Find hotels in Old Town Winchester, Winchester from $63

Top reasons to visit Old Town Winchester

• Historic Downtown: Explore the charming streets filled with rich history and stunning architecture.
• Outdoor Adventures: Enjoy recreational areas and scenic parks perfect for family-friendly activities.
• Live Music Events: Experience vibrant live music, including local bluegrass performances.
• Cultural Experiences: Visit historic houses and significant sites that enrich your understanding of the area.
• Diverse Accommodations: Choose from a range of lodging options, from budget motels to cozy inns.

Find great hotels near Old Town Winchester

Old Town Winchester boasts a diverse selection of accommodations, ranging from budget-friendly motels to comfortable 4-star hotels. With options catering to pet owners, business travelers, and the LGBTQIA community, you’ll find the perfect place to unwind. Explore top hotels like Wyndham Winchester and charming inns that offer a welcoming atmosphere, making your stay in this historic town both enjoyable and memorable.

• La Quinta Inn & Suites by Wyndham Winchester: Perfectly tailored for business travelers and pet lovers alike, La Quinta Inn & Suites offers a welcoming retreat just 2 miles from Old Town Winchester. The hotel's business-friendly amenities include multiple meeting rooms and a fully-equipped business center, ensuring a productive stay. Guests can enjoy the comfort of pet-friendly accommodations, with provisions for dogs and cats. This hotel combines modern conveniences with a warm atmosphere, making it an excellent choice for both work and leisure.
• Travelodge by Wyndham Winchester: A cozy and budget-friendly option, Travelodge by Wyndham Winchester is ideal for pet owners looking for a simple yet comfortable stay. Located 2 miles from Old Town Winchester, this motel provides essential amenities and a welcoming environment for you and your furry friends. With its straightforward pet policy allowing for service animals and specific pet accommodations, it offers a hassle-free experience for travelers who bring their pets along on their adventures.
• Country Inn & Suites by Radisson, Winchester, VA: A family-friendly haven located 5 miles from Old Town Winchester, Country Inn & Suites combines comfort with convenience. This 3-star hotel caters to both families and business travelers, featuring spacious rooms, a complimentary breakfast, and accessible business facilities like a 24-hour business center and conference space. Pet lovers will appreciate the thoughtful amenities for their furry companions, including food and water bowls, making it a perfect choice for a well-rounded vacation experience.

Where to stay near Old Town Winchester

Old Town Winchester invites you to explore its charming streets filled with rich history and family-friendly vibes. Discover the historic architecture of downtown Winchester, enjoy scenic parks, and experience the warmth of friendly locals. Whether you're wandering through the old town or venturing into nearby neighborhoods, you'll find a delightful mix of adventure and relaxation. Embrace the unique atmosphere that makes Old Town Winchester a perfect destination for your vacation!

• Winchester: Nestled in the picturesque Shenandoah Valley, Winchester is a charming city that serves as the heart of the region. Old Town Winchester, with its historic architecture and vibrant atmosphere, draws visitors year-round, peaking in the summer and fall. Outdoor enthusiasts will appreciate the nearby recreational areas, perfect for hiking and exploring, as well as winter sports at local ski resorts. Key attractions include the scenic national parks and serene lakes, offering breathtaking views and plenty of opportunities for adventure.
• Winchester Historic District: A mere 0.2 miles from Old Town Winchester, the Winchester Historic District is a delightful neighborhood that showcases the city's rich history and culture. The area sees steady visitor traffic, especially during the warmer months and fall. Families and outdoor lovers flock here for golf courses and shopping centers, making it a lively spot for leisure and recreation. Local landmarks, such as the nearby caves and parks, offer fascinating explorations, ensuring a memorable experience immersed in the region's heritage.
• College Park: Located 2 miles from Old Town Winchester, College Park is a quaint village that attracts visitors seeking outdoor adventures and natural beauty. The area's visitor numbers remain consistent throughout the year, peaking during the summer and autumn months. College Park is ideal for those interested in recreational activities and educational experiences, thanks to its proximity to local universities and recreational areas. The village is also close to national parks and marinas, making it a great base for exploring the stunning landscapes of Virginia.

Things to do in and around Old Town Winchester

Old Town Winchester is a delightful destination for outdoor and family adventures, featuring a variety of activities such as exploring recreational areas, engaging in educational experiences, and shopping at local centers. Visitors can enjoy live music events showcasing genres like bluegrass, including fifths and progressive styles, while taking leisurely walks through the picturesque streets of the town. It's a vibrant place where fun and culture come together for an unforgettable experience.

Shopping

In Old Town Winchester, you'll discover charming shops and boutiques. Nalls Farm Market is just 1 mile away, offering fresh produce. Apple Valley Square Shopping Center, also 1 mile away, features various stores. For a larger selection, Apple Blossom Mall is 2 miles away, perfect for family shopping and entertainment.

Recreation

Experience tranquility at Jim Barnett Park, where you can enjoy serene walking trails and peaceful picnic spots just 0.9 miles away. For outdoor sports, head to Rock Harbor Golf Course, located 2 miles away, and embrace the fresh air while playing a round of golf.

For holistic wellness, visit Appleland Sports Center, 6 miles away, offering fitness classes and relaxation amenities in a welcoming environment.

Adventure

Experience the thrill of racing at Summit Point Motorsports Park, located 11 miles from Old Town Winchester, where adrenaline meets speed. For a family-friendly outdoor adventure, visit Watermelon Park Campground, 13 miles away, offering a perfect setting for camping and relaxation. Don’t miss the scenic hikes at Tuckers Lane Trailhead, 20 miles distant.

Nightlife

In Old Town Winchester, Bright Box Theater offers a vibrant cultural experience with live performances. For a thrilling night, head to Hollywood Casino at Charles Town Races, where romance and excitement blend. Alternatively, the Morgan County Observatory provides a unique family-friendly night under the stars.

Booking tips and Expedia advantages for Old Town Winchester

To save money on your trip to Old Town Winchester, consider visiting between January and March for lower accommodation rates, particularly on Tuesdays, which are the least expensive days to stay. Utilize Expedia’s search tool to find budget-friendly hotels, and consider bundling your hotel, flights, and activities for additional savings. Joining Expedia's One Key membership can also provide exclusive discounts and allow you to earn OneKeyCash for future bookings. Additionally, explore free activities in the area and take advantage of public transport for affordable travel options.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Old Town 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 around Old Town Winchester is Tuesday. The most expensive day to stay around Old Town Winchester is Saturday.
• Find cheap hotels on Expedia: Expedia’s search tool empowers you to choose your budget, desired location, and additional preferences. You can easily organize your results to display hotels from the least expensive to the most expensive, ensuring you find the best deals right away. Additionally, you have the option to narrow down your choices by hotel type; for instance, by selecting our "Eco-certified" filter, you'll discover sustainable and environmentally-friendly hotels that are available for booking.
• Consider bundling your trip: You can save money by bundling your hotel stay in Old Town Winchester with your flights and activities by choosing 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 and around Old Town Winchester

Old Town Winchester offers a delightful blend of outdoor and family-friendly adventures, making it an ideal vacation spot. Visitors can explore historic houses, colleges, and significant places, enriching their cultural experience. Highlights include the charming historic downtown, which showcases Winchester's rich heritage. Whether you're planning a trip or simply looking to enjoy the area's attractions, Old Town Winchester promises an engaging experience for all types of travelers.

• Shenandoah University: Located 1 mile away from Old Town Winchester, this historic university offers a vibrant cultural atmosphere, with beautiful architecture and landscaped grounds. It's a great place for a leisurely stroll and to appreciate the blend of history and education.
• Museum of the Shenandoah Valley: Just 0.8 mile from Old Town, this art museum features stunning exhibits that celebrate the region's rich cultural heritage, including art, history, and gardens, providing a unique glimpse into local life and creativity.
• Shenandoah Valley Discovery Museum: Situated in Old Town Winchester, this children's museum is perfect for families, offering interactive exhibits that inspire learning and exploration, making it a fun and engaging experience for all ages.

Best time to go to Old Town Winchester

Visitor numbers around Old Town Winchester is generally unchanged in popularity throughout the year. The best time to visit Old Town Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Old Town Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Old Town Winchester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.3°F (-0.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	34.7°F (1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	52.9°F (11.6°C)	Light Rain	Mostly Sunny	Average	Average
May	62.4°F (16.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	70.9°F (21.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	66.9°F (19.4°C)	Light Rain	Mostly Sunny	Average	Average
October	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
November	43.5°F (6.4°C)	Light Rain	Mostly Sunny	Average	Average
December	36.7°F (2.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average

The nearest major airports for your trip to Old Town Winchester

When planning your visit to Old Town Winchester, you have several airport options. Washington Dulles International Airport (IAD) is 42 miles away and offers nearby hotels like Hyatt Regency Dulles, Washington Dulles Airport Marriott, and Hilton Washington Dulles Airport, all providing easy access to the airport. Eastern West Virginia Regional Airport (MRB) is only 18 miles away, with accommodations such as Hillbrook Inn and Home2 Suites by Hilton Martinsburg nearby. Hagerstown Regional Airport (HGR) is 43 miles from Winchester, with options like The Mercersburg Inn and Country Inn & Suites by Radisson. Each airport offers convenient hotel options to enhance your travel experience.