Upperville Vacations from $321

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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.
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 24 - Jul 27
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,512 reviews)
Love the hotel and staff

Reviewed on May 16, 2024

Hyatt Place National Harbor

Hyatt Place National Harbor

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 23
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (1,485 reviews)
It was awesome…wish I could’ve stayed longer!

Reviewed on May 15, 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
Jul 24 - Jul 27
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,008 reviews)
Great hotel, room and access to dining and museums.

Reviewed on May 13, 2024

Hotel Washington

Hotel Washington

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 24 - Jul 27
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,649 reviews)
Amazing staff, room, amenities and view!!! It is such a beautiful hotel

Reviewed on May 16, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Jul 11 - Jul 14
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,003 reviews)
It took 15 of running the water to get hot water for my shower and even though my ac was set at 68 the room temp never got below 71 even after a call to maintenance.

Reviewed on May 14, 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 $94 per night from May 22 to May 23
$94
$103 total
includes taxes & fees
May 22 - May 23
8.8/10 Excellent! (1,325 reviews)
"Very nice, newly constructed, hotel convenient and comfortable"

Reviewed on May 16, 2024

La Quinta Inn & Suites 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
Fully refundableReserve now, pay when you stay
The price is $84 per night from May 20 to May 21
$84
$92 total
includes taxes & fees
May 20 - May 21
8.8/10 Excellent! (758 reviews)
"Asked for 1st floor room or room near elevator-got neither"

Reviewed on May 14, 2024

Microtel 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 $105 per night from May 19 to May 20
$105
$120 total
includes taxes & fees
May 19 - May 20
6.6/10 (861 reviews)
"Great value"

Reviewed on May 12, 2024

Clarion Hotel & Conference Center Leesburg
See all 663 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

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Kid Friendly Vacations

Frequently asked questions

How much does an Upperville vacation package cost?
Starting from an incredible $321, 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.