Round Hill Vacations

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Find the Best Round Hill Vacation Packages

Round Hill Hotel Deals

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is ₩258,520 per night from Sep 1 to Sep 2
₩258,520
₩346,236 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"The property was beautiful….the people on staff were extremely friendly, and the rooms were very clean. Planning on staying here again in the Fall. 😊"

Reviewed on Aug 10, 2025

Lansdowne Resort and Spa
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is ₩143,738 per night from Sep 1 to Sep 2
₩143,738
₩156,390 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on Aug 10, 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is ₩129,156 per night from Aug 17 to Aug 18
₩129,156
₩144,696 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Staff was very helpful and accommodating. Thanks so much!"

Reviewed on Aug 9, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 797 properties in Round Hill
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.

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.