Search Cheap Flights to
Upperville

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Upperville Flights as Low as $71

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Wed, Apr 15 - Wed, Apr 29
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$71 Roundtrip, found 5 hours ago
$71
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Apr 29, priced at $71 found 5 hours ago
Frontier Airlines
Fri, Apr 24 - Mon, Apr 27
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$82 Roundtrip, found 5 hours ago
$82
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Apr 24 from Orlando Intl. to Washington Dulles Intl., returning Mon, Apr 27, priced at $82 found 5 hours ago
Breeze Airways
Fri, Mar 27 - Mon, Apr 6
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$121 Roundtrip, found 3 days ago
$121
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Mar 27 from Orlando Intl. to Washington Dulles Intl., returning Mon, Apr 6, priced at $121 found 3 days ago
JetBlue Airways
Thu, May 14 - Tue, Jun 2
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$144 Roundtrip, found 5 days ago
$144
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, May 14 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Jun 2, priced at $144 found 5 days ago
Frontier Airlines
Wed, Apr 22 - Sat, May 9
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$180 Roundtrip, found 23 hours ago
$180
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, May 9, priced at $180 found 23 hours ago
Delta
Wed, Apr 22 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$181 Roundtrip, found 18 hours ago
$181
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, May 12, priced at $181 found 18 hours ago
American Airlines
Wed, Apr 22 - Sat, May 9
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$189 Roundtrip, found 23 hours ago
$189
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, May 9, priced at $189 found 23 hours ago
Bargain Flight
Wed, Apr 15 - Sun, Apr 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$192 Roundtrip, found 16 hours ago
$192
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Wed, Apr 15 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sun, Apr 26, priced at $192 found 16 hours ago
Frontier Airlines
Mon, Jun 1 - Tue, Jun 2
STL
Lambert-St. Louis Intl.
IAD
Washington Dulles Intl.
$197 Roundtrip, found 20 hours ago
$197
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Mon, Jun 1 from Lambert-St. Louis Intl. to Washington Dulles Intl., returning Tue, Jun 2, priced at $197 found 20 hours ago
Alaska Airlines
Wed, Apr 22 - Fri, May 1
SEA
Seattle - Tacoma Intl.
IAD
Washington Dulles Intl.
$199 Roundtrip, found 15 hours ago
$199
Roundtrip
found 15 hours ago
Select Alaska Airlines flight, departing Wed, Apr 22 from Seattle - Tacoma Intl. to Washington Dulles Intl., returning Fri, May 1, priced at $199 found 15 hours ago
American Airlines
Thu, Apr 23 - Sat, Apr 25
SEA
Seattle - Tacoma Intl.
DCA
Ronald Reagan Washington National
$232 Roundtrip, found 15 hours ago
$232
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Apr 23 from Seattle - Tacoma Intl. to Ronald Reagan Washington National, returning Sat, Apr 25, priced at $232 found 15 hours ago
Frontier Airlines
Thu, Apr 16 - Sun, Apr 19
STL
Lambert-St. Louis Intl.
DCA
Ronald Reagan Washington National
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Lambert-St. Louis Intl. to Ronald Reagan Washington National, returning Sun, Apr 19, priced at $232 found 1 day ago
Delta
Tue, Jun 16 - Thu, Jul 2
SGF
Springfield-Branson National
IAD
Washington Dulles Intl.
$329 Roundtrip, found 21 hours ago
$329
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Jun 16 from Springfield-Branson National to Washington Dulles Intl., returning Thu, Jul 2, priced at $329 found 21 hours ago
Delta
Sat, May 16 - Wed, May 20
SGF
Springfield-Branson National
DCA
Ronald Reagan Washington National
$350 Roundtrip, found 21 hours ago
$350
Roundtrip
found 21 hours ago
Select Delta flight, departing Sat, May 16 from Springfield-Branson National to Ronald Reagan Washington National, returning Wed, May 20, priced at $350 found 21 hours ago
Alaska Airlines
Wed, Apr 29 - Wed, May 6
PAE
Seattle Paine Field Intl. Airport
IAD
Washington Dulles Intl.
$420 Roundtrip, found 1 day ago
$420
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Apr 29 from Seattle Paine Field Intl. Airport to Washington Dulles Intl., returning Wed, May 6, priced at $420 found 1 day ago
Alaska Airlines
Wed, Apr 29 - Wed, May 13
PAE
Seattle Paine Field Intl. Airport
DCA
Ronald Reagan Washington National
$457 Roundtrip, found 3 days ago
$457
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Apr 29 from Seattle Paine Field Intl. Airport to Ronald Reagan Washington National, returning Wed, May 13, priced at $457 found 3 days ago

Cheap Flights to Upperville

Fall in love at first flight with your vacation to Upperville by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Upperville on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Upperville, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Upperville

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Upperville with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the DCA airport.

What is the cheapest month to fly to Upperville?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Upperville are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Upperville?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Upperville.

What airport is best to fly into Upperville?

When you’re planning your trip to Upperville, convenience is the name of the game. Luckily, Upperville Washington Dulles Intl. Airport is nearby so you can deplane and get going on checking off everything on your Upperville must-do list.

How much are flights to Upperville?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Upperville on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $71, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Upperville?

The trick to saving a stack of cash on your flight to Upperville? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $71 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$70

Last Minute Hotel Deals in Upperville

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
Book a stay at this golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,000 reviews)
Our stay was wonderful. The room was great and the staff were very polite and helpful

Reviewed on Mar 12, 2026

Get rates
Lansdowne Resort and Spa
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza Ashburn VA
Book a stay at this business-friendly hotel in Ashburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,000 reviews)
Good goodbye

Reviewed on Mar 16, 2026

Get rates
Hilton Garden Inn Dulles North
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Book a stay at this luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...
9.2/10 Wonderful! (385 reviews)
The spa treatments are amazing. In addition, the restaurant is excellent at making simple dish extra special. I highly recommend the avocado toast from the breakfast menu.

Reviewed on Mar 18, 2026

Get rates
Salamander Resort And Spa
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
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,000 reviews)
Very clean, nice bar/restaurant, convenient location. Excellent breakfast! Will definitely stay again when traveling 😄

Reviewed on Mar 14, 2026

Get rates
Holiday Inn Winchester Se-Historic Gateway by IHG
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,000 reviews)
Very nice and conveniently located

Reviewed on Mar 16, 2026

Get rates
The George Washington Hotel, A Wyndham Grand Hotel
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
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,269 reviews)
Nice room, friendly staff

Reviewed on Mar 17, 2026

Get rates
La Quinta Inn & Suites by Wyndham Winchester
Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

2.5 out of 5
726 E Market St Leesburg VA
Book a stay at this business-friendly hotel in Leesburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,001 reviews)
Good place to stay.

Reviewed on Mar 18, 2026

Get rates
Best Western Leesburg Hotel & Conference Center
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,005 reviews)
Yes the kitchen was a blessing

Reviewed on Mar 16, 2026

Get rates
Sleep Inn & Suites Winchester near University
See all 720 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.