Upperville Vacations

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    Save up to NT$25,000 when you book a flight and hotel together*

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Find the Best Upperville Vacation Packages

Upperville Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA
NT$4,140
NT$4,691 total
Oct 5 - Oct 6
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
Salamander Resort And Spa

Salamander Resort And Spa

500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
NT$23,077
NT$28,086 total
Sep 27 - Sep 28
includes taxes & fees
9.2/10 Wonderful! (420 reviews)
"They would not let my wife in the room at check in due to her not being listed as a traveler. Huge inconvenience even though she had her id and I called to tell them to let her in. Pool was open until 6 pm. Wife couldn’t get to the pool cause she wasn’t let in pool area till traveler was set up. ..."

Reviewed on 2026/9/22

Salamander Resort And Spa
Lansdowne Resort and Spa

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
NT$8,259
NT$10,729 total
Oct 27 - Oct 28
includes taxes & fees
Lansdowne Resort and Spa
See all 761 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.

Stay near popular Upperville attractions

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.
See properties

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.

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