Upperville Vacations from $178

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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.
Econo Lodge Fredericksburg near I-95

Econo Lodge Fredericksburg near I-95

2 out of 5
Price was $222, price is now $178 per person
$178
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
6.4/10 (266 reviews)
Great service, very clean, and safe

Reviewed on Jul 4, 2025

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
Price was $406, price is now $303 per person
$303
per person
Nov 6 - Nov 9
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to Washington (DCA)
8/10 Very Good! (852 reviews)
The staff was very friendly, the rooms were clean, they are remodeling. The one disappointment for me was Pet Friendly and some people's pet aren't clean.

Reviewed on Aug 18, 2025

Hilton Garden Inn Fredericksburg

Hilton Garden Inn Fredericksburg

3 out of 5
Save 100% on your flight
Price was $412, price is now $318 per person
$318
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
8.2/10 Very Good! (1,009 reviews)
Why we need to pay for a parking??????? First time time on my life here about charging for parking in hotel

Reviewed on Aug 15, 2025

Courtyard by Marriott Tysons McLean

Courtyard by Marriott Tysons McLean

3 out of 5
Save 100% on your flight
Price was $846, price is now $665 per person
$665
per person
Oct 28 - Nov 1
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Room was nice. I didn't really like my view but overall everything was nice

Reviewed on Aug 3, 2025

Country Inn & Suites by Radisson, Fredericksburg South (I-95), VA

Country Inn & Suites by Radisson, Fredericksburg South (I-95), VA

3 out of 5
Price was $331, price is now $264 per person
$264
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
7.8/10 Good! (1,002 reviews)
This property is very convenient, complete with dining not a minute away! Our unit was extremely tired. The bathroom was in poor condition, the tub was very dirty, the door didn’t close and the floor needs repair. Both mattresses were very uncomfortable and not even. The bananas in the lobby were tired, not fresh. The breakfast was very good.

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! (2,133 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on Aug 19, 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
$252 nightly
The price is $287 total per night from Sep 1 to Sep 2
$287 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,004 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 31 to Sep 1
$92 total
Aug 31 - Sep 1
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 $178 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.