Winchester Hotel Guide - Casino Hotels in Winchester, Virginia

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Check availability on Winchester Casino Hotels

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, (626 reviews)
"Easy to book."
United States
Maria
The price is €63
includes taxes & fees
1 Mar - 2 Mar
Super 8 by Wyndham Winchester VA

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,006 reviews)
"Overall, this hotel was clean, quiet, a good option to explore Harper's Ferry. "
United States
Jessie
The price is €85
includes taxes & fees
5 Mar - 6 Mar
Clarion Inn Harpers Ferry - Charles Town

Hampton Inn Martinsburg

Hampton Inn Martinsburg
2.5 star property
Martinsburg
8.6 out of 10, Excellent, (1,013 reviews)
"Quiet area and close to food and shopping. Breakfast was great. "
Canada
Suresh
The price is €88
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn Martinsburg

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1,006 reviews)
"Staff was very courteous "
United States
Crystal
The price is €65
includes taxes & fees
22 Feb - 23 Feb
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, (71 reviews)
"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
2 Mar - 3 Mar
❤️ Secluded 1940s Romantic Tiny House on the River

Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (11 reviews)
"Great location in Lower Harper's Ferry. We completely enjoyed our stay. Will definitely be staying again in the future."
United States
Andrew R.
Best location! Baltimore Suite @ 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 reviews)
"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 €371
includes taxes & fees
24 Feb - 25 Feb
Cottage on King | Charming Historic Leesburg Home

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, (541 reviews)
"Clean room and facilities and super friendly staff"
United States
Jenn
The price is €111
includes taxes & fees
23 Mar - 24 Mar
The Inn at Charles Town - Hollywood Casino

The River House

The River House
Charles Town
10.0 out of 10, Exceptional, (14 reviews)
"Host communicated well. Great location right on the river. Family had a great time. "
United States
Geoff C.
The price is €302
includes taxes & fees
22 Feb - 23 Feb
The River House

Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (49 reviews)
"Great location!"
United States
Ellen K.
Best location! The Pullman Apt @ historic 1799 Inn
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, 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 Museum of the Shenandoah Valley and Old Court House Civil War Museum. 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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