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Upperville

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Upperville Flights as Low as $125

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

Frontier Airlines
Tue, Sep 22 - Wed, Oct 7
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Wed, Oct 7, priced at $125 found 3 days ago
United
Mon, Nov 23 - Thu, Nov 26
CVG
Cincinnati - Northern Kentucky Intl.
IAD
Washington Dulles Intl.
$131 Roundtrip, found 18 hours ago
$131
Roundtrip
found 18 hours ago
Select United flight, departing Mon, Nov 23 from Cincinnati - Northern Kentucky Intl. to Washington Dulles Intl., returning Thu, Nov 26, priced at $131 found 18 hours ago
Delta
Tue, Sep 29 - Mon, Oct 5
CVG
Cincinnati - Northern Kentucky Intl.
DCA
Ronald Reagan Washington National
$133 Roundtrip, found 18 hours ago
$133
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Sep 29 from Cincinnati - Northern Kentucky Intl. to Ronald Reagan Washington National, returning Mon, Oct 5, priced at $133 found 18 hours ago
American Airlines
Tue, Sep 29 - Mon, Oct 5
CVG
Cincinnati - Northern Kentucky Intl.
DCA
Ronald Reagan Washington National
$133 Roundtrip, found 18 hours ago
$133
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Sep 29 from Cincinnati - Northern Kentucky Intl. to Ronald Reagan Washington National, returning Mon, Oct 5, priced at $133 found 18 hours ago
Southwest Airlines
Tue, Sep 29 - Mon, Oct 5
CVG
Cincinnati - Northern Kentucky Intl.
DCA
Ronald Reagan Washington National
$153 Roundtrip, found 18 hours ago
$153
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Tue, Sep 29 from Cincinnati - Northern Kentucky Intl. to Ronald Reagan Washington National, returning Mon, Oct 5, priced at $153 found 18 hours ago
Frontier Airlines
Thu, Oct 8 - Wed, Oct 28
MSY
Louis Armstrong New Orleans Intl.
DCA
Ronald Reagan Washington National
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 8 from Louis Armstrong New Orleans Intl. to Ronald Reagan Washington National, returning Wed, Oct 28, priced at $156 found 3 days ago
Frontier Airlines
Thu, Oct 8 - Sat, Oct 24
MSY
Louis Armstrong New Orleans Intl.
IAD
Washington Dulles Intl.
$156 Roundtrip, just found
$156
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 8 from Louis Armstrong New Orleans Intl. to Washington Dulles Intl., returning Sat, Oct 24, priced at $156 just found
Frontier Airlines
Sat, Oct 3 - Sat, Oct 24
MSY
Louis Armstrong New Orleans Intl.
IAD
Washington Dulles Intl.
$159 Roundtrip, found 8 hours ago
$159
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Oct 3 from Louis Armstrong New Orleans Intl. to Washington Dulles Intl., returning Sat, Oct 24, priced at $159 found 8 hours ago
Frontier Airlines
Tue, Sep 22 - Wed, Oct 7
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Wed, Oct 7, priced at $161 found 3 days ago
Southwest Airlines
Wed, Nov 11 - Mon, Nov 16
DAL
Love Field
DCA
Ronald Reagan Washington National
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Nov 11 from Love Field to Ronald Reagan Washington National, returning Mon, Nov 16, priced at $222 found 5 days ago
Bargain Flight
Wed, Sep 2 - Tue, Sep 15
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$245 Roundtrip, just found
$245
Roundtrip
just found
Select Bargain Flight flight, departing Wed, Sep 2 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Tue, Sep 15, priced at $245 just found
Delta
Sat, Sep 5 - Fri, Sep 11
DAL
Love Field
IAD
Washington Dulles Intl.
$259 Roundtrip, found 5 days ago
$259
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Sep 5 from Love Field to Washington Dulles Intl., returning Fri, Sep 11, priced at $259 found 5 days ago
JetBlue Airways
Fri, Oct 16 - Mon, Nov 2
MSY
Louis Armstrong New Orleans Intl.
DCA
Ronald Reagan Washington National
$269 Roundtrip, found 3 days ago
$269
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Oct 16 from Louis Armstrong New Orleans Intl. to Ronald Reagan Washington National, returning Mon, Nov 2, priced at $269 found 3 days ago
Delta
Tue, Oct 27 - Sat, Nov 7
SHV
Shreveport Regional
DCA
Ronald Reagan Washington National
$327 Roundtrip, found 5 days ago
$327
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 27 from Shreveport Regional to Ronald Reagan Washington National, returning Sat, Nov 7, priced at $327 found 5 days ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
SHV
Shreveport Regional
IAD
Washington Dulles Intl.
$331 Roundtrip, found 1 hour ago
$331
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 26 from Shreveport Regional to Washington Dulles Intl., returning Tue, Sep 29, priced at $331 found 1 hour ago
Alaska Airlines
Sat, Sep 19 - Tue, Sep 22
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$596 Roundtrip, found 14 hours ago
$596
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Sat, Sep 19 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Tue, Sep 22, priced at $596 found 14 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 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 $125, 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 $125 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$125

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. ...
9/10 Wonderful! (1,006 reviews)
"The hotel property and staff were great. The service at the clubhouse restaurant was terrible. We didn’t get one of our meals until after everyone ese was already finished and had to ask to have it removed from the bill. Otherwise the hotel was lovely but the dining experience was sub par."

Reviewed on Aug 18, 2026

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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! (411 reviews)
"A really luxe resort. Outside pool area super good fun and great for kids and adults alike with separate areas. Well staffed in all areas of the hotel"

Reviewed on Aug 18, 2026

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Salamander Resort And Spa
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 ...
9.2/10 Wonderful! (1,011 reviews)
"The property and our room were well maintained and clean.The continental breakfast was nice, with a few added perks for the oatmeal, yogurt and bagels. The eating area was clean, and the coffee was good. We would stay again!"

Reviewed on Aug 18, 2026

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Spark by Hilton Winchester
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 ...
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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 a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,007 reviews)
"Beautiful hotel walkable to dinner and shops."

Reviewed on Aug 18, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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! (1,003 reviews)
"Clean room and experience, consistent with the Hilton Garden Inn brand."

Reviewed on Aug 17, 2026

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Hilton Garden Inn Dulles North
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 ...
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La Quinta Inn & Suites by Wyndham Winchester
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 parking, and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (1,437 reviews)
"Everything was very clean and new. The staff were all very helpful and nice. The road noise from the highway was disturbing. The water pressure was terrible and the 24 hour coffee was rarely fresh. I would also have liked more than one pillow."

Reviewed on Aug 17, 2026

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Microtel Inn & Suites by Wyndham Winchester
See all 731 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.