Upperville Vacations from $249

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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.
Studio 6 Springfield, Va – Washington Dc Southwest

Studio 6 Springfield, Va – Washington Dc Southwest

2 out of 5
Price was $313, price is now $249 per person
$249
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
7.8/10 Good! (135 reviews)
Kitchen was a plus, lack of pots pans dishes and utensils were a minus.

Reviewed on Aug 11, 2025

Staybridge Suites Tysons - McLean by IHG

Staybridge Suites Tysons - McLean by IHG

3 out of 5
Save 100% on your flight
Price was $972, price is now $679 per person
$679
per person
Oct 26 - Oct 31
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to Washington (DCA)
9.2/10 Wonderful! (1,002 reviews)
Need to weed the front planters and pick up the trash. Not a very good first impression. Ms. Angel was nice and professional. Please upgrade the property. The life guard was nice.

Reviewed on Jul 30, 2025

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Save 100% on your flight
Price was $411, price is now $315 per person
$315
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
it had a nice clean gym

Reviewed on Aug 17, 2025

Landing Washington DC near Washington Navy Yard

Landing Washington DC near Washington Navy Yard

2 out of 5
Southeast
Save 100% on your flight
Price was $670, price is now $528 per person
$528
per person
Sep 19 - Sep 22
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
Hilton Garden Inn Reagan National Airport

Hilton Garden Inn Reagan National Airport

3.5 out of 5
Crystal City
Price was $404, price is now $332 per person
$332
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,694 reviews)
The people at the front desk were not very personable but the hotel was really nice and clean.

Reviewed on Aug 19, 2025

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Upperville Hotel Deals

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
$103 nightly
The price is $112 total per night from Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (2,126 reviews)
"Loved this hotel Clean, friendlt staff, great breakfast and dog friendly"

Reviewed on Aug 14, 2025

La Quinta Inn & Suites by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
$272 nightly
The price is $310 total per night from Sep 1 to Sep 2
$310 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Excellent couples getaway for Fourth of July, including great fireworks display. The pools and spa/fitness amenities are top notch and charming historic Leesburg is a 10-minute drive from the property."

Reviewed on Aug 11, 2025

Lansdowne 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
Fully refundable
$85 nightly
The price is $92 total per night from Aug 24 to Aug 25
$92 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (1,002 reviews)
"Bed comfort"

Reviewed on Aug 12, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 701 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.

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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 $249 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.