Hotels in Old Town Winchester

Uncover the Timeless Charms and Hidden Treasures of Old Town Winchester

Nestled in the heart of Winchester, Virginia, Old Town Winchester is a charming blend of history and vibrant culture. Stroll along the picturesque streets lined with beautifully preserved historic buildings that echo tales from the time of George Washington. Discover local boutiques, delightful eateries, and the fascinating Shenandoah Valley Museum, where the past comes alive. Immerse yourself in the bucolic charm of this quaint destination, perfect for romantic getaways or cultural explorations. With its rich heritage and inviting atmosphere, Old Town Winchester promises an enchanting experience for every traveler. For the best hotel rates in Old Town Winchester, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Where to stay in Old Town Winchester

Old Town Winchester offers diverse attractions for travelers. The Apple Blossom Mall features shopping and dining, ideal for casual visits. Bright Box Theater hosts engaging performances, perfect for culture enthusiasts. Summit Point Motorsports Park is great for adrenaline seekers with racing events. For accommodations, you’ll find options ranging from comfortable inns to suites, with varying rates and amenities. For first-time visitors, Old Town Winchester is best, as it showcases the area’s historic charm and vibrant atmosphere. These are some of the hotels preferred by our travelers in Old Town Winchester:

1. Near Apple Blossom MallOpens in a new window: This area is perfect for families and business travelers, offering a variety of entertainment options and convenient access to shopping. The hotels here cater to different needs, with Fairfield Inn & Suites by Marriott WinchesterOpens in a new window being a 2.5-star hotel suitable for business-focused guests, featuring multiple meeting rooms and a 24-hour business center. Holiday Inn Winchester Se-Historic Gateway, an IHG HotelOpens in a new window, a 3.0-star hotel, provides amenities for both families and business travelers, including conference space and free cribs for young children. For pet lovers, Clarion Inn & Conference CenterOpens in a new window allows pets on the premises and offers business facilities, making it a great choice for those traveling with furry companions.
2. Near Bright Box TheaterOpens in a new window: This location is ideal for those looking to immerse themselves in culture and entertainment, with a romantic atmosphere perfect for couples. The Country Inn of Berkeley SpringsOpens in a new window, a 3.5-star hotel, features a full-service spa and pool, providing a relaxing retreat after a day of exploring. Maria's Garden and InnOpens in a new window, a 3.0-star bed and breakfast, offers a unique experience with golf and spa services while welcoming pets, making it a versatile choice for various travelers.
3. Near Summit Point Motorsports ParkOpens in a new window: This area is a haven for adventure seekers and sports enthusiasts, with plenty of outdoor activities available. Stone Manor Boutique InnOpens in a new window, a 3.5-star bed and breakfast, provides an adventurous experience with activities like hiking and rafting nearby, while also welcoming pets. The Hillside HotelOpens in a new window is a 2.5-star motel focusing on business travelers, offering essential facilities. Loudoun Valley ManorOpens in a new window, another 3.0-star bed and breakfast, appeals to those interested in winery experiences and also caters to business needs, making it a well-rounded option for diverse travelers.

What to do in Old Town Winchester

Three days in Old Town Winchester is ideal for immersing yourself in its rich history and vibrant culture. Enjoy leisurely walking tours, discover unique shopping destinations, savor local wines, and experience live music. Don't miss the chance to explore historic buildings and the nearby beautiful Shenandoah Valley. Here's a quick itinerary to make the most of your trip to Old Town Winchester:

• Day 1: Start your adventure at the Museum of the Shenandoah Valley, where you can explore the rich history and art of the region. After soaking in the exhibits, take a short stroll to Stonewall Jackson's Headquarters, a historical site that offers insights into the life of the famous Confederate general. Conclude your day at Frederick Douglass Park, a serene spot perfect for a leisurely walk or a picnic while reflecting on the day’s experiences.
• Day 2: Begin at the Patsy Cline Historic House, where you’ll learn about the life of the legendary country singer and her roots in Winchester. Next, head to the Kernstown Battlefield to delve into Civil War history with guided tours and educational displays. Finish your day at Abram's Delight, a historic home that showcases colonial life in the Shenandoah Valley, complete with beautiful gardens and engaging exhibits.
• Day 3: Kick off the day at Mackintosh Fruit Farm, where you can enjoy seasonal fruit picking and picturesque views of the countryside. Then, travel to Lake Serene for a relaxing afternoon by the water—ideal for a leisurely walk or a family picnic. Wrap up your trip with a visit to Red Bud Run, a beautiful natural area perfect for hiking and enjoying the scenic surroundings, making for a memorable end to your Winchester experience.

5 tips to find a great Old Town Winchester hotel deal

1. Book for the cheapest times: The most affordable time to visit Old Town Winchester is during January, November, and December when hotel prices drop significantly. For travelers on a budget, staying for at least 2-3 days is recommended to fully discover the area’s main attractions, which include a beautiful park, a national state park, and a scenic lake. This trip offers great value for money, allowing visitors to enjoy the charm of Old Town Winchester without breaking the bank.
2. Look for last-minute deals on Hotels.com: If you're looking for a spontaneous getaway to Old Town Winchester, last-minute deals can offer great savings on accommodations. To uncover these offers on Hotels.com, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, where you might find reduced rates for nearby hotels as your travel date approaches. Additionally, consider enabling email alerts or push notifications from Hotels.com to keep informed about flash sales and exclusive last-minute promotions, helping you seize any chances to save on your stay.
3. Be flexible with dates: Hotel prices can fluctuate depending on factors like the location, star rating, and the time of year. As a result, being flexible with your travel dates may help you save on hotel expenses in Old Town Winchester.
4. Consider your location: When booking on Hotels.com for your holiday, take your location into account. Staying closer to major attractions or city centers can offer convenience, but it usually tends to come with a higher price tag. If you're looking to save on costs, consider hotels in less central areas or neighborhoods, as they are more likely to be affordable while still providing reasonable access to the sights you plan to visit.
5. Upgrade with One Key: Join Hotels.com's free One Key program and book your next stay in Old Town Winchester. As a member, you can earn and use rewards points for hotel bookings. Progress through Blue, Silver, Gold and Platinum tiers to unlock various benefits like room upgrades when available, special discounts, and exclusive deals for members. Sign up today.

What to eat in Old Town Winchester

Here are some top-rated dishes in Old Town Winchester, Winchester, Virginia, United States of America:

• Apple Pie: A quintessential American dessert, this classic dish features a flaky, buttery crust filled with sweet, spiced apples. Often served warm with a scoop of vanilla ice cream, it embodies the comfort and charm of Old Town Winchester, reflecting the region's agricultural heritage.
• Barbecue: Southern barbecue in Winchester is a must-try, showcasing slow-cooked meats infused with rich, smoky flavors. Local restaurants often personalize the experience with house-made sauces and sides, inviting diners to create their own perfect plate. Enjoying barbecue here often becomes a communal affair, perfect for sharing with friends and family amidst the town’s historic backdrop.

Best time to go to Old Town Winchester

Old Town Winchester experiences its lowest average temperature in January, at 31.3°F (-0.4°C), while July is the hottest month, with an average temperature of 75.9°F (24.4°C). May is usually the wettest month. June, July, and October are the peak travel months in Old Town Winchester, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, January, February, and November tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.