Upperville Vacations from $290

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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.
Staybridge Suites Tysons - McLean by IHG

Staybridge Suites Tysons - McLean by IHG

3 out of 5
Price was $382, price is now $290 per person
$290
per person
Feb 24 - Feb 26
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
9.2/10 Wonderful! (1,000 reviews)
Just small cases can improve your room quality For example providing a better iron board or choosing a better TV set.

Reviewed on Dec 3, 2025

Hampton Inn & Suites Washington-Dulles International Airport

Hampton Inn & Suites Washington-Dulles International Airport

2.5 out of 5
Price was $426, price is now $327 per person
$327
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,001 reviews)
Very nice and clean. Good food at breakfast too. Just wish they had the fireplace working. It was cold.

Reviewed on Dec 14, 2025

Hotel Belvoir Springfield

Hotel Belvoir Springfield

3.5 out of 5
Price was $445, price is now $351 per person
$351
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,001 reviews)
The room was clean, comfortable, and i had an excellent view.

Reviewed on Dec 17, 2025

The Watermark Hotel

The Watermark Hotel

4 out of 5
Save 100% on your flight
Price was $970, price is now $772 per person
$772
per person
Jan 18 - Jan 24
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.6/10 Exceptional! (2,476 reviews)
Front Desk Staff was extremely helpful and went out of there way to welcome me

Reviewed on Dec 15, 2025

Falls Church Marriott Fairview Park

Falls Church Marriott Fairview Park

4 out of 5
Price was $647, price is now $533 per person
$533
per person
Mar 13 - Mar 18
found 16 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,001 reviews)
Great hotel but would love for yall to add an indoor pool that would make the hotel a super hit

Reviewed on Dec 14, 2025

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Upperville Hotel Deals

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza Ashburn VA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $100 total per night from Dec 28 to Dec 29
$100 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Good house keeping

Reviewed on Dec 12, 2025

Hilton Garden Inn Dulles North
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $231 total per night from Jan 1 to Jan 2
$231 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
We’ve stayed there multiple times over the years and it seems better than ever. So well kept. We live locally so

Reviewed on Dec 14, 2025

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
$586 nightly
The price is $668 total per night from Jan 7 to Jan 8
$668 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9.2/10 Wonderful! (371 reviews)
.

Reviewed on Dec 7, 2025

Salamander Resort And Spa
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 $290 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.