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Upperville

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Upperville Flights as Low as $96

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

Frontier Airlines
Fri, Jul 25 - Sat, Jul 26
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$96 Roundtrip, found 3 days ago
$96
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jul 25 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Jul 26, priced at $96 found 3 days ago
Frontier Airlines
Thu, Jul 24 - Sun, Jul 27
MIA
Miami Intl.
IAD
Washington Dulles Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jul 24 from Miami Intl. to Washington Dulles Intl., returning Sun, Jul 27, priced at $110 found 2 days ago
Frontier Airlines
Fri, Jul 18 - Sat, Jul 19
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Orlando Intl. to Washington Dulles Intl., returning Sat, Jul 19, priced at $112 found 5 days ago
JetBlue Airways
Wed, Nov 5 - Wed, Nov 5
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Wed, Nov 5 from Orlando Intl. to Ronald Reagan Washington National, returning Wed, Nov 5, priced at $122 found 9 hours ago
Delta
Tue, Sep 9 - Tue, Sep 16
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$127 Roundtrip, found 9 hours ago
$127
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Sep 9 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Sep 16, priced at $127 found 9 hours ago
American Airlines
Tue, Sep 9 - Tue, Sep 16
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$127 Roundtrip, found 9 hours ago
$127
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 9 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Sep 16, priced at $127 found 9 hours ago
Delta
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$134 Roundtrip, found 2 hours ago
$134
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Aug 30, priced at $134 found 2 hours ago
American Airlines
Mon, Sep 8 - Mon, Sep 8
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 9 hours ago
$137
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Mon, Sep 8 from Logan Intl. to Ronald Reagan Washington National, returning Mon, Sep 8, priced at $137 found 9 hours ago
American Airlines
Tue, Oct 28 - Tue, Nov 4
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 28 from Miami Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $147 found 1 day ago
United
Thu, Aug 7 - Sun, Aug 10
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$168 Roundtrip, found 14 hours ago
$168
Roundtrip
found 14 hours ago
Select United flight, departing Thu, Aug 7 from Logan Intl. to Washington Dulles Intl., returning Sun, Aug 10, priced at $168 found 14 hours ago
Frontier Airlines
Wed, Jul 9 - Thu, Jul 10
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$173 Roundtrip, found 5 days ago
$173
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jul 9 from Denver Intl. to Ronald Reagan Washington National, returning Thu, Jul 10, priced at $173 found 5 days ago
United
Fri, Aug 22 - Sun, Aug 24
DEN
Denver Intl.
IAD
Washington Dulles Intl.
$203 Roundtrip, found 6 days ago
$203
Roundtrip
found 6 days ago
Select United flight, departing Fri, Aug 22 from Denver Intl. to Washington Dulles Intl., returning Sun, Aug 24, priced at $203 found 6 days ago
Accessrail
Tue, Oct 28 - Tue, Nov 4
AVT
Aventura Brightline Train Station
DCA
Ronald Reagan Washington National
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Accessrail flight, departing Tue, Oct 28 from Aventura Brightline Train Station to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $302 found 1 day ago
Accessrail
Tue, Oct 28 - Tue, Nov 4
EKW
Miami Central Brightline Train Station
DCA
Ronald Reagan Washington National
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Accessrail flight, departing Tue, Oct 28 from Miami Central Brightline Train Station to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $302 found 1 day ago
Accessrail
Thu, Jul 10 - Sun, Jul 13
AVT
Aventura Brightline Train Station
IAD
Washington Dulles Intl.
$798 Roundtrip, found 18 hours ago
$798
Roundtrip
found 18 hours ago
Select Accessrail flight, departing Thu, Jul 10 from Aventura Brightline Train Station to Washington Dulles Intl., returning Sun, Jul 13, priced at $798 found 18 hours ago
Accessrail
Thu, Jul 10 - Sun, Jul 13
EKW
Miami Central Brightline Train Station
IAD
Washington Dulles Intl.
$798 Roundtrip, found 18 hours ago
$798
Roundtrip
found 18 hours ago
Select Accessrail flight, departing Thu, Jul 10 from Miami Central Brightline Train Station to Washington Dulles Intl., returning Sun, Jul 13, priced at $798 found 18 hours 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 July, 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 $96, 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 $96 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$95

Last Minute Hotel Deals in Upperville

Lansdowne Resort and Spa
Lansdowne Resort and Spa
4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
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! (1,004 reviews)
"Beautiful resort, very good restaurants on site, everyone was very friendly!"

Reviewed on Jul 3, 2025

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Lansdowne Resort and Spa
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,119 reviews)
"Good place for the price, complimentary breakfast was nice"

Reviewed on Jul 3, 2025

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Travelodge by Wyndham Winchester
Hilton Garden Inn Dulles North
Hilton Garden Inn Dulles North
3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
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! (1,003 reviews)
"evything fine"

Reviewed on Jun 27, 2025

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Hilton Garden Inn Dulles North
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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"The room was nice and the beds comfortable; however, people were out in the hallway late at night making a lot of noise. Also, we prefer a buffet breakfast - the served breakfast just takes too long for people on the road for work."

Reviewed on Jul 5, 2025

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Holiday Inn Winchester Se-Historic Gateway by IHG
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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,070 reviews)
"Nice staff, good breakfast and coffee. Bed was a little uncomfortable but rest of my family slept well."

Reviewed on Jul 3, 2025

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La Quinta Inn & Suites by Wyndham Winchester
Clarion Hotel & Conference Center Leesburg
Clarion Hotel & Conference Center Leesburg
2.5 out of 5
1500 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 helpful staff in our reviews. ...
6.6/10 (1,000 reviews)
Nice clean hotel
"This is an older hotel that could certainly use an update or two but for its age it was jept very ckean and had all the expected amenities. Was just there for an overnight leisure stay but had time to enjoy the pool and would be willing to stay there again."

Reviewed on Jun 30, 2025

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Clarion Hotel & Conference Center Leesburg
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
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! (1,000 reviews)
"This hotel has really friendly staff, thoughtful touches like magazines in the lobby, the ability to store our stuff for a couple hours after checkout, and a solid breakfast buffet but the rooms are a little run down."

Reviewed on Jun 26, 2025

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Clarion Inn Harpers Ferry - Charles Town
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,290 reviews)
"Very clean, quiet and comfortable."

Reviewed on Jul 3, 2025

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Microtel Inn & Suites by Wyndham Winchester
See all 710 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.