Hotels in Old Town Winchester

Whispers of History and Nature: Unveiling the Timeless Allure of Old Town Winchester

Discover the charm of Old Town Winchester, Virginia, where history whispers through cobblestone streets and vibrant storefronts. This historic downtown area invites you to stroll along the picturesque walking mall, lined with boutiques, cafes, and galleries. Explore key attractions like the iconic Handley Library and the 18th-century Old Court House, which tell the stories of a bygone era. Enjoy local flavors at quaint eateries and immerse yourself in the rich culture that defines this captivating destination. Whether you're a history buff or a leisurely wanderer, Old Town Winchester is a delightful escape for all. For our best hotel rates in Old Town Winchester and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Old Town Winchester

Old Town Winchester offers a variety of hotel accommodations, from historic inns to modern establishments. Guests can enjoy cozy stays with charming atmospheres and easy access to local attractions. Prices vary, making it suitable for different budgets, whether you're seeking a quaint B&B or a comfortable hotel experience. Here are some of the best hotels in Old Town Winchester that our travelers love:

1. DoubleTree by Hilton Front Royal Blue Ridge ShadowsOpens in a new window: DoubleTree by Hilton Front Royal Blue Ridge Shadows is a stylish 4.0-star hotel, ideal for leisure travelers seeking a comfortable getaway. This property features a range of amenities, including a 24-hour business center, conference space, and meeting rooms, catering to those who appreciate seamless travel experiences. Guests praise the cleanliness and comfort of the rooms, along with the inviting atmosphere that makes for a delightful stay. With its convenient location and attention to detail, DoubleTree by Hilton Front Royal Blue Ridge Shadows is a captivating choice for those looking to unwind in style.
2. Hillbrook InnOpens in a new window: Hillbrook Inn, a charming 4.0-star bed and breakfast, offers a unique experience for travelers seeking a cozy retreat. With its pet-friendly policy and delightful accommodations, this hotel stands out for its inviting atmosphere and personal touches. Guests rave about the enchanting ambiance and the opportunity to explore the surrounding area. The attention to detail and warmth of the property make Hillbrook Inn an exceptional choice for those looking to create memorable moments during their stay.
3. L'Auberge Provencale Inn & RestaurantOpens in a new window: L'Auberge Provencale Inn & Restaurant is a luxurious 4.0-star hotel tailored for adventure seekers and leisure travelers. This property features excellent amenities, including a meeting room and nearby options for exhilarating activities such as hiking, rock climbing, and kayaking. Guests appreciate the stunning grounds, the serene atmosphere, and the exquisite hospitality that makes their stay truly special. With its elegant design and remarkable service, L'Auberge Provencale Inn & Restaurant provides an exceptional experience for those looking to indulge in both relaxation and adventure.

Top locations to stay in Old Town Winchester

Staying near the Shenandoah Valley Discovery Museum, Patsy Cline Historic House, and Museum of the Shenandoah Valley enhances your experience in Old Town Winchester, Virginia. The museum offers engaging exhibits for all ages, the Patsy Cline Historic House celebrates the legendary singer's legacy, and the Museum of the Shenandoah Valley showcases regional art and history. For first-time visitors, the Museum of the Shenandoah Valley is the best choice to stay near.

1. Near Shenandoah Valley Discovery MuseumOpens in a new window: Staying close to the Shenandoah Valley Discovery Museum means you're in the heart of family-friendly fun and interactive learning. This engaging spot is perfect for kids and adults alike, with hands-on exhibits that explore the region's history and culture. Plus, you're just a short stroll from charming parks and local shops, making it easy to enjoy a relaxing day in the area.
2. Near Patsy Cline Historic HouseOpens in a new window: Choosing to stay near the Patsy Cline Historic House allows you to immerse yourself in the rich musical history of one of country music's legends. The house offers a glimpse into Cline's life and career, and nearby cultural attractions like the Bright Box Theater provide a wonderful opportunity to catch a show. Don't forget to wander through the nearby shops for unique finds and local treasures.
3. Near Museum of the Shenandoah ValleyOpens in a new window: When you stay near the Museum of the Shenandoah Valley, you’ll have access to a beautiful blend of art, history, and nature. The museum features stunning gardens and exhibitions that showcase the area's heritage. You can also explore nearby points of interest like Dinosaur Land for a fun twist on local attractions, making your visit both educational and entertaining.

Things to do in Old Town Winchester

Old Town Winchester invites you to stroll through its charming streets, where boutique shopping and lively music create a vibrant atmosphere. Enjoy guided tours that reveal the area's rich history, or simply relax at outdoor cafes. With its blend of culture and community, it’s a delightful place to explore.

• Museum of the Shenandoah ValleyOpens in a new window – Discover the rich heritage of the Shenandoah Valley through art, artifacts, and beautifully landscaped gardens. Dive into local history with engaging exhibits that celebrate the region’s past, from its Native American roots to its role in the Civil War.
• Patsy Cline Historic HouseOpens in a new window – Step into the world of country music legend Patsy Cline at her childhood home. Explore the rooms filled with memorabilia and personal items, and learn about her journey from a small-town girl to an iconic star in the music industry.
• Stonewall Jackson's HeadquartersOpens in a new window – Visit the former headquarters of General Stonewall Jackson during the Civil War. Walk through the well-preserved historic site, where you can see artifacts and learn about the strategies that shaped significant battles.
• Abram's DelightOpens in a new window – Explore one of the oldest homes in Winchester, dating back to the 18th century. This charming house showcases colonial life through period furnishings and exhibits that reflect the daily lives of early American settlers.
• Old Court House Civil War MuseumOpens in a new window – Journey back to the Civil War era at this historic courthouse, which now serves as a museum. Discover intriguing exhibits that delve into local military history, and don’t miss the chance to see artifacts from this pivotal time in American history.

5 tips for savvy savings when booking a hotel in Old Town Winchester

1. Book for the cheapest times: The most budget-friendly time to visit Old Town Winchester is from January to March when hotel prices tend to be lower. For a great value for money experience, consider staying for at least 1 to 2 days to fully explore the area's key historical and cultural landmarks. During your visit, you can enjoy attractions such as the historic college university, the beautiful state park, and serene lake views, all of which offer a glimpse into the region's rich heritage. If you're on a budget, this timing could be perfect, as prices may drop even further, making your trip even more affordable.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals for Old Town Winchester, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted hotel rates as your travel date approaches. By enabling email alerts or push notifications, you could stay informed about flash sales and special promotions, helping you seize savings opportunities. Additionally, the Smart ShoppingOpens in a new window tool available via the app allows you to compare hotel prices and amenities, ensuring you're more likely to spot the best options. With real-time updates on price drops and availability, booking a last-minute getaway has never been easier.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates might help you save on your stay at a hotel in Old Town Winchester. If you're interested in unique accommodations, boutique hotels often provide a more personalized experience and could offer better value. When you book through Hotels.com, we'll inform you whether the price for your chosen dates is above or below the average. If the price is on the higher side, we’ll suggest alternative dates that may be more affordable to help you get the best deal.
4. Consider your location: Staying close to major attractions or city centers can be convenient, but it often comes with higher prices. For more budget-friendly options, you might want to look at hotels in less central areas or neighborhoods, where you can find a balance between cost and accessibility to the sites you want to visit. Additionally, considering independent hotels located a bit further out can offer a more authentic and usually more affordable experience.
5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Old Town Winchester. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

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 tends to be the wettest month. The peak travel months to visit Old Town Winchester are July, August, and October, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, January, February, and December are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny conditions.