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Where to stay in Winchester

Find the best Winchester areas for the activities you enjoy most.

Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

Winchester Historic District

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

Stay near popular Winchester attractions

Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre.

Top Winchester Hotel Reviews

More cheap stays in Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Stunning Natural Landscapes: Winchester is surrounded by picturesque lakes and scenic beauty, perfect for outdoor adventures.
  • Rich Historical Significance: Explore historic houses and significant sites that showcase the area's cultural heritage.
  • Family-Friendly Attractions: Enjoy a variety of entertainment options, including an amusement park and the Alamo Drafthouse.
  • Diverse Accommodation: Choose from a range of welcoming hotels and charming agritourism properties tailored for all travellers.
  • Convenient Location: Winchester serves as an ideal base for discovering the captivating surroundings of Virginia.

Find great hotels in and around Winchester

Discover a variety of accommodation options in Winchester, Virginia, tailored to suit every traveller's needs. From the elegant Wyndham Grand and historic Wyndham hotels to charming agritourism properties, you’ll find a welcoming atmosphere for business or leisure. Enjoy an array of abundant and accessible amenities, along with pet-friendly options, ensuring a comfortable stay for all guests. Winchester’s hospitality embraces diversity, promising an inviting experience for everyone, including LGBTQIA visitors.

  • Quality Inn Winchester: Quality Inn Winchester is a welcoming hotel that caters to both families and pet lovers alike, making it an ideal choice for your vacation. With a focus on family-friendly amenities, the hotel offers complimentary cribs for younger guests, ensuring a comfortable stay for families with children. The pet policy allows dogs and cats, providing a home-like atmosphere for your furry companions. Situated conveniently within Winchester, this hotel provides easy access to local attractions while ensuring a relaxing retreat with all the necessary amenities.
  • Twi-Lite Inn: Located 27.4km from Winchester, Twi-Lite Inn offers a classic motel experience with a touch of modern entertainment. Guests can unwind in well-appointed rooms equipped with flat-screen televisions, premium TV channels, and cable TV, ensuring plenty of viewing options during your stay. The motel's emphasis on comfort and convenience makes it a suitable choice for those looking for a straightforward lodging experience with easy access to nearby attractions and amenities.
  • Travelodge by Wyndham Winchester: Travelodge by Wyndham Winchester is another excellent option for travellers seeking a pet-friendly stay. With a welcoming atmosphere, the property allows pets with certain restrictions, ensuring that your furry friends are accommodated. The hotel features essential amenities to make your stay comfortable and enjoyable, with a focus on providing a hassle-free experience. Situated conveniently within Winchester, this motel allows you to explore local attractions while returning to a relaxing environment at the end of the day.

Where to stay in and around Winchester

Winchester, Virginia, offers an enchanting blend of history and natural beauty, making it an ideal destination for outdoor enthusiasts and culture seekers alike. Explore its charming urban vibe, with family-friendly attractions and scenic landscapes just a short drive away. With easy access to interstates and nearby nature, Winchester serves as a perfect base for discovering the allure of Virginia's picturesque surroundings and alternative destinations that capture the essence of American heritage.

  • Old Town Winchester: Nestled in the heart of Winchester, Old Town Winchester is a charming neighbourhood that beckons visitors with its quaint streets and rich history. The area is particularly lively during the summer months and autumn, making it an ideal spot for those seeking outdoor adventures and scenic experiences. Visitors can enjoy a variety of activities, from shopping in local boutiques to exploring the nearby national parks. The picturesque landscape is complemented by landmarks such as the historic visitor centre, ensuring a delightful travel experience.
  • Stephenson: Located a mere 8.0km from Winchester, Stephenson is a vibrant city that offers a unique blend of culture and outdoor activities. This destination is a family-friendly haven, attracting visitors year-round, especially during the warmer months and autumn. Guests can partake in various recreational activities and immerse themselves in the local culture, with notable landmarks including historic civic buildings that tell the story of the region. The city's motor racing events are particularly popular, providing thrilling experiences for adventure seekers.
  • Gainesboro: A quaint village situated within the Winchester area, Gainesboro is a perfect retreat for families and outdoor enthusiasts alike. With its peak visitor numbers during the summer and autumn, the village offers a range of activities from skiing to exploring its stunning parks and lakes. The natural beauty surrounding Gainesboro, including impressive caves, makes it an ideal location for those looking to connect with nature. This charming village promises a memorable experience for all who visit.

Things to do in and around Winchester

Winchester, Virginia, offers an array of outdoor and adventurous activities, making it an ideal destination for nature enthusiasts. Visitors can explore its recreational areas, enjoy educational attractions, and even partake in skiing. Notable highlights include an amusement park and the Alamo Drafthouse, which provide entertainment for all ages. With its scenic beauty and engaging activities, Winchester promises a delightful holiday experience for tourists.

Shopping

In Winchester, explore the Apple Blossom Mall for a vibrant shopping experience with a mix of business and entertainment. Nalls Farm Market offers local produce, while Winchester Gateway provides a family-friendly atmosphere. If you're up for a drive, consider visiting nearby shops for more options.

Recreation

At Rock Harbor Golf Course, enjoy a round of golf amidst scenic landscapes, perfect for outdoor enthusiasts. Jim Barnett Park offers tranquil walking trails and serene picnic spots, ideal for relaxation. Just six miles away, Appleland Sports Center provides a range of wellness activities to rejuvenate your spirit.

Adventure

At Summit Point Motorsports Park, 17.7km from Winchester, thrill-seekers can experience the adrenaline rush of motor racing. North Mountain Paintball, also 17.7km away, offers exhilarating paintball battles amidst a vibrant adventure atmosphere. For a family-friendly outdoor experience, Watermelon Park Campground, located 20.9km from Winchester, is perfect for camping and exploration.

Nightlife

In Winchester, the Bright Box Theater and Winchester Little Theater offer a delightful blend of romance and culture, perfect for an enchanting evening. For a unique experience, head to the Morgan County Observatory, just 33.8km away, where you can enjoy family-friendly entertainment under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

Winchester, Virginia, offers a variety of budget-friendly activities and transport options for tourists. Enjoy free entry to sites like Shenandoah University and Mackintosh Fruit Farm. To save on accommodation, consider visiting between January and March, with Tuesdays being the cheapest nights to stay. For transport, walking, biking, or driving are good options. Use Expedia's search wizard to find the best deals by filtering for your budget and preferences, and consider package deals that combine flights and hotels for additional savings.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are January to March, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search wizard to refine your preferences, such as your budget, preferred location, and the type of hotel you desire. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.

Find the best attractions in Winchester

Winchester is an ideal destination for those seeking outdoor adventures and scenic beauty. The area boasts popular attractions such as historic houses, picturesque lakes, and significant historic sites. Visitors can enjoy a blend of culture and family-friendly experiences as they explore the rich heritage and natural surroundings of Winchester and its vicinity.

  • Shenandoah University: Experience the vibrant atmosphere of this historic institution, where education meets rich cultural traditions. Explore its beautiful campus, showcasing both modern and historical architecture, and immerse yourself in the local academic and artistic community.
  • Museum of the Shenandoah Valley: This art museum offers a unique blend of regional history and contemporary art. Wander through its galleries featuring local artists and enjoy the stunning gardens, making it a perfect spot for culture enthusiasts.
  • Shenandoah Valley Discovery Museum: A delightful children’s museum designed to inspire curiosity and learning. With interactive exhibits and hands-on activities, it's a fantastic family destination that fosters creativity and exploration for visitors of all ages.

Best time to go to Winchester

The best time to visit Winchester is dependent 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February34.7°F (1.5°C)Light RainMostly SunnySlightly LowSlightly Low
March42.3°F (5.7°C)Light RainMostly SunnyAverageSlightly Low
April52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
May62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly High
June70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
July75.9°F (24.4°C)Light RainMostly SunnySlightly HighAverage
August73.8°F (23.2°C)Light RainMostly SunnySlightly HighAverage
September66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
October55.8°F (13.2°C)Light RainMostly SunnySlightly HighSlightly High
November43.5°F (6.4°C)Light RainMostly SunnyAverageAverage
December36.7°F (2.6°C)Light RainMostly SunnySlightly LowAverage

The nearest major airports for your trip to Winchester

Winchester, Virginia, is conveniently accessible via several major airports. Washington Dulles International Airport (IAD) is situated 67.6km away, with notable hotels nearby such as the 4-star Hyatt Regency Dulles, located a mile from the airport, and the Hilton Washington Dulles Airport, just 3.2km away. Eastern West Virginia Regional Airport (MRB) is only 29.0km from Winchester, with hotel options like the Quality Inn Shepherdstown, 14.5km away. Hagerstown Regional Airport (HGR) is 69.2km distant, featuring accommodations including the 4-star Mercersburg Inn, located 13.2km from the airport. Each airport offers convenient access to their respective hotels.

Frequently asked questions

Where is the best place to stay in Winchester?
SpringHill Suites by Marriott Winchester is a favourite property for Expedia customers. This hotel offers free breakfast and an indoor pool. Other top choices based on reviews include The George Washington Hotel, A Wyndham Grand Hotel and Quality Inn Winchester. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What's the best budget-friendly accommodation in Winchester?
Based on reviews, La Quinta Inn & Suites by Wyndham Winchester is a popular hotel for our travellers who want a more economical choice, and features free buffet breakfast and free Wi-Fi. Other options to stay on the cheap include Microtel Inn & Suites by Wyndham Winchester and Travelodge by Wyndham Winchester. View all budget hotels in Winchester.
What's the best family accommodation in Winchester?
Quality Inn Winchester is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families. Other good choices for your child-friendly holiday include Hampton Inn Winchester-University/Mall Area and Microtel Inn & Suites by Wyndham Winchester. Also, attractions such as Shenandoah Valley Discovery Museum and Nalls Farm Market are fun for children of all ages. Find more child-friendly accommodations in Winchester.
What's the best LGBTQ-friendly place to stay in Winchester?
La Quinta Inn & Suites by Wyndham Winchester is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. Holiday Inn Winchester Se-Historic Gateway by IHG and Microtel Inn & Suites by Wyndham Winchester are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Winchester.
What's the best dog-friendly accommodation option in Winchester?
Quality Inn Winchester is a top hotel for people travelling with their pets, and offers a restaurant and a seasonal outdoor pool for its human guests. Other good choices for you and your pet include Hampton Inn Winchester N/Conference Center, VA and Hampton Inn Winchester-University/Mall Area. See more pet-friendly hotel accommodations in Winchester.
What are some hotels with pools in Winchester?
La Quinta Inn & Suites by Wyndham Winchester is a top hotel with an indoor pool, free buffet breakfast and free WiFi. Other choices that offer an on-site pool include Microtel Inn & Suites by Wyndham Winchester and Courtyard by Marriott Winchester. View all hotels with pools in Winchester.
What is the best spa hotel in Winchester?
The George Washington Hotel, A Wyndham Grand Hotel is a top spa hotel featuring a 24-hour fitness centre, a bar and an indoor pool. Spend an afternoon at the spa where you'll find massage treatments. In-room massages are also available. See all spa hotels in Winchester.
How is it to stay in Winchester?
Families will find child-friendly activities in Winchester, and visitors give high marks for the shopping and top-notch restaurants. Scenic and urban, this city attracts tourists with its theatres and entertainment. In Winchester, there are 76 hotels and other accommodation options to choose from. Find out more about Winchester.
What is there to see in Winchester?
Cultural venues include Bright Box Theater, Museum of the Shenandoah Valley and Winchester Little Theater. Families come for attractions such as Shenandoah Valley Discovery Museum, Nalls Farm Market and Rocking S Ranch. Notable for its historic sites, landmarks like Patsy Cline Historic House, Mt Hebron Cemetery and Stonewall Jackson's Headquarters are not to be missed. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
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.