Upperville Vacations from $274

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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 AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $378, price is now $274 per person
$274
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Washington (DCA)
9/10 Wonderful! (1,205 reviews)
Beautiful stay. No microwave for the guest unless you have suite but that didnt change my experience.

Reviewed on Nov 5, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $723, price is now $416 per person
$416
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,178 reviews)
Love the staff and location!

Reviewed on Dec 5, 2025

SIXTY DC

SIXTY DC

4.5 out of 5
Downtown Washington D.C.
Price was $548, price is now $387 per person
$387
per person
Feb 13 - Feb 15
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (76 reviews)
Absolutely amazing! Johnny made our stay extra special! Will stay here again!

Reviewed on Dec 3, 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $708, price is now $508 per person
$508
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,681 reviews)
The woman who checked us in was very pleasant and kind…she left the desk to go to the door and actually show me where to access the parking garage.

Reviewed on Dec 5, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was $409, price is now $297 per person
$297
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,084 reviews)
Beautiful accommodations and very accommodating staff.

Reviewed on Dec 3, 2025

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Upperville Hotel Deals

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
$69 nightly
The price is $79 total per night from Jan 4 to Jan 5
$79 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4/10 Very Good! (1,012 reviews)
The room was clean and spacious, and the options for breakfast were plentiful. Eggs, potatoes, bacon, and sausage were available in the warmers while the more traditional continental breakfast items were also available. Staff was very friendly and helpful. The pool was a great place to hang out between ...

Reviewed on Nov 24, 2025

Hilton Garden Inn Dulles North
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $231 total per night from Jan 1 to Jan 2
$231 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
Yes

Reviewed on Dec 1, 2025

Lansdowne Resort and Spa
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
$591 nightly
The price is $673 total per night from Dec 15 to Dec 16
$673 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (370 reviews)
It’s a great hotel. However, they don’t have non-Tesla EV chargers, nor adapters for other cars. That’s already odd, given this is a fancy hotel next to DC. But it’s even odder that they don’t tell you that there’s a (paid) EV charger in the parking lot of the Town Hall, *literally* next door to ...

Reviewed on Dec 1, 2025

Salamander Resort And Spa
See all 716 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 $274 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.