Title: Book the Best Winchester CASINO Hotels & Resorts in 2025 | 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://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Casino Hotels in Winchester, VA from CA $88 ![](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 Casino Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-18&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-18&endDate=2025-10-19&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/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) ![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 drapes, 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) ![Desk, blackout drapes, 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 (612) "Kind professionals" CA $81 CA $88 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/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) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/75fa7cd1.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn Harpers Ferry - Charles Town Harpers Ferry 8.0/10 Very good (1021) "A good, clean, comfortable stay " CA $130 CA $145 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/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) ![Desk, iron/ironing board, free cribs/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) ![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) ### Hampton Inn Martinsburg Martinsburg 8.6/10 Excellent (932) "Good breakfast, great helpful staff" CA $137 CA $155 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/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) ![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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/56958e5c.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) ### Rodeway Inn & Suites - Charles Town, WV Charles Town 8.6/10 Excellent (1010) "It is a very good place to stay " CA $98 CA $111 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/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) ![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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0.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) ### ❤️ Secluded 1940s Romantic Tiny House on the River Shepherdstown 10/10 Exceptional (61) "We truly loved this location and definitely will be back!" CA $62 CA $154 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/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) ![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) ![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) ![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) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (499) "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." CA $160 CA $194 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.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) ![Interior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/07522565.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) "Host communicated well. Great location right on the river. Family had a great time. " CA $176 CA $425 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Charles-Town-Hotels-The-River-House.h114349198.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) ![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) CA $176 CA $509 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.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) ![Porch](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/a53cd216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Mary Rutherford Room](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 (431) "Excellent accommodations and breakfast. " CA $215 CA $244 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.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) ![Dining](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/00037a88.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 (37) "Very quiet and cozy property. Well maintained and nice location." CA $176 CA $358 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Shepherdstown-Hotels-Charming-Cabin-In-The-Woods-With-River-Access.h100779583.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=2025-10-31&endDate=2025-11-01®ionId=6056879&adults=2&amenities=CASINO&sort=RECOMMENDED&openPlayBack=true) ## 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 "Very nice hotel " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### Searching for casino hotels in Winchester? > If you're planning a gaming trip to Winchester, you can roll the dice at Hollywood Casino at Charles Town Races, located 18.5 mi (29.8 km) away, though 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 lodging options close to the casinos in Winchester. ### When should I take my casino trip to Winchester? > You might spend a lot of your vacation inside, but if you want to see more of the area, looking at local weather trends is a good idea. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches. ### 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, theaters, and entertainment venues, and you can check out 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 arrange a flight to the nearest airport, which is Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city center. 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[Cottages in Shawnee Land](https://www.expedia.ca/Shawnee-Land-Cottages.d553248635975849755-aaCottages.Travel-Guide-Accommodation) - [Hotels near Shenandoah University](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [Hotels near State Arboretum of Virginia](https://www.expedia.ca/State-Arboretum-Of-Virginia-Hotels.0-l6164038-0.Travel-Guide-Filter-Hotels) - [B&B in Stephens City](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Couples-Resorts-Hotels.0-0-d12076-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Pet-Friendly-Hotel.0-0-d12076-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Stephens City Hotels](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels) - [Hotels near Valerie Hill Winery](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in White Post](https://www.expedia.ca/White-Post-Hotels-Honeymoon-Hotels.0-0-d184119-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [White Post Hotels](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights to Millwood](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Gore](https://www.expedia.ca/lp/flights/3000460015/flights-from-gore) - [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [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) - [Visit Millwood](https://www.expedia.ca/Millwood.dx3000460156) - [Book Casino Hotels in Winchester on Expedia.com](https://www.expedia.com/Winchester-Hotels-Casino-Hotel.0-0-d6056879-tCasinoHotel.Travel-Guide-Filter-Hotels)