Winchester Hotel Guide - Casino Hotels in Winchester, Virginia

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Top Winchester Casino Hotels

Clarion Inn Harpers Ferry - Charles Town

2.5 star property
8.0 out of 10, Very good, (1006)
"A good, clean, comfortable stay "
The price is €88
includes taxes & fees
3 Nov - 4 Nov
Clarion Inn Harpers Ferry - Charles Town

The Inn at Charles Town - Hollywood Casino

3.0 star property
8.6 out of 10, Excellent, (496)
"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."
The price is €123
includes taxes & fees
3 Nov - 4 Nov
The Inn at Charles Town - Hollywood Casino

Hampton Inn Martinsburg

2.5 star property
8.6 out of 10, Excellent, (928)
"Great hotel "
The price is €103
includes taxes & fees
21 Oct - 22 Oct
Hampton Inn Martinsburg

Super 8 by Wyndham Winchester VA

2.0 star property
6.2 out of 10, (610)
"Kind professionals"
The price is €59
includes taxes & fees
2 Nov - 3 Nov
Super 8 by Wyndham Winchester VA

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (429)
"Excellent accommodations and breakfast. "
The price is €162
includes taxes & fees
22 Oct - 23 Oct
The Carriage Inn B&B

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

10.0 out of 10, Exceptional, (5)
The price is €315
includes taxes & fees
20 Oct - 21 Oct
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
8.6 out of 10, Excellent, (1003)
"It is a very good place to stay "
The price is €70
includes taxes & fees
2 Nov - 3 Nov
Rodeway Inn & Suites - Charles Town, WV

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is €94
includes taxes & fees
19 Oct - 20 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

Charming Cabin in the Woods with River Access

9.6 out of 10, Exceptional, (34)
"Very quiet and cozy property. Well maintained and nice location."
The price is €261
includes taxes & fees
13 Oct - 14 Oct
Charming Cabin in the Woods with River Access

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (59)
"Clean comfortable fully stocked within walking distance to everything Leesburg has to offer -a GREAT place to stay ... beds were so comfy and so was the sofa definitely would stay again ... totally loved it!! "
The price is €265
includes taxes & fees
7 Oct - 8 Oct
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

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

Explore a world of travel with Expedia

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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 79 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 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 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.