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Upperville

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Upperville Flights as Low as $98

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

Frontier Airlines
Fri, Sep 5 - Mon, Sep 8
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$98 Roundtrip, found 4 days ago
$98
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Mon, Sep 8, priced at $98 found 4 days ago
Frontier Airlines
Sat, Aug 30 - Tue, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$101 Roundtrip, found 4 days ago
$101
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Sep 9, priced at $101 found 4 days ago
Frontier Airlines
Sat, Aug 30 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$103 Roundtrip, found 20 hours ago
$103
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Sep 6, priced at $103 found 20 hours ago
Frontier Airlines
Sun, Sep 7 - Sat, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Sep 13, priced at $108 found 5 days ago
American Airlines
Tue, Nov 11 - Wed, Nov 12
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 8 hours ago
$137
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Nov 11 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, Nov 12, priced at $137 found 8 hours ago
American Airlines
Sat, Oct 25 - Mon, Oct 27
CLT
Charlotte-Douglas Intl.
DCA
Ronald Reagan Washington National
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Oct 25 from Charlotte-Douglas Intl. to Ronald Reagan Washington National, returning Mon, Oct 27, priced at $139 found 3 days ago
American Airlines
Thu, Oct 23 - Sun, Oct 26
CLT
Charlotte-Douglas Intl.
IAD
Washington Dulles Intl.
$145 Roundtrip, found 17 hours ago
$145
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Thu, Oct 23 from Charlotte-Douglas Intl. to Washington Dulles Intl., returning Sun, Oct 26, priced at $145 found 17 hours ago
United
Thu, Oct 23 - Sun, Oct 26
CLT
Charlotte-Douglas Intl.
IAD
Washington Dulles Intl.
$145 Roundtrip, found 17 hours ago
$145
Roundtrip
found 17 hours ago
Select United flight, departing Thu, Oct 23 from Charlotte-Douglas Intl. to Washington Dulles Intl., returning Sun, Oct 26, priced at $145 found 17 hours ago
Delta
Fri, Oct 24 - Wed, Oct 29
CLT
Charlotte-Douglas Intl.
DCA
Ronald Reagan Washington National
$177 Roundtrip, found 17 hours ago
$177
Roundtrip
found 17 hours ago
Select Delta flight, departing Fri, Oct 24 from Charlotte-Douglas Intl. to Ronald Reagan Washington National, returning Wed, Oct 29, priced at $177 found 17 hours ago
Frontier Airlines
Mon, Oct 6 - Sat, Oct 11
ORD
O'Hare Intl.
IAD
Washington Dulles Intl.
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Oct 6 from O'Hare Intl. to Washington Dulles Intl., returning Sat, Oct 11, priced at $183 found 2 days ago
United
Wed, Sep 17 - Mon, Sep 22
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Ronald Reagan Washington National, returning Mon, Sep 22, priced at $197 found 12 hours ago
JetBlue Airways
Tue, Nov 18 - Sat, Nov 22
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Nov 18 from O'Hare Intl. to Ronald Reagan Washington National, returning Sat, Nov 22, priced at $203 found 2 days ago
Delta
Sat, Nov 8 - Sat, Nov 8
DAL
Love Field
DCA
Ronald Reagan Washington National
$231 Roundtrip, found 8 hours ago
$231
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Nov 8 from Love Field to Ronald Reagan Washington National, returning Sat, Nov 8, priced at $231 found 8 hours ago
Delta
Mon, Sep 22 - Wed, Sep 24
DAL
Love Field
IAD
Washington Dulles Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Delta flight, departing Mon, Sep 22 from Love Field to Washington Dulles Intl., returning Wed, Sep 24, priced at $237 just found
KLM
Tue, Aug 26 - Thu, Sep 11
NBO
Jomo Kenyatta Intl.
IAD
Washington Dulles Intl.
$1,517 Roundtrip, found 11 hours ago
$1,517
Roundtrip
found 11 hours ago
Select KLM flight, departing Tue, Aug 26 from Jomo Kenyatta Intl. to Washington Dulles Intl., returning Thu, Sep 11, priced at $1,517 found 11 hours ago
Ethiopian Airlines
Sat, Aug 23 - Thu, Sep 11
NBO
Jomo Kenyatta Intl.
IAD
Washington Dulles Intl.
$1,901 Roundtrip, found 11 hours ago
$1,901
Roundtrip
found 11 hours ago
Select Ethiopian Airlines flight, departing Sat, Aug 23 from Jomo Kenyatta Intl. to Washington Dulles Intl., returning Thu, Sep 11, priced at $1,901 found 11 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 September, 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 $98, 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 $98 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$97

Last Minute Hotel Deals in Upperville

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 ...
9.2/10 Wonderful! (2,129 reviews)
"Loved this hotel Clean, friendlt staff, great breakfast and dog friendly"

Reviewed on Aug 14, 2025

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La Quinta Inn & Suites by Wyndham Winchester
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)
"Excellent couples getaway for Fourth of July, including great fireworks display. The pools and spa/fitness amenities are top notch and charming historic Leesburg is a 10-minute drive from the property."

Reviewed on Aug 11, 2025

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Lansdowne 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
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)
"Bed comfort"

Reviewed on Aug 12, 2025

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Holiday Inn Winchester Se-Historic Gateway by IHG
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! (1,318 reviews)
"Very quiet, carpets felt somewhat yuckie bc it is a pet place. Air conditioning worked very well."

Reviewed on Aug 12, 2025

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Microtel Inn & Suites by Wyndham Winchester
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
Stay at this 5-star luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...
9/10 Wonderful! (360 reviews)
The Salamander is exquisite - the perfect stay.
"The Salamander is exquisite—luxurious and sophisticated. Its style and design are flawless, and the entire experience is top tier. You truly can’t go wrong with a stay at this beautiful resort; it’s the perfect getaway for any occasion."

Reviewed on Aug 5, 2025

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Salamander Resort And Spa
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET, 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 ...
9.4/10 Exceptional! (693 reviews)
"Nice work"

Reviewed on Aug 20, 2025

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SpringHill Suites by Marriott 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 parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,002 reviews)
"I was very happy with my stay here. They had a friendly and efficient staff and clean rooms. The hot breakfast was good and there were some nice options to choose from. I will reserve here again next time I’m in the area!"

Reviewed on Aug 19, 2025

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Best Western Leesburg Hotel & Conference Center
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! (1,001 reviews)
"First time"

Reviewed on Aug 16, 2025

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Hilton Garden Inn Dulles North
See all 701 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.