Upperville Vacations from $515

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Your Upperville Vacation

Take the worry out of organizing your next exciting adventure with an Upperville vacation package. Whether you're here for its art, food, architecture or something else, you'll find countless exciting experiences to delve into. Like some inspiration on what to see or do first during your trip to Upperville? Don't miss top attractions such as Sky Meadows State Park. Whoever you're traveling with and whether your budget is big or small, your ultimate Upperville vacation is just clicks away with Expedia.

The Latest Upperville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
Save 100% on your flight
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Washington (DCA)
8.8/10 Excellent! (1,340 reviews)
Great place to stay in the heart of Georgetown.

Reviewed on Jun 2, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 17 - Aug 23
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,025 reviews)
staffs are great, but the property is very old. It has nothing in the room. No flat iron no closet. It doesn’t worth that much money.

Reviewed on Jun 6, 2024

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 17 - Aug 23
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
Was only there for one business night and it’s very convenient. Large rooms and very clean

Reviewed on Jun 5, 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug 17 - Aug 23
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,005 reviews)
It's location. However the hotel is very small and old.

Reviewed on Jun 7, 2024

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Aug 17 - Aug 23
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
The Watergate is a great property, you can tell it looks a little aged and in need of renovations. Overall we enjoyed our stay.

Reviewed on Jun 2, 2024

Upperville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Barrel Oak Winery, The Boxwood Winery and Philip Carter Winery

Upperville Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is $116 per night from Jun 9 to Jun 10
$116
$126 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (1,366 reviews)
"Friendly staff, easy check in, clean, close to SU, convenient to restaurants."

Reviewed on Jun 3, 2024

La Quinta Inn & Suites by Wyndham Winchester
Clarion Hotel & Conference Center Leesburg
Clarion Hotel & Conference Center Leesburg
2.5 out of 5
1500 E Market St, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is $117 per night from Jun 9 to Jun 10
$117
$135 total
includes taxes & fees
Jun 9 - Jun 10
6.8/10 (876 reviews)
"Very courteous front desk staff despite our late arrival."

Reviewed on May 26, 2024

Clarion Hotel & Conference Center Leesburg
Lansdowne Resort and Spa
Lansdowne Resort and Spa
4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is $219 per night from Jul 2 to Jul 3
$219
$285 total
includes taxes & fees
Jul 2 - Jul 3
8.4/10 Very Good! (845 reviews)
"Beautiful property very kid friendly"

Reviewed on Jun 2, 2024

Lansdowne Resort and Spa
See all 647 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Upperville vacation package cost?
Starting from an incredible $515, you can handcraft your own Upperville package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Upperville?
Our Upperville vacation packages mean plenty of savings for the savvy wanderer. For the best deal, simply bundle your flights, hotels and activities into one neat package. But impressive bargains are just the beginning of your next unforgettable adventure. When you book with Expedia, you’ll have more than 550 airlines and 1,000,000 properties around the globe to pick from. Whatever your budget or style, there’s a vacation package with your name on it.
How far in advance should I book my Upperville vacation?
It all depends on the air carrier, but you can normally browse through international airfares on Expedia nearly a year in advance. While it’s generally a good idea to book ahead of time, lucky travelers will sometimes nab a cheaper flight just weeks prior to the date of departure.
What does an Expedia Upperville travel package include?
Expedia has all you need to plan your Upperville getaway, but what goes into your package is totally up to you. Choose from a combination of hotels, rental cars and flights. Looking for some activities to keep you on the go? Once you’ve made your booking, you can add them on too. No matter your budget or style, there’s a package to meet your needs.
What should I know before booking an Upperville travel package?
So many places to visit, so many things to see. With a package, you’ll be able to cross more of them off your list. Bundle your flights, rental cars and hotels and get set to save.
Can I choose my airline with an Upperville Expedia vacation package?
Yes, and with over 550 airlines to select from globally, you’re not short on choice. Look through the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Upperville vacation package?
Plans can change in a flash, so yes, you can. You may be able to cancel or alter your Upperville vacation package for free if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.