Upperville Vacations

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Your Upperville Vacation

When you choose a Upperville vacation package, you can relax and enjoy your getaway to the fullest. Uncover the sights and sounds of this fascinating city knowing that everything has been taken care of in advance. During your trip to Upperville, take all the time you need for sightseeing. A fantastic place to begin is Sky Meadows State Park. Expedia is here to help you escape the everyday. Tailor your vacation to Upperville to match your travel style, whatever that may be.

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
$265 nightly
The price is $302 total per night from May 25 to May 26
$302 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Always a great stay!

Reviewed on Apr 26, 2026

Lansdowne Resort and Spa
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
$596 nightly
The price is $679 total per night from May 10 to May 11
$679 total
May 10 - May 11
Total with taxes and fees
9.2/10 Wonderful! (393 reviews)
Spa was good, restaurants are good and food too, amenities are nice, air conditioning in the room was very loud all night long, woke me up several times, staff at the pool were not properly trained, we were asked to spell tequila and Chardonnay several times.

Reviewed on Apr 25, 2026

Salamander Resort And Spa
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $84 total per night from May 31 to Jun 1
$84 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (1,021 reviews)
We got in late, and the person at the front desk was a DREAM, even getting us a rollaway bed and making sure we had everything we needed. We will definitely stay there again!

Reviewed on May 5, 2026

Spark by Hilton Winchester
See all 729 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.

Find the Best Upperville Vacation Packages

Upperville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Barrel Oak Winery, The Boxwood Winery and Philip Carter Winery

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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?
You can typically find lower prices and greater availability in February, November and December. Take a look at our cheap Upperville vacation packages and you could score some great off-season deals.
How many days is enough for Upperville?
Generally, a handful of days is enough to check out the main attractions during your Upperville vacation. However, if you want to have time to rest or take day tours, consider extending your trip.
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.
Does Expedia offer Book Now, Pay Later Upperville vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Upperville break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.