk/Berryville.d184082.Holidays-City-Breaks) - [Visit Bluemont](https://www.expedia.co.uk/Bluemont.dx6348602) - [Boyce Holidays](https://www.expedia.co.uk/Boyce.d184084.Holidays-City-Breaks) - [Bright Box Theater](https://www.expedia.co.uk/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Attraction) - [Dinosaur Land](https://www.expedia.co.uk/Dinosaur-Land-White-Post.d553248621532661835.Attraction) - [Visit Front Royal](https://www.expedia.co.uk/Front-Royal.dx7312) - [Visit Linden](https://www.expedia.co.uk/Linden.dx3000460101) - [Mackintosh Fruit Farm](https://www.expedia.co.uk/Mackintosh-Fruit-Farm-Berryville.d553248621532661930.Attraction) - 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