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Upperville

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Upperville Flights as Low as $60

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

Frontier Airlines
Tue, Jun 23 - Wed, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$60 Roundtrip, found 2 days ago
$60
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jun 23 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Jun 24, priced at $60 found 2 days ago
Frontier Airlines
Wed, May 27 - Fri, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Fri, May 29, priced at $68 found 1 day ago
Frontier Airlines
Wed, Aug 5 - Tue, Aug 25
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$86 Roundtrip, found 5 days ago
$86
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Tue, Aug 25, priced at $86 found 5 days ago
United
Tue, Jun 23 - Tue, Jun 30
CMH
John Glenn Columbus Intl.
IAD
Washington Dulles Intl.
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jun 23 from John Glenn Columbus Intl. to Washington Dulles Intl., returning Tue, Jun 30, priced at $140 found 3 days ago
Frontier Airlines
Wed, Aug 26 - Tue, Sep 8
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$150 Roundtrip, found 13 hours ago
$150
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Tue, Sep 8, priced at $150 found 13 hours ago
Delta
Tue, Jul 21 - Wed, Jul 22
CMH
John Glenn Columbus Intl.
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 21 from John Glenn Columbus Intl. to Ronald Reagan Washington National, returning Wed, Jul 22, priced at $157 found 2 days ago
Bargain Flight
Wed, Aug 12 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$184 Roundtrip, found 7 hours ago
$184
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, Aug 26, priced at $184 found 7 hours ago
American Airlines
Wed, Aug 12 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$189 Roundtrip, found 7 hours ago
$189
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, Aug 26, priced at $189 found 7 hours ago
American Airlines
Tue, Jul 21 - Tue, Aug 4
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 21 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Tue, Aug 4, priced at $197 found 2 days ago
JetBlue Airways
Tue, Jul 21 - Tue, Aug 4
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jul 21 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Tue, Aug 4, priced at $207 found 2 days ago
American Airlines
Tue, Aug 25 - Wed, Sep 2
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 25 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Wed, Sep 2, priced at $219 found 1 day ago
Frontier Airlines
Tue, Aug 4 - Tue, Aug 18
DEN
Denver Intl.
IAD
Washington Dulles Intl.
$230 Roundtrip, found 5 days ago
$230
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Denver Intl. to Washington Dulles Intl., returning Tue, Aug 18, priced at $230 found 5 days ago
Delta
Tue, Aug 25 - Wed, Sep 2
DAL
Love Field
DCA
Ronald Reagan Washington National
$239 Roundtrip, found 2 hours ago
$239
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Aug 25 from Love Field to Ronald Reagan Washington National, returning Wed, Sep 2, priced at $239 found 2 hours ago
Delta
Tue, Jun 9 - Wed, Jun 24
DAL
Love Field
IAD
Washington Dulles Intl.
$239 Roundtrip, found 3 days ago
$239
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 9 from Love Field to Washington Dulles Intl., returning Wed, Jun 24, priced at $239 found 3 days ago
Frontier Airlines
Wed, Sep 2 - Wed, Sep 16
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Denver Intl. to Ronald Reagan Washington National, returning Wed, Sep 16, priced at $254 found 1 day ago
Alaska Airlines
Fri, Sep 4 - Mon, Sep 7
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$546 Roundtrip, found 1 day ago
$546
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, Sep 4 from Denver Intl. to Ronald Reagan Washington National, returning Mon, Sep 7, priced at $546 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 June, 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 $60, 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 $60 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$59

Last Minute Hotel Deals in Upperville

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 ...
9/10 Wonderful! (1,004 reviews)
"Very clean hotel,friendly staff"

Reviewed on May 21, 2026

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Spark by Hilton Winchester
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! (1,000 reviews)
"Great stay"

Reviewed on May 12, 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! (396 reviews)
"The room was beautiful, very spacious and clean. We were on a wait list for the spa. Unfortunately, we were unable to get a massage."

Reviewed on May 20, 2026

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Salamander Resort And Spa
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court 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 in our reviews. ...
9/10 Wonderful! (873 reviews)
"Room very clean .. great to play pool .. but at breakfast had to ask for more oatmeal as it was empty even though the woman was standing right there. She was not paying attention to what was needed"

Reviewed on May 20, 2026

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TRU By Hilton Winchester
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! (1,001 reviews)
"Clean quiet and met expectations"

Reviewed on May 20, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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 helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,076 reviews)
"Very nice convenient and friendly. Highly recommend"

Reviewed on May 19, 2026

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Travelodge 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 WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,469 reviews)
"We always stay here. The rooms are clean and the staff is very friendly. We are never disappointed."

Reviewed on May 20, 2026

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Microtel Inn & Suites by Wyndham 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 ...
9/10 Wonderful! (1,001 reviews)
"Had trouble checking in. The lady could not find our reservation. Took some time for her to find it. Right now checking on why were charged more than what we were to be charged."

Reviewed on May 20, 2026

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Holiday Inn Winchester Se-Historic Gateway by IHG
See all 733 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.