Upperville Vacations from $187

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was $465, price is now $187 per person
$187
per person
Apr 8 - Apr 12
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,178 reviews)
I thought there would have been a coffee maker in the room lots of noise from workers working nearby betting on the wall with hammer woke me up around 8:00 am not happy. Staff was great room was very clean

Reviewed on Jan 20, 2026

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $1,133, price is now $689 per person
$689
per person
Apr 15 - Apr 20
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
I love this hotel. I always stay here when I’m in town. The staff is always so nice and pleasant. Rooms are always clean and the location is perfect and close to everything.

Reviewed on Jan 19, 2026

Hotel AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $656, price is now $402 per person
$402
per person
Mar 30 - Apr 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,205 reviews)
very clean rooms are big was a very nice hotel

Reviewed on Jan 12, 2026

Washington Hilton

Washington Hilton

4 out of 5
Northwest
Save 100% on your flight
Price was $583, price is now $377 per person
$377
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,002 reviews)
Bed so comfortable, room was comfortable, and staff super helpful.

Reviewed on Jan 19, 2026

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $485, price is now $325 per person
$325
per person
Mar 28 - Mar 30
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,786 reviews)
Clean room, quiet. Very good location.

Reviewed on Jan 15, 2026

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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
$206 nightly
The price is $235 total per night from Feb 1 to Feb 2
$235 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Clean room

Reviewed on Jan 18, 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
$641 nightly
The price is $730 total per night from Jan 25 to Jan 26
$730 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (377 reviews)
Room was awesome, amazing experiences at the resort and really great customer service

Reviewed on Jan 18, 2026

Salamander Resort And Spa
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
$92 nightly
The price is $104 total per night from Feb 15 to Feb 16
$104 total
Feb 15 - Feb 16
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Issue checking in as I had sent a note a few days in advance saying we would be checking in late, past midnight but they closed out our room prior to us arriving and we had to wait while they reactivated it :(

Reviewed on Jan 12, 2026

Hilton Garden Inn Dulles North
See all 724 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 $187 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.