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Upperville

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Upperville Flights as Low as $68

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

Frontier Airlines
Wed, Sep 9 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$68 Roundtrip, found 8 hours ago
$68
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Fri, Sep 11, priced at $68 found 8 hours ago
Frontier Airlines
Wed, Sep 9 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$75 Roundtrip, found 8 hours ago
$75
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Fri, Sep 11, priced at $75 found 8 hours ago
Frontier Airlines
Wed, Sep 9 - Wed, Sep 23
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$92 Roundtrip, found 8 hours ago
$92
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Orlando Intl. to Washington Dulles Intl., returning Wed, Sep 23, priced at $92 found 8 hours ago
Breeze Airways
Fri, Aug 28 - Mon, Aug 31
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$94 Roundtrip, found 8 hours ago
$94
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Aug 28 from Orlando Intl. to Washington Dulles Intl., returning Mon, Aug 31, priced at $94 found 8 hours ago
JetBlue Airways
Sat, Sep 5 - Sun, Sep 6
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 5 from Logan Intl. to Ronald Reagan Washington National, returning Sun, Sep 6, priced at $119 found 1 day ago
Delta
Sat, Sep 5 - Sun, Sep 6
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 5 from Logan Intl. to Ronald Reagan Washington National, returning Sun, Sep 6, priced at $119 found 1 day ago
Delta
Sat, Sep 5 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$172 Roundtrip, found 11 hours ago
$172
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Fri, Sep 11, priced at $172 found 11 hours ago
Southwest Airlines
Sat, Sep 5 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$172 Roundtrip, found 11 hours ago
$172
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Fri, Sep 11, priced at $172 found 11 hours ago
United
Sun, Sep 6 - Sun, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$172 Roundtrip, found 8 hours ago
$172
Roundtrip
found 8 hours ago
Select United flight, departing Sun, Sep 6 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sun, Sep 6, priced at $172 found 8 hours ago
American Airlines
Sat, Sep 5 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$172 Roundtrip, found 11 hours ago
$172
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Fri, Sep 11, priced at $172 found 11 hours ago
Frontier Airlines
Tue, Sep 1 - Tue, Sep 15
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Los Angeles Intl. to Ronald Reagan Washington National, returning Tue, Sep 15, priced at $178 found 1 day ago
Frontier Airlines
Fri, Aug 21 - Sat, Aug 29
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Aug 21 from Logan Intl. to Washington Dulles Intl., returning Sat, Aug 29, priced at $198 found 2 days ago
Southwest Airlines
Sat, Sep 12 - Sat, Sep 26
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$199 Roundtrip, found 11 hours ago
$199
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Orlando Intl. to Ronald Reagan Washington National, returning Sat, Sep 26, priced at $199 found 11 hours ago
JetBlue Airways
Tue, Sep 22 - Sat, Oct 3
JFK
John F. Kennedy Intl.
DCA
Ronald Reagan Washington National
$210 Roundtrip, found 4 days ago
$210
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Sep 22 from John F. Kennedy Intl. to Ronald Reagan Washington National, returning Sat, Oct 3, priced at $210 found 4 days ago
United
Sun, Nov 1 - Sat, Nov 7
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$257 Roundtrip, found 8 hours ago
$257
Roundtrip
found 8 hours ago
Select United flight, departing Sun, Nov 1 from Los Angeles Intl. to Washington Dulles Intl., returning Sat, Nov 7, priced at $257 found 8 hours ago
Alaska Airlines
Tue, Sep 1 - Tue, Sep 15
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Los Angeles Intl. to Ronald Reagan Washington National, returning Tue, Sep 15, priced at $307 found 1 day 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 $68, 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 $68 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$68

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! (1,007 reviews)
"I liked this place. It's not stellar, but it is full-service and pleasant. Plenty of things to do and the staff is competent."

Reviewed on Aug 5, 2026

Get rates
Lansdowne Resort and Spa
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! (410 reviews)
"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!!"

Reviewed on Jul 21, 2026

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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! (1,019 reviews)
"They were up grading the cabel nut it wasnt finished so didnt have much to watch when just trying to relax before thr next leg of our trip. Also it was a bit confusing when booked thought had free breakfast but then was told didnt have the upgrade never saw anything when booked with Expedia"

Reviewed on Aug 9, 2026

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Holiday Inn Winchester Se-Historic Gateway by IHG
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
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Spark by Hilton Winchester
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 ...
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Hilton Garden Inn Dulles North
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 a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,018 reviews)
"Great walking location to everything. Fancy historic building."

Reviewed on Aug 9, 2026

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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! (2,274 reviews)
"We only stayed for one night, but enjoyed the room and how close it was to shopping and attractions"

Reviewed on Aug 9, 2026

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La Quinta Inn & Suites by Wyndham Winchester
Hotel Burg

Hotel Burg

4 out of 5
208 S King Street Leesburg VA
Stay at this hotel in Leesburg. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Popular attractions Gleedsville Art Gallery and Earth and Fire Gallery are ...
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Hotel Burg
See all 739 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.