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, (642 reviews)
"Rooms were so dirty sheets "
United States
Pamela
The price is €64
includes taxes & fees
24 May - 25 May
Super 8 by Wyndham Winchester VA

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
Front Royal
The price is €438
includes taxes & fees
28 May - 29 May
4BR Golf Retreat • 3 Courses • Pool Table

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (35 reviews)
"A very spacious and well equipped home to get away from it all; but, also convenient to Winchester for a night out. The fenced in areas for dogs were lovely."
United States
David A.
The price is €612
includes taxes & fees
7 Jun - 8 Jun
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,013 reviews)
"Very friendly staff....new owners Restaurant has great food"
United States
Brian
The price is €97
includes taxes & fees
14 Jun - 15 Jun
Clarion Inn Harpers Ferry - Charles Town

Hampton Inn Martinsburg

Hampton Inn Martinsburg
2.5 star property
Martinsburg
8.8 out of 10, Excellent, (1,000 reviews)
"Clean hotel, breakfast was nice, fresh. Would definitely stay again."
United States
ryan
The price is €98
includes taxes & fees
14 Jun - 15 Jun
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, (1,012 reviews)
"Clean room with a bonus jacuzzi tub. Breakfast was fresh and wonderful. Staff was super friendly. Price was great! Beds were very comfortable as well. "
United States
mary
The price is €74
includes taxes & fees
7 Jun - 8 Jun
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, (75 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is €121
includes taxes & fees
3 Jun - 4 Jun
❤️ Secluded 1940s Romantic Tiny House on the River

Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (44 reviews)
"Loved the place and area."
United States
Steve R.
The price is €293
includes taxes & fees
25 May - 26 May
Charming Cabin in the Woods with River Access

Mountain Cabin in the Woods, Near Wineries & More!

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (30 reviews)
"Nice place. "
United States
Patrick A.
The price is €210
includes taxes & fees
25 May - 26 May
Mountain Cabin in the Woods, Near Wineries & More!

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (109 reviews)
"Laura was extremely helpful as we sorted out what we needed. Amazing location near Harpers Ferry and tons of fun stuff to do right there within shouting distance of the property."
United States
Steve Y.
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
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 77 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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