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Upperville

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Upperville Flights as Low as $92

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

Frontier Airlines
Thu, May 22 - Sat, May 24
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$92 Roundtrip, found 2 days ago
$92
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 22 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 24, priced at $92 found 2 days ago
Frontier Airlines
Fri, May 23 - Sat, May 24
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 23 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 24, priced at $98 found 2 days ago
Frontier Airlines
Mon, May 19 - Sat, May 24
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$106 Roundtrip, found 2 days ago
$106
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 19 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 24, priced at $106 found 2 days ago
Frontier Airlines
Mon, Jun 2 - Fri, Jun 6
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Orlando Intl. to Washington Dulles Intl., returning Fri, Jun 6, priced at $120 found 5 days ago
United
Sat, May 10 - Sat, May 10
ORD
O'Hare Intl.
IAD
Washington Dulles Intl.
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select United flight, departing Sat, May 10 from O'Hare Intl. to Washington Dulles Intl., returning Sat, May 10, priced at $164 found 6 days ago
American Airlines
Sat, May 10 - Sat, May 10
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, May 10 from O'Hare Intl. to Ronald Reagan Washington National, returning Sat, May 10, priced at $164 found 6 days ago
United
Sat, May 10 - Sat, May 10
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select United flight, departing Sat, May 10 from O'Hare Intl. to Ronald Reagan Washington National, returning Sat, May 10, priced at $164 found 6 days ago
JetBlue Airways
Fri, May 30 - Fri, May 30
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, May 30 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Fri, May 30, priced at $179 found 4 days ago
Delta
Sat, May 24 - Sun, May 25
BNA
Nashville Intl.
DCA
Ronald Reagan Washington National
$179 Roundtrip, found 13 hours ago
$179
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, May 24 from Nashville Intl. to Ronald Reagan Washington National, returning Sun, May 25, priced at $179 found 13 hours ago
United
Sun, May 25 - Sat, May 31
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$182 Roundtrip, found 5 days ago
$182
Roundtrip
found 5 days ago
Select United flight, departing Sun, May 25 from Los Angeles Intl. to Washington Dulles Intl., returning Sat, May 31, priced at $182 found 5 days ago
United
Tue, Jul 1 - Tue, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$185 Roundtrip, found 15 hours ago
$185
Roundtrip
found 15 hours ago
Select United flight, departing Tue, Jul 1 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Tue, Jul 8, priced at $185 found 15 hours ago
JetBlue Airways
Tue, Jun 3 - Fri, Jun 6
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jun 3 from Orlando Intl. to Ronald Reagan Washington National, returning Fri, Jun 6, priced at $190 found 6 days ago
Frontier Airlines
Tue, May 13 - Sat, May 17
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 13 from Los Angeles Intl. to Ronald Reagan Washington National, returning Sat, May 17, priced at $191 found 2 days ago
Hawaiian Airlines
Wed, May 7 - Fri, May 30
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Wed, May 7 from Los Angeles Intl. to Washington Dulles Intl., returning Fri, May 30, priced at $205 found 6 days ago
Alaska Airlines
Sun, May 25 - Sat, May 31
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sun, May 25 from Los Angeles Intl. to Washington Dulles Intl., returning Sat, May 31, priced at $210 found 5 days ago
United
Fri, May 23 - Sun, Jun 1
BNA
Nashville Intl.
IAD
Washington Dulles Intl.
$250 Roundtrip, found 4 days ago
$250
Roundtrip
found 4 days ago
Select United flight, departing Fri, May 23 from Nashville Intl. to Washington Dulles Intl., returning Sun, Jun 1, priced at $250 found 4 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 May, 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 16 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 $92, 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 $92 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$91

Last Minute Hotel Deals in Upperville

Lansdowne Resort and Spa
Lansdowne Resort and Spa
4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
The price is $287 per night from Apr 28 to Apr 29
$287
includes taxes & fees
Apr 28 - Apr 29
Stay at this 4-star golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.6/10 Excellent! (1,002 reviews)
"Overall a nice experience, however, I found staff at front desk, sundry shop and bar to be inattentive and unwelcoming"

Reviewed on Apr 16, 2025

Lansdowne Resort and Spa
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is $102 per night from Apr 27 to Apr 28
$102
includes taxes & fees
Apr 27 - Apr 28
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 ...
9/10 Wonderful! (1,945 reviews)
"Check in was super simple Our room was decent for the price. Needs a little maintenance in our room, but overall a good deal for your money. Saw several families with dogs that seemed please with accomodations."

Reviewed on Apr 18, 2025

La Quinta Inn & Suites by Wyndham Winchester
Salamander Resort And Spa
Salamander Resort And Spa
5 out of 5
500 North Pendleton Street, Middleburg, VA
The price is $725 per night from May 11 to May 12
$725
includes taxes & fees
May 11 - May 12
Stay at this 5-star luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Red Fox Fine Art and Museum of ...
9/10 Wonderful! (345 reviews)
"Always beautifully clean and luxurious! We wished that we had received the VIP benefit."

Reviewed on Apr 19, 2025

Salamander Resort And Spa
Clarion Inn Harpers Ferry - Charles Town
Clarion Inn Harpers Ferry - Charles Town
2.5 out of 5
4328 William L Wilson Fwy, Harpers Ferry, WV
The price is $100 per night from Apr 27 to Apr 28
$100
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Harpers Ferry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
8/10 Very Good! (1,007 reviews)
"The location was easy to find and convenient for us."

Reviewed on Apr 17, 2025

Clarion Inn Harpers Ferry - Charles Town
Hilton Garden Inn Dulles North
Hilton Garden Inn Dulles North
3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
The price is $142 per night from Apr 27 to Apr 28
$142
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star 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! (1,001 reviews)
"The place was clean and the staff was friendly."

Reviewed on Apr 13, 2025

Hilton Garden Inn Dulles North
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is $106 per night from May 11 to May 12
$106
includes taxes & fees
May 11 - May 12
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! (1,006 reviews)
"Hotel was located in a convenient spot for dining and shopping however you can hear traffic from the highway. Room was clean and updated. Staff helpful."

Reviewed on Apr 17, 2025

Comfort Inn & Suites
Clarion Hotel & Conference Center Leesburg
Clarion Hotel & Conference Center Leesburg
2.5 out of 5
1500 E Market St, Leesburg, VA
The price is $109 per night from May 6 to May 7
$109
includes taxes & fees
May 6 - May 7
Book a stay at this business-friendly hotel in Leesburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6.6/10 (1,000 reviews)
"Good time"

Reviewed on Apr 5, 2025

Clarion Hotel & Conference Center Leesburg
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
The price is $135 per night from May 4 to May 5
$135
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,002 reviews)
"Whenever we passed this area, we stayed."

Reviewed on Apr 22, 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 692 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.