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Top Winchester hotels

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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.

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Studio in the Heart of the Shenandoah Valley

Studio in the Heart of the Shenandoah Valley

Mount Jackson
2/10 (1 review)
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.

Seize your some day

Winchester Hotel & Travel Guide

If you're checking out modern lodgings in Winchester, you'll have no shortage of choices. Right now, Travelocity compares 21 places to stay within a 6-mile (10-kilometer) distance of Winchester's center.

The The George Washington Hotel, A Wyndham Grand Hotel is a much-desired hotel choice thanks to the fact that it is located such a convenient distance from central Winchester.

Stephens City is a district that is where you can find 3 accommodation options, making it the area with the widest range of Winchester hotels. The Holiday Inn & Suites Front Royal Blue Ridge Shadows and Holiday Inn Express Winchester South-Stephens City are great examples of the hotel establishments in and around Stephens City.

Front Royal, Middletown and Strasburg are three alternative Winchester locales that offer excellent lodgings. In Front Royal, accommodation options include the Hampton Inn Front Royal and Cool Harbor Motel. Or, if you base yourself in Middletown, you will be able to pick from the Wayside Inn and Econo Lodge Inn & Suites. Strasburg, which is situated 17 miles (27 kilometers) from the center of town, offers the Fairfield Inn & Suites Strasburg Shenandoah Valley and Hotel Strasburg.

Those traveling on a budget will be happy to know that there is a good range of cheaper places to stay in the vicinity of Winchester. The Comfort Inn Stephens City is 8 miles (12 kilometers) from downtown, while the Ramada Strasburg Va is 16 miles (26 kilometers) away. Other budget room options include the Quality Inn Skyline Dr and the Super 8 Front Royal.

You could also try the Hillbrook Inn along with the The George Washington Hotel, A Wyndham Grand Hotel. The Hillbrook Inn is situated just 13 miles (22 kilometers) away from the city center of Winchester. The The George Washington Hotel, A Wyndham Grand Hotel, is only 0.2 miles (0.3 kilometers) away. Alternative options include the Hampton Inn - Winchester N/Convention Center and the Hilton Garden Inn Winchester.

For those wanting to check out more of the valleys and rolling hills that are a big feature in this region of the country, you should plan some extra time in Shenandoah Valley. Spend your time hiking or discover many of the district's major things to see. Comfortable Travelocity-listed rooms are located nearby.

Woodstock is 30 miles (45 kilometers) to the southwest of Winchester and is home to Woodstock Museum and Shenandoah County Fairgrounds. The Hampton Inn & Suites Woodstock and Holiday Inn Express Woodstock-Shenandoah Valley are some of the Travelocity-listed hotel and apartment options in Woodstock. 45 miles (73 kilometers) southwest of Winchester, you may also choose to stay at New Market, which features the Quality Inn Shenandoah Valley and Days Inn New Market Battlefield. The Endless Caverns and New Market Battlefield are some more popular attractions to check out while in New Market.

Washington Dulles International Airport is a primary gateway for air travel, and is found 40 miles (67 kilometers) away from Winchester's downtown. Travelocity-listed places to stay nearby are Embassy Suites Dulles Airport and Washington Dulles Airport Marriott.

Winchester hotels essential information

Accommodation
1,981 hotels
Lowest Price
$73
Highest Price
$137
Popular hotels
La Quinta Inn & Suites by Wyndham Winchester, Comfort Inn & Suites, The George Washington Hotel, A Wyndham Grand Hotel, Sleep Inn & Suites, Travelodge by Wyndham Winchester, Holiday Inn Winchester Se-Historic Gateway by IHG, Microtel Inn & Suites by Wyndham Winchester, Red Roof Inn Winchester, VA, Courtyard by Marriott Winchester

Top reasons for your vacation to Winchester

  • Charming Old Town: Explore the picturesque streets of Old Town Winchester and admire its historic architecture and quaint shops.
  • Wolvesey Castle: Visit this stunning castle, known for its beautiful gardens and rich history dating back to the 12th century.
  • Vibrant Music Scene: Immerse yourself in Winchester's local music scene by catching live performances at various venues throughout the city.
  • Kernstown Battlefield: History buffs will enjoy a visit to this Civil War battlefield, where they can learn about the area's significant role in the conflict.
  • Outdoor Adventures: Take advantage of Winchester's scenic beauty by hiking or biking along its picturesque trails, or enjoy family-friendly activities in the local parks.

Find your favorite hotels in Winchester

If you're planning an outdoor vacation in Winchester, Virginia, you'll find a range of hotel accommodations to suit your needs. From budget-friendly options to luxurious resorts, there are hotels available for every traveler. Winchester offers a variety of popular hotels that provide comfortable rooms and convenient amenities. Whether you're looking for a top hotel with all the bells and whistles or a cheap hotel that won't break the bank, you'll find the perfect place to stay in Winchester.

Hotel nameTypeStarsDescription
La Quinta Inn & Suites by Wyndham WinchesterHotel2.5This 2.5-star hotel is a great option for your outdoor vacation in Winchester. It offers close proximity to rafting, hiking, golf, and trendy attractions. With an indoor pool and fitness center, it provides accessible facilities for your family. The hotel is also pet-friendly and offers connecting rooms for convenience.
Microtel Inn & Suites by Wyndham WinchesterHotel2.5Another 2.5-star hotel, this option provides comfortable accommodation for your family's outdoor getaway.
The George Washington Hotel, A Wyndham Grand HotelHotel3.5With a 3.5-star rating, this hotel is perfect for history enthusiasts. It offers close proximity to historical sites, as well as activities like snowshoeing, walking, and snowboarding. The hotel also features a hot tub, indoor pool, and offers wedding and massage services.

Explore the best activities and sights in Winchester

Winchester, Virginia is the perfect destination for an outdoor family vacation. With its close proximity to historical landmarks, breathtaking scenery, and urban attractions, there is something for everyone to enjoy. Explore the charming streets of Old Town Winchester, visit top places like Wolvesey Castle, and immerse yourself in the local music scene at various venues. For history buffs, a visit to the Kernstown Battlefield is a must. Whether you're strolling through the town, dining at family-friendly cafes, or enjoying outdoor activities, Winchester offers a plethora of options for a memorable vacation.

  1. Shenandoah University: Shenandoah University is a historic college university that offers a unique experience with its friendly people, lively entertainment, diverse dining options, and affordable prices. Take a leisurely walk on the campus and soak in the rich history and vibrant atmosphere. Enjoy a captivating theater performance or explore the nearby historical sites and charming churches. Shenandoah University is the perfect place to immerse yourself in the local culture and engage in educational excursions.
  2. Museum of the Shenandoah Valley: The Museum of the Shenandoah Valley is an art museum that provides a delightful experience with its friendly staff, delightful dining options, and enjoyable walking trails. Discover a treasure trove of artistic masterpieces and immerse yourself in the local culture through engaging exhibits and theater performances. Take a guided tour to fully appreciate the historical significance of the museum and nearby churches. And don't forget to indulge in a cup of coffee as you admire the beauty of the valley. The Museum of the Shenandoah Valley is a must-visit for culture enthusiasts.
  3. Apple Blossom Mall: Apple Blossom Mall is a shopping mall center that offers a unique experience with its friendly atmosphere, rich historical background, and entertaining activities. Explore a wide range of stores and enjoy a delightful shopping experience. Indulge in delectable dining options or catch a thrilling hockey game at the mall. The mall also features a theater where you can watch the latest movies. Take a leisurely walk and admire the historical architecture of nearby churches. Apple Blossom Mall is the perfect destination for families and those seeking entertainment and business opportunities in the city.

Where to stay in Winchester

Winchester, Virginia is a charming city that offers a perfect blend of historical and scenic attractions for your outdoor vacation. Immerse yourself in the city's rich culture as you explore the old town, which is easily accessible on foot. Discover the beauty of Winchester's scenic parts as you hike or bike along the picturesque trails. For a family-friendly experience, visit the local parks and enjoy outdoor activities such as picnicking and playing sports. With its welcoming atmosphere and abundance of outdoor adventures, Winchester is sure to provide you and your family with a joyful and memorable vacation.

  1. Old Town Winchester: Old Town Winchester is a charming neighborhood that offers a unique blend of history, shopping, and dining. Families can explore the historic streets and buildings, taking in the rich heritage of the area. There are plenty of shops and boutiques to browse, offering a range of unique and locally made products. The neighborhood is also known for its diverse dining options, from cozy cafes to lively bars. Visitors can enjoy leisurely walks, taking in the friendly atmosphere and live music that often fills the air. With guided tours available, families can learn more about the area's fascinating past while enjoying a family-friendly and welcoming environment.

Best times to go to Winchester

Winchester has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 75.9 degrees Fahrenheit. The wettest month in Winchester is May, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January31.3°F (-0.4°C)Light RainMostly Sunny
February34.7°F (1.5°C)Light RainMostly Sunny
March42.3°F (5.7°C)Light RainMostly Sunny
April52.9°F (11.6°C)Light RainMostly Sunny
May62.4°F (16.9°C)Light RainMostly Sunny
June70.9°F (21.6°C)Light RainMostly Sunny
July75.9°F (24.4°C)Light RainMostly Sunny
August73.8°F (23.2°C)Light RainMostly Sunny
September66.9°F (19.4°C)Light RainMostly Sunny
October55.8°F (13.2°C)Light RainMostly Sunny
November43.5°F (6.4°C)Light RainMostly Sunny
December36.7°F (2.6°C)Light RainMostly Sunny

Food and dining in Winchester

When visiting Winchester, Virginia, be prepared to indulge in some delicious local cuisine. One popular option is Texas Roadhouse, a highly rated steakhouse that offers mouthwatering cuts of meat. Another great choice is Golden Corral, a highly rated restaurant known for its diverse North American dishes. And if you're in the mood for pizza, Villa Donato is a highly popular pizzeria that will satisfy your cravings. With these restaurants, you'll be able to treat your family to a variety of flavorful meals during your vacation in Winchester.

How do I find a great hotel with Travelocity?

Ensure your entire crew has a memorable vacation with our reliable and comprehensive online travel platform. Discover the perfect accommodations for families by using the family-friendly badge, which highlights hotels that offer extra amenities for kids. Our custom filters allow you to easily narrow down options to hotels nearest to top attractions, offering enhanced cleaning, and within your price range.

Why should I book with Travelocity?

Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide worry-free travel every time you and your family book with us so that you can spend less time fretting and more time creating cherished memories. With us, you'll find and create your perfect trip, along with transparent pricing and verifiable reviews, and round-the-clock guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Winchester?

When planning your trip to Winchester, Virginia, consider visiting the following affordable attractions: 1) The Museum of the Shenandoah Valley, which showcases the region's art, history, and gardens. 2) The Old Court House Civil War Museum, where you can learn about Winchester's role in the Civil War. 3) The Shenandoah Valley Discovery Museum, a hands-on children's museum with interactive exhibits. By bundling your flights, hotel, and car bookings, you can save money and have more to spend on exploring these family-friendly attractions.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Family getaways are where the best memories are made, but it’s no secret that traveling with children can be stressful. These kid-friendly Winchester hotels offer perks designed to keep adventurers of all ages comfortable and happy: Put your bags down at The George Washington Hotel, A Wyndham Grand Hotel. It comes with a swimming pool, a pillowtop mattress and a knack for making families feel welcome. Modern Upscale Home, Historic Downtown Winchester is another top pick. After an exciting day of exploring, return to your comfy room and perks like animal viewing activities and free WiFi.
Where can I find cheap hotels in Winchester?
At Travelocity you’ll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we’ve already found in Winchester then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $73. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 1,981 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during July, August and October. If you’d prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We’ve got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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