Upperville Vacations from $416
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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.
Embassy Suites by Hilton Washington D.C. – Convention Center
Downtown Washington D.C.
Save 100% on your flight
Price was $987, price is now $605 per person
$605
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (2,031 reviews)
Staff was kind, rooms were clean, breakfast was decent. My only 2 complaints, which are not biggies, are that the beds are not comfortable and that i didnt like being harrassed daily to buy a vacation package for hilton. I would however stay here again.
Reviewed on Dec 1, 2025
Salamander Washington DC
Southwest
Save 100% on your flight
Price was $642, price is now $441 per person
$441
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Washington (DCA)
9.4/10 Exceptional! (1,021 reviews)
We had an amazing experience to stay with family. Thank you for your great service.
Reviewed on Dec 1, 2025
The Churchill Hotel near Embassy Row
Northwest
Save 100% on your flight
Price was $885, price is now $609 per person
$609
per person
Jan 15 - Jan 22
found 1 hour ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
we arrived at the Hotel early morning and pretty much aware that check in time is not until 3pm, the receptionist gave us a mean look on why are we checking in early, and there’s a $50 fee if we do she said, which is not a problem for us since we are exhausted and tired, after we paid, her demeanor completely changed. The room was very stuffy and has a funny smell so we opened the window to get rid of the smell, the bed and pillows are very comfortable, clean and warm, the bathroom is on a small side and no place to hang your towels, the staff needs to be more welcoming and friendly. We asked for our complimentary wine on the first day and the reception staff keep telling us that it will be delivered to our room, nothing was delivered until our 3rd day my husband finally went to the front desk and ask once again , the lady at the desk reach out underneath and hand us the bottle without saying anything 😩😹 construction noise is very annoying too. Won’t be coming back ☹️☹️☹️
Reviewed on Dec 1, 2025
The Graham Georgetown
Georgetown
Save 100% on your flight
Price was $754, price is now $530 per person
$530
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip flight included
Miami (MIA) to Washington (DCA)
8.8/10 Excellent! (1,786 reviews)
This is a very nice, clean, and conveniently located hotel in the heart of Georgetown. Very comfortable bed and nicely decorated room.
Reviewed on Nov 30, 2025
Upperville Hotel Deals
Lansdowne Resort and Spa
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! (1,009 reviews)
Yes
Reviewed on Dec 1, 2025
Hilton Garden Inn Dulles North
22400 Flagstaff Plaza Ashburn VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $79 total per night from Jan 4 to Jan 5
$79 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
yes
Reviewed on Dec 1, 2025
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
$585 nightly
The price is $666 total per night from Dec 16 to Dec 17
$666 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (370 reviews)
It’s a great hotel. However, they don’t have non-Tesla EV chargers, nor adapters for other cars. That’s already odd, given this is a fancy hotel next to DC. But it’s even odder that they don’t tell you that there’s a (paid) EV charger in the parking lot of the Town Hall, *literally* next door to ...
Reviewed on Dec 1, 2025
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
