Hotels in Upperville

Nestled in Virginia's picturesque Piedmont region, Upperville is a charming escape that melds historic allure with rural tranquility. Stroll through its quaint streets, where rustic farms meet elegant equestrian estates. Explore nearby attractions like the historic Antietam Battlefield and the vibrant downtown of Leesburg. Nature lovers can relish the rolling hills and scenic landscapes, while those seeking a romantic getaway will find cozy inns and serene wineries. Upperville invites travelers to indulge in the simple beauty of countryside living, making it an enchanting destination for both adventure seekers and history buffs alike. For the best hotel rates in Upperville, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Where to stay in Upperville

Some of the best places to stay in Upperville are Old Town Winchester, Ashburn and Harpers Ferry. Upperville, Virginia, offers a charming escape with nearby destinations like Old Town Winchester, Ashburn, and Harpers Ferry. Old Town Winchester features historic sites and vibrant shops, making it ideal for first-time visitors. Ashburn showcases modern amenities and convenience, while Harpers Ferry combines scenic beauty with rich history. Accommodations range from cozy inns to comfortable hotels, ensuring options for all travelers. Whether you prefer a quaint bed and breakfast or a suite, each area provides a welcoming stay. Here are some of the most popular hotels with our guests in Upperville:

1. Old Town WinchesterOpens in a new window: Old Town Winchester offers a charming blend of history and culture, making it a delightful destination for travelers. With attractions like Shenandoah University and the Museum of the Shenandoah Valley, visitors can immerse themselves in local art and history. For accommodations, L'Auberge Provencale Inn & RestaurantOpens in a new window is a 4.0-star hotel ideal for adventure seekers and business travelers, featuring amenities such as meeting rooms and adventure sports nearby. Hillbrook InnOpens in a new window, a 4.0-star Bed & Breakfast, caters to those traveling with pets and provides a business center and conference space. For a more luxurious stay, Salamander Resort And SpaOpens in a new window is a 5.0-star resort that includes a natural hot spring and various adventure activities, perfect for relaxation and corporate needs.
2. AshburnOpens in a new window: Ashburn is a vibrant family-friendly area with plenty of shopping and entertainment options, including One Loudoun and Dulles Town Center. For travelers seeking upscale accommodations, The Ritz-Carlton, Tysons CornerOpens in a new window is a 5.0-star hotel offering a full spa and business amenities, making it suitable for both leisure and corporate guests. The LINE Hotel DCOpens in a new window, a 4.5-star hotel, welcomes pets and features unique decor, alongside essential business services. Another option is The Royal Sonesta Washington DC Dupont CircleOpens in a new window, a 4.5-star boutique hotel providing a cozy atmosphere with business facilities, perfect for those looking to explore the area while enjoying luxury.
3. Harpers FerryOpens in a new window: Harpers Ferry is a haven for outdoor enthusiasts, showcasing stunning landscapes and historical significance through attractions like Harpers Ferry National Historical Park. The area is excellent for family adventures, from hiking to fishing. Antietam Overlook FarmOpens in a new window, a 3.5-star Bed & Breakfast, offers adventure activities like horseback riding and rafting, catering to thrill-seekers. 10 Clarke Bed & BreakfastOpens in a new window is a 4.0-star hotel with complimentary breakfast options and recreational activities nearby. Lastly, Stone Manor Boutique InnOpens in a new window, also a 3.5-star Bed & Breakfast, welcomes pets and features multiple adventure activities, making it a perfect choice for families and outdoor lovers.

Three days in Upperville offers a delightful mix of equestrian charm, with its famous horse show, scenic hikes along the Appalachian Trail, and a visit to the historic Antietam Battlefield. Explore the quaint Upperville Center and take a trip to nearby Harpers Ferry for a perfect getaway. Here's a quick itinerary to make the most of your trip to Upperville:

• Day 1: Begin your adventure at Sky Meadows State Park, where you can explore miles of scenic trails and enjoy breathtaking views of the Blue Ridge Mountains. After soaking in the natural beauty, head to PEC Holding for a delightful wine tasting experience, where you can sample local wines and learn about the winemaking process. Conclude your day at Paris Barns, a charming spot perfect for unwinding with a meal or enjoying the local atmosphere.
• Day 2: Your day kicks off with a visit to the Myron Glaser Cabin Tract, a hidden gem perfect for hiking and observing wildlife in a serene setting. Next, make your way to the historic Burwell-Morgan Mill, where you can delve into the area's rich history and witness traditional milling techniques. Wrap up your day with a relaxing time at Lake Arnold, where you can enjoy a peaceful afternoon by the water, perhaps with a picnic or some birdwatching.
• Day 3: Start your morning at Great Country Farms, a fantastic spot where you can pick fresh fruits and enjoy family-friendly activities. Then, head over to Blue Ridge Regional Park for a leisurely walk or a chance to partake in outdoor sports, all while admiring the stunning landscapes. Finish your trip at the Lewis Tracts, where you can reflect on your journey and take in the tranquil surroundings one last time, creating lasting memories of Upperville.

5 tips to find a great Upperville hotel deal

1. Book for the cheapest times: If you're looking for an affordable getaway, the best time to visit Upperville is during January, November, and December, when hotel rates are at their lowest. To make the most of your trip and truly soak in the beauty of the area, plan to stay for at least 2-3 days. During your budget-friendly stay, you can explore notable attractions such as the national park, beautiful lakes, and scenic rivers, all offering great value for money.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute deals to Upperville, you might find great options on Hotels.com. Check the DealsOpens in a new window or Last-Minute DealsOpens in a new window section for potentially discounted rates on hotels as your travel date approaches. You could discover a variety of choices with good availability, including refundable options. To stay informed about flash sales and special last-minute promotions, consider enabling email alerts or push notifications from Hotels.com, so you’re more likely to catch any opportunities to save on your getaway.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like location, star rating, and the time of year. As a result, being flexible with your travel dates could help you find better rates on hotels in Upperville.
4. Consider your location: When booking your stay 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. For more affordable options, consider looking for hotels in less central areas or neighborhoods, striking a balance between cost and easy access to the places you plan to explore.
5. Upgrade with One Key: Become a member of Hotels.com's free One Key rewards program when booking your stay in Upperville. Earn points for your hotel bookings and progress through Blue, Silver, Gold and Platinum tiers. Unlock a range of exclusive rewards, including room upgrades when available, discounted rates, and member-only offers. Join today.

Best time to go to Upperville

Upperville experiences its lowest average temperature in January, at 31.8°F (-0.1°C), while July is the hottest month, with an average temperature of 76.5°F (24.7°C). September is typically the wettest month. If you’re looking to soak up the lively atmosphere in Upperville, April to June are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by light rainfall. However, if you prefer a more relaxed experience, January, October, and December are perfect for a quieter getaway, marked by light rainfall and mostly sunny conditions.