Upperville Vacations from $318

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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.

The Latest Upperville vacation packages

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,767 reviews)
I have stayed here before. Good value for the price. Wifi was slow and spotty

Reviewed on Jun 17, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
Hotel AKA Alexandria

Hotel AKA Alexandria

4 out of 5
Old Town North
Save 100% on your flight
per person
Sep 7 - Sep 11
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
9.4/10 Exceptional! (462 reviews)
The staff are your backbone and they do a fantastic job! We'll be back.

Reviewed on Jun 12, 2025

Apartments at the Heart of Arlington

Apartments at the Heart of Arlington

3.5 out of 5
Ballston
Save 100% on your flight
per person
Sep 7 - Sep 11
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
8.6/10 Excellent! (7 reviews)
Nice place, parking was easy to get in front of the property on the street. Supplies were very limited in the apartment. We had to rush to nearby 7-11 multiple times to get supplies for bathroom as all those were limited in the quantity and ran out in 1-2 days and we had to stay there for 4-5 days.

Reviewed on May 27, 2025

Metro-Friendly DC Apartments

Metro-Friendly DC Apartments

3 out of 5
Pentagon City
Save 100% on your flight
per person
Sep 7 - Sep 11
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
9/10 Wonderful! (2 reviews)
It was great and very close to DC for the night events and restaurants

Reviewed on May 12, 2025

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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
$262 nightly
The price is $298 total per night from Jun 30 to Jul 1
$298 total
Jun 30 - Jul 1
Total includes taxes and 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
$104 nightly
The price is $113 total per night from Jul 6 to Jul 7
$113 total
Jul 6 - Jul 7
Total includes taxes and 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
$87 nightly
The price is $94 total per night from Jun 29 to Jun 30
$94 total
Jun 29 - Jun 30
Total includes taxes and 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.

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 from $318 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.