Find hotels in Winchester, VA from $75

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Compare 1,999 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Learn more about Winchester
Old Town Winchester map

Old Town Winchester

2 out of top 10 points of interest in this area

Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

Winchester Historic District map

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester and related destinations

Come to Winchester and enjoy its history, food, and entertainment.

Find out more about Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Rich Historical Significance: Explore landmarks like the Old Court House and the Museum of the Shenandoah Valley, showcasing the area's cultural heritage.
  • Outdoor Adventures: Enjoy national and state parks, perfect for hiking, picnicking, and engaging with nature.
  • Family-Friendly Attractions: Discover various activities for families, including educational experiences related to George Washington.
  • Relaxing Hot Springs: Unwind at nearby hot springs after a day of exploration, offering a unique relaxation experience.
  • Diverse Accommodations: Choose from budget-friendly options to luxurious stays, catering to every traveler's needs.

Find great hotels in Winchester

Winchester, Virginia, offers a diverse selection of accommodations to meet every traveler's needs, from budget-friendly options to luxurious stays. Whether you're looking for a cozy bed & breakfast or a comfortable hotel, you'll find various choices, including popular chains like Wyndham and Country Inn. With amenities catering to families, business travelers, and pet owners alike, Winchester ensures a pleasant and memorable vacation experience for all visitors.

  • La Quinta Inn & Suites by Wyndham Winchester: La Quinta Inn & Suites by Wyndham Winchester caters to both business and pet-friendly travelers. This modern hotel is well-equipped with a fully accessible business center and multiple meeting rooms, making it an ideal choice for corporate guests. Pet lovers will appreciate the welcoming atmosphere, as pets are permitted with certain restrictions. Guests can enjoy amenities such as free Wi-Fi, a complimentary breakfast, and spacious rooms designed for comfort. With its strategic location in Winchester, you can easily explore local attractions while still enjoying the convenience of a business-oriented stay.
  • Travelodge by Wyndham Winchester: Travelodge by Wyndham Winchester offers a budget-friendly option with a focus on simplicity and comfort. This motel is pet-friendly, allowing for a hassle-free stay for those traveling with furry companions. While amenities are basic, you can expect clean and comfortable rooms alongside essential services. The staff is known for their warm hospitality, ensuring a pleasant experience for all guests. Whether you’re passing through or planning a longer stay, Travelodge provides a practical and accommodating choice for your visit to Winchester.
  • Microtel Inn & Suites by Wyndham Winchester: The Microtel Inn & Suites by Wyndham Winchester is designed for families, business travelers, and pet owners alike. This hotel provides a range of amenities, including free cribs for younger guests and a business center for corporate needs. Pets are welcome with certain guidelines, enhancing the family-friendly atmosphere. Guests can enjoy complimentary breakfast and high-speed Wi-Fi, along with comfortable rooms that make for a relaxing stay. Located conveniently in Winchester, this hotel ensures you have everything you need for a memorable visit.

Discover the best areas to stay in Winchester

Winchester, Virginia, is a perfect destination for those seeking outdoor adventures and scenic beauty. Explore the city’s rich history with visits to landmarks like the Old Court House and the Museum of the Shenandoah Valley. Venture into the surrounding regions, where family-friendly attractions and breathtaking landscapes await. Don’t miss the nearby hot springs for relaxation after a day of exploring. Experience the warm atmosphere and friendly locals that make Winchester a memorable vacation spot.

  • Harpers Ferry: Located 25 miles from Winchester, Harpers Ferry is a charming historical town nestled at the confluence of the Potomac and Shenandoah Rivers. This area is a haven for outdoor enthusiasts, offering breathtaking scenery and adventurous activities year-round. The town's proximity to the Harpers Ferry National Historical Park makes it a popular destination for hiking, biking, and exploring rich Civil War history. With peak visitor numbers from May to July, you can enjoy activities like skiing in the winter months or taking in the stunning views from the numerous recreational areas nearby.
  • Berkeley Springs: Situated 31 miles away from Winchester, Berkeley Springs is renowned for its natural mineral springs and relaxing spa experiences. This quaint town attracts visitors year-round, particularly in June to July and September. The area boasts beautiful parks, a golf course, and outdoor recreational opportunities that make it a perfect getaway for relaxation and adventure. Berkeley Springs State Park, with its historic bathhouse, and the tranquil lake nearby provide serene spots for unwinding amidst nature.
  • Front Royal: Just 18 miles from Winchester, Front Royal serves as the gateway to the Shenandoah National Park. This vibrant town offers an array of outdoor activities, making it a favorite among adventure seekers throughout the year. With the peak travel months in April, July, and September, visitors can enjoy skiing in the winter and hiking, picnicking, and wildlife viewing in warmer seasons. Front Royal's stunning landscapes and recreational areas make it an ideal destination for those looking to immerse themselves in nature.

Things to do in Winchester

Winchester, Virginia, offers a delightful mix of outdoor adventures and scenic beauty, making it an ideal destination for nature lovers. Explore the city's recreational areas, engage in educational experiences, and enjoy shopping at local malls. Whether you seek thrilling activities or a relaxing day in the great outdoors, Winchester has something for everyone to enjoy!

Food and drinks

Indulge in local flavors at Valerie Hill Winery, 9 miles from Winchester, offering a romantic atmosphere. For outdoor vibes, visit A-T Gift Company Farm Winery, 18 miles away. Bluemont Vineyard, 19 miles from the city, combines entertainment with a picturesque setting for a delightful experience.

Shopping

In Winchester, you can shop at the Apple Blossom Mall for a variety of stores and family-friendly vibes. For fresh produce and local goods, visit Nalls Farm Market or Shen-Val Farm Market, located 9 miles away, offering a delightful country experience.

Recreation

Play a round at Rock Harbor Golf Course, where the beautiful greens and outdoor atmosphere provide a refreshing escape. For relaxation, head to Jim Barnett Park, offering serene walking trails and peaceful spots to unwind. A short drive away, Appleland Sports Center invites you to enjoy wellness activities in a calming environment.

Adventure

Summit Point Motorsports Park offers exhilarating motor racing experiences, located 11 miles from Winchester, perfect for adrenaline junkies. For a family-friendly outdoor adventure, Watermelon Park Campground, 13 miles away, provides a relaxed atmosphere. For hiking enthusiasts, Tuckers Lane Trailhead, 20 miles away, showcases stunning scenery and nature trails.

Nightlife

Experience Winchester's vibrant nightlife at Bright Box Theater for a romantic evening of culture and entertainment. For a thrilling night, venture 19 miles to Hollywood Casino at Charles Town Races, where city vibes and excitement await. Don’t miss the charming Winchester Little Theater for more family-friendly performances.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, consider visiting free attractions like Shenandoah University, Apple Blossom Mall, and Jim Barnett Park. For transportation, walking, biking, or using a car are budget-friendly options. The best time to visit for lower prices is from November to January. Use Expedia to find affordable hotels by sorting results from lowest to highest price, and consider booking a package deal for additional savings. Joining Expedia's One Key membership can also provide exclusive discounts and help you earn rewards for future stays.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are November to January, where the prices are slightly lower. This is in comparison to April to May and September, where prices are slightly higher.
  • Find cheap hotels on Expedia: Expedia's search tool makes it easy for you to set your budget, choose your ideal location, and more. You can arrange your search results from the lowest to the highest prices, ensuring you see the most affordable hotels first. Additionally, you can refine your choices by hotel type. For instance, selecting the "Eco-certified" filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities by booking an Expedia package.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in Winchester

Winchester, Virginia, offers a delightful mix of outdoor adventures and rich history. Visitors can explore national and state parks, historic sites, and local visitor centers that provide insights into the area’s cultural heritage. Families and outdoor enthusiasts will find plenty to enjoy, including attractions related to George Washington, making it an ideal destination for those seeking a scenic and educational experience.

  • Shenandoah University: Explore the beautiful campus of this historic university, known for its vibrant cultural atmosphere. Enjoy art exhibits, music performances, and the rich history that permeates its halls.
  • Museum of the Shenandoah Valley: Delve into the region's history and art at this captivating museum. With its diverse collection of art, artifacts, and beautiful gardens, it offers a unique glimpse into the cultural heritage of the Shenandoah Valley.
  • Shenandoah Valley Discovery Museum: Perfect for families, this interactive children's museum encourages learning through play. With hands-on exhibits and engaging activities, it’s a delightful place for kids to explore and discover.

Best time to go to Winchester

Visitor numbers in Winchester is generally unchanged in popularity throughout the year. The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February34.7°F (1.5°C)Light RainMostly SunnySlightly LowAverage
March42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
April52.9°F (11.6°C)Light RainMostly SunnyAverageSlightly High
May62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly High
June70.9°F (21.6°C)Light RainMostly SunnySlightly HighAverage
July75.9°F (24.4°C)Light RainMostly SunnySlightly HighAverage
August73.8°F (23.2°C)Light RainMostly SunnyAverageAverage
September66.9°F (19.4°C)Light RainMostly SunnyAverageSlightly High
October55.8°F (13.2°C)Light RainMostly SunnySlightly HighAverage
November43.5°F (6.4°C)Light RainMostly SunnySlightly LowSlightly Low
December36.7°F (2.6°C)Light RainMostly SunnyAverageSlightly Low

The nearest major airports for your trip to Winchester

Traveling to Winchester, Virginia, can be conveniently done via several major airports. Washington Dulles International Airport (IAD) is located 42 miles away, with nearby hotel options including the 4-star Hyatt Regency Dulles and The Westin Washington Dulles Airport, both just 1 mile from the airport. Martinsburg, WV (MRB-Eastern West Virginia Regional) is only 18 miles from Winchester, with the 4-star Hillbrook Inn and the 3.5-star Carriage Inn B&B situated 11 miles from the airport. Lastly, Hagerstown Regional Airport (HGR) is 43 miles away, featuring the 4-star Mercersburg Inn and the 3-star Springhill Suites by Marriott Hagerstown within a short drive.

Frequently asked questions

What is the best area to stay in Winchester?
Old Town Winchester stands out as the best area to stay for travelers seeking a blend of history, charm, and convenience. This picturesque neighborhood is renowned for its well-preserved 18th-century buildings and vibrant Main Street, where boutique shops, inviting restaurants, and local art galleries create a delightful atmosphere. Visitors can explore the historic Old Court House and enjoy scenic walks along the lovely pedestrian mall, all while being just a short drive from the beautiful Shenandoah Valley.

For couples looking to immerse themselves in romance, Old Town Winchester offers a quaint backdrop for leisurely strolls and intimate dining experiences. The area's cozy cafes and wine bars provide superb spots to unwind and connect, while the historic ambiance adds an extra touch of magic to your getaway.

Families will appreciate the variety of activities available in this family-friendly area. With access to outdoor parks and historical sites, there are plenty of opportunities for both education and adventure. The nearby Museum of the Shenandoah Valley is a great option for engaging exhibits that entertain and educate visitors of all ages.
What are the best hotels in Winchester that travelers recommend?
The George Washington Hotel, A Wyndham Grand Hotel, stands out as a premier choice in Winchester, boasting an outstanding score of 9.4. Guests are drawn to its historic charm and modern amenities, including premium bedding that ensures a restful night's sleep. With valet parking available, you can enjoy a straightforward arrival and departure, allowing you to focus on exploring the rich history of Winchester.

For families, the Holiday Inn Winchester Se-Historic Gateway by IHG is a fantastic option, receiving a great rating of 9.0. With accessible indoor pools, it provides a superb spot for kids to splash around while parents unwind. The hotel also features designer toiletries for a touch of luxury, making it ideal for those seeking comfort without sacrificing value.

If you're looking for a contemporary and stylish stay, Spark by Hilton Winchester, also rated at 9.0, is an excellent pick. Its air-conditioned rooms promise a comfortable retreat after a day of adventures, while the attentive service ensures you feel welcomed throughout your stay.

Couples seeking a romantic getaway may find the Hilton Garden Inn Winchester particularly appealing, with a rating of 8.8. Featuring a beautiful garden-view restaurant and wedding services, it provides a serene atmosphere superb for celebrating special moments. The accessible indoor pool adds to the charm, making it easy to relax together while enjoying the hotel's amenities.

Lastly, the Courtyard by Marriott Winchester, with an 8.8 rating, is superb for those who appreciate spacious suites. Guests highlight the inviting indoor pool as a great way to unwind after a busy day of sightseeing, making it a wonderful choice for both families and couples alike.
What are the best family hotels in Winchester?
The George Washington Hotel, A Wyndham Grand Hotel is an exceptional choice for families visiting Winchester, boasting an outstanding score of 9.4. This historic hotel offers connecting rooms and complimentary cribs, making it easy to accommodate families of all sizes. Guests appreciate the attentive service and elegant decor, ensuring a comfortable and enjoyable stay.

Another fantastic option is the Holiday Inn Winchester Se-Historic Gateway by IHG, which has earned a rating of 9.0. This family-friendly hotel features a refreshing pool where kids can splash around, and it offers free stays for children. With convenient amenities like a microwave and daily housekeeping, families can enjoy a straightforward experience while exploring the area. Additionally, the hotel has a snack bar, great for grabbing a quick bite on the go.

For those looking for a more contemporary vibe, Spark by Hilton Winchester, also rated 9.0, provides a inviting space with connecting rooms and free cribs. Families can rely on daily housekeeping and the availability of microwaves for easy meal prep, ensuring a stress-free stay.

Lastly, the Courtyard by Marriott Winchester, rated 8.8, features a pool for family fun and includes options for breakfast, making it a great spot for families to start their day. With amenities like a sofa bed and a garden area for relaxation, this hotel blends comfort with convenience seamlessly.

Each of these hotels prioritizes family needs, offering a variety of amenities designed to make your stay enjoyable and stress-free. Whether you're looking for a historic charm or , Winchester has the great family-friendly lodging for you. Find more child-friendly accommodations in Winchester.
What are the best spa hotels in Winchester?
For a luxurious retreat, The George Washington Hotel, A Wyndham Grand Hotel, stands out in Winchester with an outstanding score of 9.4. This elegant hotel combines historic charm with modern amenities, ensuring a relaxing and enjoyable stay. Guests can indulge in a full-service spa that offers a range of rejuvenating treatments, including in-room massages for those who prefer to unwind in the comfort of their own space. See all spa hotels in Winchester.
What hotels in Winchester offer free breakfast?
Spark by Hilton Winchester is a fantastic choice for travelers seeking a comfortable and convenient stay in Winchester, VA. This hotel boasts a stellar review score of 9.0, ensuring that guests can expect attentive service and a friendly setting. Enjoy complimentary breakfast options, including a hearty continental spread, superb for fueling your day's adventures. For relaxation, unwind in the private hot tub after a day of exploration or take advantage of the well-equipped fitness facilities.

Another excellent option is the Country Inn & Suites by Radisson, Winchester, which has a review score of 8.6. This family-friendly hotel offers an indoor pool, making it a delightful spot for those traveling with children. Guests appreciate the complimentary buffet breakfast available on weekends, ensuring everyone starts their day off right. The property also provides free Wi-Fi in rooms, accessible fitness facilities, and convenient self-parking options. Find more hotels with free breakfast in Winchester.
What are the top pet-friendly hotels in Winchester?
The George Washington Hotel, A Wyndham Grand Hotel, is a distinguished choice for travelers seeking a blend of luxury and comfort in Winchester, VA. With a stellar review rating of 9.4, this Georgian-style property features an onsite full-service spa where you can indulge in rejuvenating treatments, along with a fitness center that operates around the clock. The hotel also offers various outdoor adventures nearby, such as mountain biking and skiing, making it superb for those looking to unwind after a day of adventure.

For families traveling with pets, the Spark by Hilton Winchester stands out with a review score of 9.0. This inviting hotel allows pets and provides a range of convenient amenities such as free breakfast, a hot tub for relaxation, and complimentary toiletries. Families will appreciate the availability of cribs at no charge, ensuring a comfortable stay for little ones.

Another excellent option for families is the Holiday Inn Winchester Se-Historic Gateway, which also carries a review rating of 9.0. This hotel features an indoor pool---superb for children to splash around---and offers free accommodations for kids. Its location in the historical district adds a cultural twist, allowing families to explore local attractions with ease.

For couples or solo travelers, the Courtyard by Marriott Winchester, rated 8.8, offers a cozy atmosphere with spacious suites and an indoor pool, ideal for a romantic getaway or a serene escape from the daily grind. The Hilton Garden Inn Winchester, also rated 8.8, caters to both pet owners and couples, providing suites and a range of amenities to make your stay comfortable and memorable.

No matter your travel purpose, Winchester offers a variety of accommodations that emphasize attentive service and quality, ensuring a stress-free planning experience for every guest. See more pet-friendly hotels in Winchester.
What are the best budget hotels in Winchester?
The Comfort Inn & Suites in Winchester is a fantastic choice for budget-conscious travelers, boasting an impressive review score of 9.4. This hotel ensures a stress-free stay with a variety of complimentary amenities, including free breakfast options served on weekends, free Wi-Fi in guest rooms, and ample self-parking. Guests appreciate the accessibility features and the convenient location near shopping districts, which makes it ideal for families looking to explore the area.

Another excellent option for families is the SpringHill Suites by Marriott Winchester, also rated 9.4 by guests. This hotel offers a family-friendly atmosphere with an indoor pool superb for the kids to splash around in, along with free cribs for younger guests. The complimentary continental breakfast is a great way to start the day on the right note, ensuring everyone is fueled for the adventures ahead.

For those seeking a touch of elegance, The George Washington Hotel, A Wyndham Grand Hotel, rated 9.2, offers a more upscale experience while still being accessible for families. With an on-site spa and fitness center, it caters to couples looking for a romantic getaway, while the nearby mountain biking and skiing options appeal to adventure seekers.

Lastly, the La Quinta Inn & Suites by Wyndham Winchester, with a review score of 9.2, features both indoor pool facilities and complimentary breakfast, making it a comfortable option for families. The friendly space and convenient amenities, such as accessible parking, cater to a wide range of travelers, ensuring everyone finds their superb fit in Winchester. View all budget hotels in Winchester.
When is the best time to go to Winchester?
The most popular time to visit Winchester is during the summer months, particularly July. This is when the city buzzes with life, offering a vibrant atmosphere filled with outdoor festivals and events. Average temperatures during this time reach the mid-70s Fahrenheit, creating inviting conditions for leisurely strolls through the historic streets or enjoying the lush greenery in the surrounding parks.

As you navigate through Winchester's attractions, you'll find that the peak season extends from July to September. This period attracts many visitors, eager to experience the charming architecture, including the magnificent Winchester Cathedral and the Great Hall. The pleasant weather encourages outdoor dining, where you can indulge in the local cuisine at cafes with lovely patio seating, adding to the city's enchanting ambiance.

For those who prefer a quieter visit with lower prices, consider planning your trip in late October or early November. While the weather may be cooler, averaging in the low 50s Fahrenheit, this time allows for a more intimate experience with the city, as you can explore its rich history and culture without the crowds. Plus, the autumn colors provide a picturesque backdrop for your adventures.
Where can I find the best nightlife in Winchester?
Winchester, Virginia, is a charming city that offers a delightful blend of history and modern amenities, making it a great destination for nightlife enthusiasts.

The Old Town area is the heart of Winchester's nightlife, featuring a variety of bars and restaurants housed in historic buildings. You can enjoy a casual evening at local favorites like the Lost Rhino Brewing Company, which offers a fantastic selection of craft beers and a relaxed atmosphere, superb for unwinding after a day of exploring.

For a more upscale experience, head to the vibrant Cork Street downtown, where you'll find a selection of wine bars and cocktail lounges. Establishments like the 1787 Brewing Company provide a lively setting with live music on weekends, making it a great spot to socialize and enjoy the local scene.

Additionally, the area around the Winchester Medical Center features a few late-night options that cater to those looking for a fun night out. Whether you prefer a quiet drink or a lively night of dancing, Winchester offers a variety of experiences to suit your mood.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Winchester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $75 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.