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://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.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 [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-27&endDate=2025-11-28&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Nov - 29 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-28&endDate=2025-11-29&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-12-05&endDate=2025-12-07&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/1000000/920000/917000/916960/586edd44.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/1000000/920000/917000/916960/98533a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Winchester VA Winchester 6.2/10 (619) "Very limited, bread , butter , jam" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Susan £47 includes taxes & fees 22 Dec - 23 Dec [](https://www.expedia.co.uk/Winchester-Hotels-Super-8-By-Wyndham-Winchester-VA.h916960.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) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/e6df8eb6.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) ![Desk, iron/ironing board, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/84e63605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Martinsburg Martinsburg 8.6/10 Excellent (979) "Good breakfast, great helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce £71 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.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 7.8/10 Good (1009) "Nice convenient hotel. Clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason £75 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/56958e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites - Charles Town, WV Charles Town 8.6/10 Excellent (1004) "I loved how clean the hotel was the check-in process was easy and even the people working upfront or super nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul £54 includes taxes & fees 11 Dec - 12 Dec [](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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/80506691.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) ![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 (64) "We truly loved this location and definitely will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Astrid £82 includes taxes & fees 8 Dec - 9 Dec [](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) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.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 (514) "Staff was courteous….helpful…room was clean and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £219 includes taxes & fees 19 Dec - 20 Dec [](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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/335684a7.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) ### Charming Cabin in the Woods with River Access Shepherdstown 9.6/10 Exceptional (39) "My family enjoyed our stay at the cabin including having access to the river for morning coffee and playing board games in the evening after a day of tubing. The drive to the cabin was beautiful with lots of deer sightings. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leana H. £197 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Shepherdstown-Hotels-Charming-Cabin-In-The-Woods-With-River-Access.h100779583.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) ![Hallway](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/acf14b95.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) ![Porch](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/a53cd216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Inn B&B Charles Town 9.6/10 Exceptional (437) "Excellent accommodations and breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William £101 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31170000/31169200/31169171/025c8387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/32000000/31170000/31169200/31169171/8d0fa4a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/32000000/31170000/31169200/31169171/20801489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31170000/31169200/31169171/a0453b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Campfire Ring, Convenient Location, Large Groups!! Harpers Ferry 9.6/10 Exceptional (101) "The house was beyond expectations." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eddie J. £305 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Hot-Tub.h31169171.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93370000/93366000/93365959/c51d85ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/94000000/93370000/93366000/93365959/4043bef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93370000/93366000/93365959/07f0dd44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93370000/93366000/93365959/df686a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best location! The Iron Horse @ historic 1799 Inn Harpers Ferry 9.8/10 Exceptional (11) "Perfect location, very nice accommodations! Loved the layout of the top apartment and loved the close proximity to many restaurants and trails. Would love to come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna S. £202 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-1799-Inn-Harpers-Ferry-Apt-Unbeatable-Location.h93365959.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=2025-12-11&endDate=2025-12-12®ionId=6056879&adults=2&amenities=CASINO&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_BF_PROMO_6056879) ## 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](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "The breakfast was very good. The menu had a lot of options. It came to our table nice and hot! I loved the waffle with Lemon ricotta, syrup and butter. Our waitress always knew when to fill my coffee to keep it warm! Everything was very clean and neatly set up. The waitresses were also cheerful and friendly!" [](https://expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### What are the top-rated casino hotels in Winchester? > For a casino hotel in Winchester, a suitable option is the Super 8 by Wyndham Winchester VA. > > > > This hotel offers complimentary breakfast and free Wi-Fi, along with free parking for various vehicle types, including RVs, buses, and trucks. Guests have positively commented on the friendly and kind staff. ### How much does a casino hotel in Winchester cost? > Enjoy staying in a casino hotel in Winchester, with hotels from £47 offering a wide range of amenities and casino access, subject to local legal and age restrictions. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays. ### How can I save on a casino hotel in Winchester with Expedia? > There are plenty of ways to save on a casino hotel in Winchester. Join [One Key™](https://www.expedia.co.uk/welcome-one-key), our free travel rewards programme, to unlock discounted Member Prices across a range of premium hotels. Typically, booking in advance will help you save on your hotel booking. But, if you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book casino hotel in Winchester and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. ### Can I cancel my casino hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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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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