Find hotels in Old Town Winchester, Winchester

Top reasons to visit Old Town Winchester

• Historic Walking Tours: Explore Old Town Winchester’s rich history through guided walking tours, showcasing key historic sites.
• Charming Shopping Experience: Discover unique local shops and boutiques in the scenic Old Town walking mall.
• Family-Friendly Outdoor Activities: Enjoy recreational areas and scenic lakes, perfect for family adventures.
• Cultural Immersion: Visit nearby museums that highlight the town’s heritage and cultural significance.
• Diverse Accommodation Options: Choose from historic hotels to modern stays, catering to various traveler preferences.

Find great hotels near Old Town Winchester

Old Town Winchester offers a charming selection of accommodations, perfect for any traveler. Whether you're seeking a historic hotel or a modern stay, you'll find options that cater to pet-friendly, business-minded, and LGBTQIA-friendly experiences. Notable choices include the Wyndham Winchester and various agritourism properties, all conveniently located near the vibrant heart of Old Town. Enjoy a memorable vacation in this picturesque area, rich in history and hospitality.

• Travelodge by Wyndham Winchester: A convenient motel option for travelers seeking a pet-friendly stay, Travelodge by Wyndham Winchester is located 2 miles from Old Town Winchester. This property is ideal for those who want to enjoy their vacation with their furry companions, as it allows pets with certain restrictions. The welcoming atmosphere and essential amenities ensure a comfortable stay, making it a great choice for families and casual travelers alike. Guests appreciate the straightforward accommodations and the ease of access to nearby attractions.
• La Quinta Inn & Suites by Wyndham Winchester: Offering a blend of comfort and professional amenities, La Quinta Inn & Suites by Wyndham Winchester caters to both leisure and business travelers. Located 2 miles from Old Town Winchester, this hotel is LGBTQIA welcoming and pet-friendly, making it a versatile choice for diverse guests. The property features a well-equipped business center and multiple meeting rooms, ideal for corporate stays. Guests enjoy spacious rooms and a complimentary breakfast, along with the convenience of bringing their pets along for the adventure.
• Red Roof Inn Winchester, VA: A family-friendly hotel that embraces both comfort and inclusivity, Red Roof Inn Winchester, VA is positioned 2 miles from Old Town Winchester. This LGBTQIA welcoming property is perfect for travelers with children, offering amenities such as free cribs and a welcoming environment for families. Additionally, it allows pets, making it easy for guests to travel with their beloved animals. With its convenient location and accommodating services, this hotel ensures a pleasant and enjoyable stay for all its visitors.

Where to stay near Old Town Winchester

Old Town Winchester offers a charming blend of history and modernity, perfect for outdoor and family adventures. Stroll through its scenic streets, where local shops and friendly faces abound. With a great location, you can explore nearby attractions within walking distance, immersing yourself in the rich historical atmosphere. Whether you're seeking family-friendly activities or a taste of urban life, Old Town Winchester is a delightful destination for every traveler.

• Winchester: Nestled in the heart of the Shenandoah Valley, Winchester is a vibrant city that offers a delightful mix of outdoor adventures and historical charm. Visitors flock here year-round, with peak arrivals during the summer and autumn months. The city is surrounded by stunning landscapes, making it an ideal spot for hiking and exploring national parks. Popular activities include skiing and enjoying scenic vistas at local lakes. Winchester’s recreational areas invite families and adventure-seekers alike to immerse themselves in nature while experiencing the rich culture and history of the region.
• Winchester Historic District: Just a short 0.2-mile stroll from Old Town Winchester, the Historic District is a treasure trove of charming architecture and family-friendly activities. The area is known for its welcoming atmosphere, where visitors can enjoy golf courses and shopping centers while soaking in the rich history that surrounds them. Peak travel times coincide with the summer and fall, making it a popular destination for families and outdoor enthusiasts. With easy access to parks and visitor centers, the Historic District offers an engaging experience that balances leisure and adventure.
• College Park: Located 2 miles from Old Town Winchester, College Park is a quaint village that beckons outdoor enthusiasts and adventure seekers. The village is characterized by its picturesque landscapes and recreational areas, perfect for skiing during the winter months. Visitors can enjoy the proximity to national parks and marinas, providing ample opportunities for exploration and relaxation. The steady flow of travelers throughout the year, peaking in summer and fall, reflects its appeal as a scenic getaway that offers a blend of tranquility and adventure.

Things to do in and around Old Town Winchester

Old Town Winchester offers a delightful blend of outdoor adventures and family-friendly activities. Visitors can enjoy walking tours that highlight historic sites, explore the local shopping center, and take advantage of recreational areas. For an enriching experience, check out educational tours that delve into the area's rich history. Whether you're strolling through charming streets or planning a travel itinerary, Old Town Winchester has something for everyone.

Shopping

In Old Town Winchester, visit Nalls Farm Market for fresh produce and unique gifts, just a mile away. Apple Valley Square Shopping Center and Eastgate Plaza Shopping Center, also a mile away, offer a variety of shops and a family-friendly atmosphere, perfect for finding souvenirs.

Recreation

Jim Barnett Park offers a peaceful retreat with walking trails, picnic areas, and beautiful gardens, perfect for relaxation. The Rock Harbor Golf Course invites you to enjoy the outdoors with its scenic fairways and challenging holes. For indoor activities, Appleland Sports Center provides fitness classes and wellness programs in a welcoming atmosphere.

Adventure

At Summit Point Motorsports Park, thrill-seekers can experience exhilarating motor racing, located 11 miles from Old Town Winchester. For a family-friendly adventure, Watermelon Park Campground offers outdoor fun 13 miles away. Hikers will love Tuckers Lane Trailhead, where scenic trails await 20 miles from the town.

Nightlife

Experience vibrant nightlife at Bright Box Theater for live performances and engaging shows. For a unique outing, visit the Morgan County Observatory, just 21 miles away, to marvel at the stars. Don’t miss the Winchester Little Theater nearby for captivating cultural productions and family-friendly entertainment.

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 when accommodation prices drop. Tuesdays are the cheapest days to stay, while Saturdays are the most expensive. Use Expedia to compare prices and combine hotel stays with flights for better deals. Joining the One Key membership can unlock exclusive discounts and OneKeyCash for future bookings. Don’t forget to take advantage of free activities in the area and look for special offers like free nights and beverage discounts to maximize your savings.

• 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: Utilize Expedia’s search tool to narrow down your options based on your budget, desired location, and preferred type of accommodation. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Old Town Winchester with your flights and activities through an Expedia package deal.
• 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 fun and family-friendly adventures, making it an ideal vacation spot. Visitors can explore historic houses, enjoy the scenic lakes, and immerse themselves in the rich culture of the historic downtown area. Don't miss the charming Old Town Winchester walking mall and nearby museums that showcase the town's heritage, all within the picturesque Winchester Historic District.

• Shenandoah University: Located 1 mile from Old Town Winchester, Shenandoah University offers a rich cultural atmosphere with its beautiful campus and historic architecture. Visitors can explore the vibrant arts scene, attend performances, and enjoy the engaging community.
• Museum of the Shenandoah Valley: Just 0.8 miles away, this art museum features an impressive collection of regional art and artifacts. The museum hosts various exhibitions and events that celebrate the history and culture of the Shenandoah Valley.
• Shenandoah Valley Discovery Museum: Situated within Old Town Winchester, this children's museum provides a fun and educational experience for families. With interactive exhibits that promote learning through play, it's perfect for young explorers.

Best time to go to Old Town Winchester

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	Slightly High	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	Average	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

Traveling to Old Town Winchester, Virginia, is convenient with several nearby airports. Washington Dulles International Airport (IAD) is located 42 miles away, with hotel options like Hyatt Regency Dulles and Hilton Washington Dulles Airport, both within 2 miles of the airport. Eastern West Virginia Regional Airport (MRB) is 18 miles away, with comfortable stays at Hillbrook Inn and Home2 Suites by Hilton Martinsburg, just a few miles from the terminal. Lastly, Hagerstown Regional Airport (HGR) is 43 miles from Old Town Winchester, offering accommodations like The Mercersburg Inn and Springhill Suites by Marriott Hagerstown, all within a short drive from the airport.