Search Cheap Flights to
Upperville

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Upperville Flights as Low as $78

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

Frontier Airlines
Sat, Sep 26 - Thu, Oct 15
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$78 Roundtrip, found 3 hours ago
$78
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Thu, Oct 15, priced at $78 found 3 hours ago
Frontier Airlines
Tue, Aug 11 - Sat, Aug 22
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$80 Roundtrip, found 8 hours ago
$80
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Aug 22, priced at $80 found 8 hours ago
Frontier Airlines
Tue, Aug 4 - Tue, Aug 18
LAS
Harry Reid Intl.
IAD
Washington Dulles Intl.
$105 Roundtrip, found 3 days ago
$105
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Harry Reid Intl. to Washington Dulles Intl., returning Tue, Aug 18, priced at $105 found 3 days ago
Delta
Sat, Aug 15 - Mon, Aug 24
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$169 Roundtrip, found 10 hours ago
$169
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Aug 15 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Mon, Aug 24, priced at $169 found 10 hours ago
United
Sat, Sep 26 - Thu, Oct 15
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$169 Roundtrip, found 3 hours ago
$169
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Thu, Oct 15, priced at $169 found 3 hours ago
Delta
Sat, Sep 26 - Thu, Oct 15
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$169 Roundtrip, found 3 hours ago
$169
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Thu, Oct 15, priced at $169 found 3 hours ago
American Airlines
Sat, Aug 15 - Mon, Aug 24
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$169 Roundtrip, found 10 hours ago
$169
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Aug 15 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Mon, Aug 24, priced at $169 found 10 hours ago
Delta
Tue, Aug 11 - Wed, Aug 26
MSP
Minneapolis - St. Paul Intl.
DCA
Ronald Reagan Washington National
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 11 from Minneapolis - St. Paul Intl. to Ronald Reagan Washington National, returning Wed, Aug 26, priced at $191 found 4 days ago
Frontier Airlines
Tue, Sep 8 - Wed, Sep 9
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Sep 8 from George Bush Intercontinental to Washington Dulles Intl., returning Wed, Sep 9, priced at $210 found 6 days ago
United
Mon, Aug 17 - Tue, Aug 18
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select United flight, departing Mon, Aug 17 from George Bush Intercontinental to Ronald Reagan Washington National, returning Tue, Aug 18, priced at $218 found 1 day ago
Frontier Airlines
Wed, Aug 12 - Tue, Sep 1
LAS
Harry Reid Intl.
DCA
Ronald Reagan Washington National
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Harry Reid Intl. to Ronald Reagan Washington National, returning Tue, Sep 1, priced at $219 found 3 days ago
Frontier Airlines
Tue, Aug 11 - Wed, Aug 12
MSP
Minneapolis - St. Paul Intl.
IAD
Washington Dulles Intl.
$220 Roundtrip, found 11 hours ago
$220
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Minneapolis - St. Paul Intl. to Washington Dulles Intl., returning Wed, Aug 12, priced at $220 found 11 hours ago
JetBlue Airways
Mon, Aug 17 - Tue, Aug 18
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Aug 17 from George Bush Intercontinental to Ronald Reagan Washington National, returning Tue, Aug 18, priced at $291 found 1 day ago
Alaska Airlines
Wed, Aug 12 - Tue, Sep 1
LAS
Harry Reid Intl.
DCA
Ronald Reagan Washington National
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Aug 12 from Harry Reid Intl. to Ronald Reagan Washington National, returning Tue, Sep 1, priced at $299 found 3 days ago
United
Thu, Aug 6 - Mon, Aug 17
SUX
Sioux Gateway
DCA
Ronald Reagan Washington National
$403 Roundtrip, found 1 day ago
$403
Roundtrip
found 1 day ago
Select United flight, departing Thu, Aug 6 from Sioux Gateway to Ronald Reagan Washington National, returning Mon, Aug 17, priced at $403 found 1 day ago
United
Wed, Jul 22 - Wed, Aug 5
SUX
Sioux Gateway
IAD
Washington Dulles Intl.
$534 Roundtrip, found 11 hours ago
$534
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Jul 22 from Sioux Gateway to Washington Dulles Intl., returning Wed, Aug 5, priced at $534 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 $78, 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 $78 right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$78

Last Minute Hotel Deals in Upperville

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! (1,031 reviews)
"Everything was great except for the fact the shower was terrible. It felt like it took me an hour just to rinse the sham out of my hair because the water was coming out in a slow trickle. It was so bad I thought I would have to just rinse my head under the sink!"

Reviewed on Jul 10, 2026

Get rates
TRU 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! (1,009 reviews)
"My daughter and I stayed at Landdown resort for 2 nights. We used the pools and ate in 2 of the restaurants. Coton and Rye was hit and miss. Our first meal was great, but the second dinner was not. To be fair, tbe resrt did comp my meal and I was grateful. The pools were adequate, but could do with ..."

Reviewed on Jul 11, 2026

Get rates
Lansdowne 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 ...
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on Jul 5, 2026

Get rates
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! (404 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

Get rates
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 ...
9.2/10 Wonderful! (1,015 reviews)
"Very clean and nicely decorated property"

Reviewed on Jul 11, 2026

Get rates
Holiday Inn Winchester Se-Historic Gateway by IHG
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! (1,016 reviews)
"Although we booked a room same day and was able to get a room during the July 4th Holiday, the hotel was not very helpful. When asked about a shuttle for getting to and from airport we were advised yes they did. However the next day when we went to take a shuttle to airport we were told its on the ..."

Reviewed on Jul 9, 2026

Get rates
Hilton Garden Inn Dulles North
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 ...
9.4/10 Exceptional! (90 reviews)
"$25 amenities fee + tax. No amenities, simple elegant boutique hotel in town, but no amenities. $30 surprise valet parking + tip. Overpriced. Next time, we will stay at another hotel. But try the restaurant(s)."

Reviewed on Jul 12, 2026

Get rates
Hotel Burg
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! (1,016 reviews)
"Very good restaurant and staff. Highly recommend This hotel it's very old but up to date,large well furnished rooms and great bed."

Reviewed on Jul 8, 2026

Get rates
The George Washington Hotel, A Wyndham Grand Hotel
See all 754 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.