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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 , 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  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 , 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  right now, why wait?

Upperville Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Airlines serving
Alaska Airlines, American Airlines, Delta
Number of airlines serving
3
Roundtrip price
$256
Popular airline
American Airlines

Last Minute Hotel Deals in Upperville

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 breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,085 reviews)
Room was clean & heat worked properly. Parking was secure.

Reviewed on Nov 7, 2025

Travelodge by Wyndham Winchester
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
Stay at this 3-star 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! (1,000 reviews)
They don’t have curtains which make the room dark to sleep well. They have very thin and light curtains hanging in the middle and in the morning sunlight direct affects the bed and can’t sleep more after sunrise. All other was excellent, staff was excellent

Reviewed on Nov 4, 2025

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
Stay at this 3-star 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! (2,206 reviews)
Clean room, pleasant staff, ease of check-in and check-out

Reviewed on Nov 9, 2025

La Quinta Inn & Suites by Wyndham Winchester
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
Stay at this 5-star 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! (367 reviews)
The staff was really accommodating and the facilities were absolutely gorgeous!! Luxury and feeling like royalty the entire stay.

Reviewed on Nov 4, 2025

Salamander Resort And Spa
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 out of 5
4328 William L Wilson Fwy, Harpers Ferry, WV
Book a stay at this business-friendly hotel in Harpers Ferry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
7.8/10 Good! (1,050 reviews)
Everything was great except for the mattress that was very uncomfortable. The doors are heavy as well so when someone closes it you can hear it in your room. Could use paint on the doors.

Reviewed on Nov 4, 2025

Clarion Inn Harpers Ferry - Charles Town
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, 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 ...
9.4/10 Exceptional! (1,057 reviews)
Yes

Reviewed on Nov 4, 2025

Comfort Inn & Suites Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Stay at this 4-star golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
Appreciated the upgrade! Thank you

Reviewed on Oct 26, 2025

Lansdowne Resort and Spa
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 ...
9/10 Wonderful! (1,348 reviews)
We only stayed one night, but tge room was clean and comfortable.

Reviewed on Nov 9, 2025

Microtel Inn & Suites by Wyndham Winchester
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.