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 $101 - ![](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 [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-01&endDate=2025-11-02&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-02&endDate=2025-11-03&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Casino Hotels ![Bar (on property)](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/47d3b88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/042e58ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/ed64133f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/59b8161f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi Boyce 9.8/10 Exceptional (29) "Came for my daughters wedding and this place was amazing. Awesome place to relax, firepit to chat around, outside table to enjoy a meal was amazing, comfy beds. Just awesome and amazing stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah D. CA $411 CA $882 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Boyce-Hotels-NEW-WINE-COUNTRY-ESCAPE-Hot-Tub-Fire-Pit-Fast-Wi-Fi-Gas-Grill.h85477424.Hotel-Information) ![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 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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/917000/916960/48e1065a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Winchester VA Winchester 6.2/10 (614) "Improvements could be made with housekeeping, but a nice stay all the same" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judy CA $92 CA $101 total includes taxes & fees Nov 16 - Nov 17 [](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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/cba53522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn Harpers Ferry - Charles Town Harpers Ferry 8.0/10 Very good (1045) "Great staff. Great location. Great restaurant " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bradley CA $125 CA $140 total includes taxes & fees Nov 9 - Nov 10 [](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) ![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) ![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) ![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 (941) "Very clean and smelled great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $125 CA $141 total includes taxes & fees Nov 28 - Nov 29 [](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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/56958e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Smoking](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 (1026) "Great for the value!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tabitha CA $89 CA $101 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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/80506691.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 (63) "We truly loved this location and definitely will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Astrid CA $55 CA $147 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x60y0-c1839f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The River House Charles Town 10/10 Exceptional (9) "Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey W. CA $121 CA $358 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Charles-Town-Hotels-The-River-House.h114349198.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) ![Dining](https://images.trvl-media.com/lodging/101000000/100780000/100779600/100779583/00037a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cabin in the Woods with River Access Shepherdstown 9.6/10 Exceptional (38) "Loved the cabin and seclusion. Would come back for sure. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark S. CA $175 CA $357 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) ![Casino](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/d7ac3540.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) ![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) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (504) "Great place to stay to go to the casino" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $164 CA $198 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92540000/92539200/92539156/e3d29e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92540000/92539200/92539156/ec99cdf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92540000/92539200/92539156/c79e1dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92540000/92539200/92539156/8456a5aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best location! Baltimore Suite @ historic 1799 Inn Harpers Ferry 9.6/10 Exceptional (11) "This property is the perfect location for those staying in Harpers Ferry. The accommodations were nice, and the location made it easy to explore the historic sites and businesses in Harpers Ferry. We recommend this property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John F. CA $182 CA $309 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Harpers-Ferry-Hotels-1799-Inn-Harpers-Ferry-Apt-Unbeatable-Location.h92539156.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=2025-11-15&endDate=2025-11-16®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 "Service was great!!" [](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 78 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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[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)