Upperville Vacations from $321

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Your Upperville Vacation

When you choose a Upperville vacation package, you can relax and enjoy your getaway to the fullest. Uncover the sights and sounds of this fascinating city knowing that everything has been taken care of in advance. During your trip to Upperville, take all the time you need for sightseeing. A fantastic place to begin is Sky Meadows State Park. Expedia is here to help you escape the everyday. Tailor your vacation to Upperville to match your travel style, whatever that may be.

The Latest Upperville vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (848 reviews)
It was ok but the area is not good

Reviewed on Jul 11, 2025

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 14 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,007 reviews)
Great location. Good food. Friendly staff.

Reviewed on Jul 12, 2025

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,008 reviews)
This hotel is very dated. No USB/C connections in the rooms. Very small bathrooms. The elevators are old & small as well. They have a bar/restaurant on the property and when we walked in was like going back to the 80s. Bar is very old. Oh, I almost forgot they $44 per night for parking

Reviewed on Jul 11, 2025

Holiday Inn Washington Capitol - Natl Mall by IHG

Holiday Inn Washington Capitol - Natl Mall by IHG

3 out of 5
Southwest
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (2,808 reviews)
We love staying at this hotel. It's very close to the metro, so you can access all of DC. It's walking distance to the Mall with all the Smithsonian museums. It's clean, it's quiet, and it's perfect.

Reviewed on Jul 11, 2025

Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

3.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (2,282 reviews)
Everyone here was very kind thank you

Reviewed on Jul 12, 2025

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Upperville Hotel Deals

Lansdowne Resort and Spa
Lansdowne Resort and Spa
4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
$262 nightly
The price is $298 total per night from Jul 16 to Jul 17
$298 total
Jul 16 - Jul 17
Total includes taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Excellent hotel with great pool."

Reviewed on Jul 6, 2025

Lansdowne Resort and Spa
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
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $126 total per night from Jul 20 to Jul 21
$126 total
Jul 20 - Jul 21
Total includes taxes and fees
9/10 Wonderful! (2,075 reviews)
"Safe and quiet. Esdy parking"

Reviewed on Jul 10, 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Jul 16 to Jul 17
$75 total
Jul 16 - Jul 17
Total includes taxes and fees
8.4/10 Very Good! (1,100 reviews)
"Staff friendly and helpful.. room was clean and bed very comfortable."

Reviewed on Jul 9, 2025

Travelodge by Wyndham Winchester
See all 706 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.

Find the Best Upperville Vacation Packages

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

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Frequently asked questions

How much does an Upperville vacation package cost?
You can snap up a vacation package to this popular destination from $321 on Expedia. But how much your vacation to Upperville costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Upperville?
You can typically find lower prices and greater availability in February, November and December. Take a look at our cheap Upperville vacation packages and you could score some great off-season deals.
How many days is enough for Upperville?
Generally, a handful of days is enough to check out the main attractions during your Upperville vacation. However, if you want to have time to rest or take day tours, consider extending your trip.
How to find the best Upperville package deals?
Begin your search for an Upperville package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Upperville package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Upperville escape off to a flying start.
Is it cheaper to book an Upperville vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Upperville vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Upperville?
If you're considering a spur-of-the-moment Upperville trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Upperville vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Upperville break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.