Upperville Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Upperville Vacation Packages

Upperville 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 ￥31,545 per night from Jun 30 to Jul 1
￥31,545
￥41,342 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"They need to update the rooms ...at this price point it doesn't cut it."

Reviewed on Jun 9, 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 ￥15,036 per night from Jul 6 to Jul 7
￥15,036
￥16,360 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (2,056 reviews)
"Eh"

Reviewed on Jun 16, 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 ￥13,485 per night from Jul 6 to Jul 7
￥13,485
￥15,108 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Easy to get to very clean great service"

Reviewed on Jun 12, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 704 properties in Upperville
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 an Upperville vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. But how much your vacation to Upperville costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Upperville?
Plan your getaway for the off-season and you're likely to score cheap Upperville vacation packages. Keep in mind that school vacation periods and local festivals and events can have an impact on prices, so do your research before booking.
How many days is enough for Upperville?
Typically, a handful of days is enough to see the major attractions during your Upperville vacation. However, if you want to have time to rest or take day trips, consider extending your itinerary.
How to find the best Upperville package deals?
Begin your search for an Upperville package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Upperville package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Upperville escape off to a flying start.
Is it cheaper to book an Upperville vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Upperville vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Upperville?
If you're considering a spur-of-the-moment Upperville trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Upperville?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to visit Upperville.
  2. Budget wisely: On top of the price of your accommodations, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Upperville.
  3. Decide your trip length: Consider how much time you want to spend discovering Upperville. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Upperville vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.