Round Hill Vacations
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Find the Best Round Hill Vacation Packages
Round Hill Hotel Deals
Lansdowne Resort and Spa
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
₩287,406
₩385,286 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"The hotel property and staff were great. The service at the clubhouse restaurant was terrible. We didn’t get one of our meals until after everyone ese was already finished and had to ask to have it removed from the bill. Otherwise the hotel was lovely but the dining experience was sub par."
Reviewed on Aug 18, 2026
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
₩1,005,289
₩1,223,620 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (411 reviews)
"A really luxe resort. Outside pool area super good fun and great for kids and adults alike with separate areas. Well staffed in all areas of the hotel"
Reviewed on Aug 18, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
₩111,870
₩126,749 total
Sep 17 - Sep 18
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Very clean and lovely. We enjoyed it"
Reviewed on Aug 20, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Round Hill attractions
Stoneleigh Golf and Country Club
Nestled against the Blue Ridge Mountains, this 18-hole course features historic stone walls and a manor house. Members enjoy uncrowded fairways with strategic elevation changes and scenic natural features.
Bogati Bodega & Winery
Experience the bold flavors of Argentina in Virginia's wine country at Bogati Bodega & Winery. Savor handcrafted wines on their Buenos Aires-inspired terrace while overlooking the serene pond.
Franklin Park
This 203-acre regional park offers rolling hills, trails, and Blue Ridge Mountain views for outdoor enthusiasts. Enjoy catch-and-release fishing or attend a performance at the on-site arts center after a peaceful hike.
Round Hill Arts Center
This vibrant community arts center offers classes in oil painting, pottery and more in a welcoming atmosphere. Explore your creativity through hands-on workshops led by local artists in their fully equipped studios.
Williams Gap Vineyard
Savor award-winning wines amidst the Blue Ridge Mountains at this 200-acre estate vineyard. Relax on the outdoor terrace with a flight of estate-grown varietals while drinking in panoramic mountain views.
B-Chord Brewery
This former farm brewery at the Blue Ridge Mountain foothills combined craft beer with live music performances. Visitors enjoyed outdoor spaces while sampling local brews and listening to bands on the full-size stage.
Hill High Country Store
This marketplace celebrates Virginia's harvest with fresh local produce and legendary homemade pies. Browse artisanal crafts and organic goods while savoring the rustic charm of Loudoun County's agricultural heritage.
Round Hill Town Park
Round Hill Town Park is just one of the places to see in Round Hill, so why not enjoy the other things to explore during your travels? Take in the art scene while you're in the area.
Frequently asked questions
How much does a Round Hill vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Round Hill costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Round Hill?
Plan your getaway for the off-peak season and you're likely to score cheap Round Hill vacation packages. Remember that school vacation periods and major local events can impact prices, so do your research before booking.
How many days is enough for Round Hill?
With a well-organized itinerary, you can easily visit the most popular Round Hill attractions in a few days. But if you'd like to discover hidden spots or go on day trips, consider booking your Round Hill vacation for longer.
Is it worth booking a vacation package to Round Hill?
It's no wonder a Round Hill vacation is on the to-do list of many travelers. Top attractions like Round Hill Arts Center are just the start of things to see and do here.
How to find the best Round Hill package deals?
Start your search for a Round Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Round Hill package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Round Hill getaway off to a flying start.
Is it cheaper to book a Round Hill vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Round Hill vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Round Hill?
If you're planning a spontaneous Round Hill trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Round Hill?
- Choose when to travel: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Round Hill.
- Budget wisely: On top of the cost of your accommodations, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Round Hill.
- Decide how long to go away for: Now that you're up to speed on Round Hill, you can work out the right length of your vacation. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the right Round Hill vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
