Upperville Vacations from $209

Book a Hotel + Flight or Car together to unlock savings

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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.
Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $341, price is now $209 per person
$209
per person
Jan 30 - Feb 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,011 reviews)
Everything was perfect. Clean Room, Nice Staff and beautiful hotel.

Reviewed on Nov 3, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $529, price is now $294 per person
$294
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,099 reviews)
IT WAS A VERY GOOD TIME FOR ME HAVE STIAD @ THE VIRGIN RIVER.AND THAT HOW WE'LL THEY TERIATED AND I WOULD LIKE TO KNOW HOW MUCH A ROOM.COSTS PER NIGHT

Reviewed on Nov 2, 2025

Hilton Alexandria Old Town

Hilton Alexandria Old Town

4 out of 5
Old Town Alexandria
Save 100% on your flight
Price was $675, price is now $379 per person
$379
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,006 reviews)
Nice clean parking was underground parking garage but was safe and clean.

Reviewed on Nov 1, 2025

Kimpton George Hotel by IHG

Kimpton George Hotel by IHG

4.5 out of 5
Northwest
Save 100% on your flight
Price was $649, price is now $397 per person
$397
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,007 reviews)
The hotel is OK, not much more.

Reviewed on Oct 29, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $897, price is now $559 per person
$559
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (2,000 reviews)
Great location! The hotel was definitely a value for the price. Clean and well maintained. We got a corner room and it was very quiet. The free snacks and drinks in the evening are a nice perk!

Reviewed on Nov 3, 2025

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Upperville Hotel Deals

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 Nov 5 to Nov 6
$75 total
Nov 5 - Nov 6
Total with taxes and fees
8.4/10 Very Good! (1,119 reviews)
Clean room, great location.

Reviewed on Nov 3, 2025

Travelodge by Wyndham Winchester
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $98 total per night from Nov 23 to Nov 24
$98 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Room was clean. Checkin staff was very courteous. Breakfast was not too lavish but decent for the price. So overall we were quite pleased with the stay

Reviewed on Nov 1, 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
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $116 total per night from Dec 1 to Dec 2
$116 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (2,198 reviews)
Sheets were comfy, towels were a reasonable size, overall would recommend.

Reviewed on Nov 2, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 722 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 $209 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.