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Upperville

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Upperville Flights as Low as $82

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

Frontier Airlines
Wed, Aug 19 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$82 Roundtrip, found 3 days ago
$82
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Aug 25, priced at $82 found 3 days ago
Frontier Airlines
Fri, Sep 25 - Fri, Oct 16
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 25 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Fri, Oct 16, priced at $120 found 3 days ago
Frontier Airlines
Sat, Sep 26 - Sun, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sun, Oct 18, priced at $142 found 1 day ago
Frontier Airlines
Wed, Aug 19 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Aug 25, priced at $149 found 3 days ago
Bargain Flight
Wed, Oct 14 - Tue, Nov 3
CLT
Charlotte-Douglas Intl.
DCA
Ronald Reagan Washington National
$195 Roundtrip, found 6 hours ago
$195
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Wed, Oct 14 from Charlotte-Douglas Intl. to Ronald Reagan Washington National, returning Tue, Nov 3, priced at $195 found 6 hours ago
Bargain Flight
Tue, Jul 28 - Tue, Aug 4
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$197 Roundtrip, found 20 hours ago
$197
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Tue, Jul 28 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Aug 4, priced at $197 found 20 hours ago
Bargain Flight
Wed, Aug 12 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$200 Roundtrip, found 6 hours ago
$200
Roundtrip
found 6 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 $200 found 6 hours ago
Delta
Sun, Aug 2 - Wed, Aug 5
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$202 Roundtrip, found 4 days ago
$202
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Aug 2 from Logan Intl. to Ronald Reagan Washington National, returning Wed, Aug 5, priced at $202 found 4 days ago
JetBlue Airways
Wed, Aug 26 - Tue, Sep 15
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$210 Roundtrip, found 2 hours ago
$210
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Aug 26 from O'Hare Intl. to Ronald Reagan Washington National, returning Tue, Sep 15, priced at $210 found 2 hours ago
Frontier Airlines
Tue, Oct 6 - Tue, Oct 6
ORD
O'Hare Intl.
IAD
Washington Dulles Intl.
$210 Roundtrip, found 6 hours ago
$210
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Oct 6 from O'Hare Intl. to Washington Dulles Intl., returning Tue, Oct 6, priced at $210 found 6 hours ago
Frontier Airlines
Tue, Aug 11 - Tue, Aug 18
CLT
Charlotte-Douglas Intl.
IAD
Washington Dulles Intl.
$215 Roundtrip, found 2 hours ago
$215
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Charlotte-Douglas Intl. to Washington Dulles Intl., returning Tue, Aug 18, priced at $215 found 2 hours ago
American Airlines
Tue, Jul 21 - Wed, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$221 Roundtrip, found 6 days ago
$221
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Jul 21 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, Jul 22, priced at $221 found 6 days ago
United
Tue, Jul 21 - Tue, Aug 4
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$243 Roundtrip, found 1 hour ago
$243
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Jul 21 from Logan Intl. to Washington Dulles Intl., returning Tue, Aug 4, priced at $243 found 1 hour ago
JetBlue Airways
Sun, Aug 2 - Mon, Aug 24
PDX
Portland Intl.
DCA
Ronald Reagan Washington National
$349 Roundtrip, found 5 hours ago
$349
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sun, Aug 2 from Portland Intl. to Ronald Reagan Washington National, returning Mon, Aug 24, priced at $349 found 5 hours ago
Delta
Fri, Sep 18 - Mon, Sep 28
PDX
Portland Intl.
IAD
Washington Dulles Intl.
$357 Roundtrip, found 5 hours ago
$357
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Sep 18 from Portland Intl. to Washington Dulles Intl., returning Mon, Sep 28, priced at $357 found 5 hours ago
Alaska Airlines
Fri, Sep 18 - Mon, Sep 28
PDX
Portland Intl.
IAD
Washington Dulles Intl.
$357 Roundtrip, found 5 hours ago
$357
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Fri, Sep 18 from Portland Intl. to Washington Dulles Intl., returning Mon, Sep 28, priced at $357 found 5 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 August, 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 13 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 $82, 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 $82 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$82

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! (1,003 reviews)
"It’s a beautiful place but the rooms were fairly average. Nothing special. The shower was the worst part, it was either super hot or cold. Went to a trickle on medium. Couldn’t wash my hair! Also the breakfast buffet was $30 per person and not that great either. If you’re a golfer, you’d love it. ..."

Reviewed on Jul 3, 2026

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Lansdowne 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. ...
9.2/10 Wonderful! (1,008 reviews)
"Good location but floor was sticky in room and no closets, just open hooks."

Reviewed on Jul 4, 2026

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TRU By Hilton Winchester
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! (1,003 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on Jun 28, 2026

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Spark by Hilton Winchester
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! (403 reviews)
"Staff were very nice and knowledgeable about the history of the resort. My stay was very relaxing. I also enjoyed the zip-line tour. I recommend trying one of the salamander adventure activities."

Reviewed on Jul 3, 2026

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Salamander Resort And Spa
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! (1,006 reviews)
"Very charming historic hotel. Close to very nice restaurants and tourist District."

Reviewed on Jul 4, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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! (1,006 reviews)
"Comfortable clean room. Bathroom could use an upgrade. Shower head flow could not be changed to a softer setting. Also one of the few hotel chains that doesn’t offer a free breakfast. At $10 pp, Wawa is not far and has good food and coffee."

Reviewed on Jul 3, 2026

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Holiday Inn Winchester Se-Historic Gateway by IHG
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 Tally Ho Theatre are located ...
9.6/10 Exceptional! (86 reviews)
"Beware of the steep amenities fee upon checkout! This was a surprise and disappointment as it is not included in the rate. This fee includes coffee BUT coffee is ONLY available from 7am-8am in the morning. I am doubtful i will stay there again."

Reviewed on Jul 4, 2026

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Hotel Burg
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! (1,428 reviews)
"We live close by to the hotel and our air conditioner is not working during this heat wave. This was our second stay because of how friendly the staff is as well as being a clean property. The breakfast has multiple choices. Great hotel especially for the price."

Reviewed on Jul 3, 2026

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Microtel Inn & Suites by Wyndham Winchester
See all 751 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.