Upperville Vacations from $230
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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.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Save 100% on your flight
Price was $463, price is now $230 per person
$230
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,010 reviews)
So much fun! Great Location! lots of thing to do ! The drinks at the restaurant oh boy!
Reviewed on Oct 13, 2025
Park Hyatt Washington
Northwest
Price was $3,193, price is now $725 per person
$725
per person
Dec 5 - Dec 8
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (876 reviews)
Staff at the front desk greeted me warmly. When I shared that it was my first time staying at the hotel (and I visit Washington DC about 12 times a year), I received an automatic upgrade! Free Peleton in the room allowed me to workout in the morning before a full day of meeting. the coffee in the room was SUPERB! Can't tell you how relaxing it is to have a cup of fresh brewed decaf - so delicious - before rest! I can't wait to bring my husband!
Reviewed on Sep 28, 2025
SIXTY DC
Downtown Washington D.C.
Save 100% on your flight
Price was $901, price is now $441 per person
$441
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.8/10 Exceptional! (55 reviews)
I would give this property five stars, except for the extremely poor water pressure in the shower. It also did not get very hot. The staff and all the other amenities were excellent!
Reviewed on Oct 15, 2025
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Save 100% on your flight
Price was $722, price is now $430 per person
$430
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,044 reviews)
The happy hour is fantastic, and the location is excellent. The staff is friendly, especially the overnight valet.specially the overnight valet.
Reviewed on Oct 14, 2025
Upperville Hotel Deals
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,189 reviews)
"Great hotel"
Reviewed on Oct 15, 2025
Hilton Garden Inn Dulles North
22400 Flagstaff Plaza, Ashburn, VA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $98 total per night from Nov 2 to Nov 3
$98 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Call ahead for airport shuttle .. far from anything fun !"
Reviewed on Oct 12, 2025
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Oct 26 to Oct 27
$129 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
"Great stay! Would definitely would stay again!"
Reviewed on Oct 10, 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.
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.
