Winchester Hotel Guide - Casino Hotels in Winchester, Virginia

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Our top choices for Winchester hotels with a casino

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (622)
"Very limited, bread , butter , jam"
Canada
Susan
Super 8 by Wyndham Winchester VA

Hampton Inn Martinsburg

Hampton Inn Martinsburg
2.5 star property
Martinsburg
8.6 out of 10, Excellent, (1029)
"Excellent staff and amenities for the price"
United States
Samuel
The price is €82
includes taxes & fees
18 Jan - 19 Jan
Hampton Inn Martinsburg

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1013)
"Room was clean, nice view to the nature, staff was great."
United States
Rao
The price is €85
includes taxes & fees
18 Jan - 19 Jan
Clarion Inn Harpers Ferry - Charles Town

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1004)
"Certainly will stay again "
United States
philip
The price is €61
includes taxes & fees
22 Jan - 23 Jan
Rodeway Inn & Suites Charles Town

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (68)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is €93
includes taxes & fees
12 Jan - 13 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
Charles Town
8.6 out of 10, Excellent, (531)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is €123
includes taxes & fees
12 Jan - 13 Jan
The Inn at Charles Town - Hollywood Casino

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (440)
"Excellent accommodations and breakfast. "
United States
William
The price is €197
includes taxes & fees
6 Feb - 7 Feb
The Carriage Inn B&B

Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (11)
"Great location in Lower Harper's Ferry. We completely enjoyed our stay. Will definitely be staying again in the future."
United States
Andrew R.
The price is €193
includes taxes & fees
7 Jan - 8 Jan
Best location! Baltimore Suite @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.4 out of 10, Exceptional, (48)
"Great location!"
United States
Ellen K.
The price is €175
includes taxes & fees
8 Jan - 9 Jan
Best location! The Pullman Apt @ historic 1799 Inn

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (68)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
The price is €331
includes taxes & fees
7 Jan - 8 Jan
Cottage on King | Charming Historic Leesburg Home
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.

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

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 76 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, Winchester Gateway or Apple Valley Square 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 Museum of the Shenandoah Valley and Winchester Little Theater. 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. If you'd like to explore around the area, consider renting a car to explore more sights.

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