Deals on vacations and trips to Upperville

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Upperville flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Save 100% on your flight
Price was $502, price is now $359 per person
$359
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
A 24-hour gym, self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and luggage storage are also provided.
Hilton Alexandria Old Town

Hilton Alexandria Old Town

4 out of 5
Old Town Alexandria
Price was $1,056, price is now $720 per person
$720
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the express check-in and WiFi in public areas. Self parking, a terrace, and limo/town car service are also offered.
Homewood Suites by Hilton Washington DC Capitol-Navy Yard

Homewood Suites by Hilton Washington DC Capitol-Navy Yard

3 out of 5
Navy Yard
Save 100% on your flight
Price was $614, price is now $428 per person
$428
per person
Dec 5 - Dec 10
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and free buffet breakfast each morning.
William F. Bolger Center

William F. Bolger Center

3 out of 5
Save 100% on your flight
Price was $538, price is now $387 per person
$387
per person
Dec 5 - Dec 10
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (IAD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Top Upperville hotels deals

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Free Cancellation
Reserve now, pay when you stay
$272 nightly
The price is $310 total per night
$310 total
Oct 13 - Oct 14
Total with taxes and fees
This smoke-free resort features a golf course, 3 outdoor tennis courts, and a restaurant. There's fun for all ages with a waterslide and a playground, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the business center, laundry service, and airport shuttle.
Pool
Pet friendly
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
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $118 total per night
$118 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking and a free area shuttle.
Pool
Free airport shuttle
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $120 total per night
$120 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 out of 5
4328 William L Wilson Fwy, Harpers Ferry, WV
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $103 total per night
$103 total
Nov 3 - Nov 4
Total with taxes and fees
A casino, a 24-hour gym, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $75 total per night
$75 total
Nov 2 - Nov 3
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's express check-out and multilingual staff can provide around-the-clock assistance.
Pet friendly
Parking included
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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.

Popular places to visit

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.

Upperville Park

Frequently asked questions

How much are vacation packages to Upperville?
Enjoy a one-of-a-kind experience in Upperville with a vacation package starting at just $359. Organizing your hotels, flights and tours through Travelocity is simple. On top of that, our deals will leave you with extra cash for loads of fun activities.
Where can I get the best vacation package deals for Upperville?
For an excellent package deal to Upperville, turn to Travelocity. Select from 400 air carriers and 1,000,000 properties worldwide to create the ideal trip — it's really that simple.
Why should I book my Upperville vacation bundle via Travelocity?
With first-rate service, 24/7 customer support and some of the most amazing getaways imaginable, you'll never wander alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.
Will I save money on my Upperville car rental if I bundle it with a hotel or flight?
With an Upperville vacation package, you can combine your car, flight and hotel bookings and save a nice amount. If you're in the mood to uncover the best of this awesome city, why not start with White House? This renowned sight is 45 mi from Upperville. With a rental car, you'll be there in the blink of an eye.
Which airport is best for Upperville?
For plenty of travelers, a trip to Upperville means coming in to land at Ronald Reagan Washington National Airport (DCA). This bustling airport sits 45 mi east of the city center. You could also choose to fly into Washington Dulles Intl. Airport (IAD) (25 mi away from central Upperville) or Hagerstown Regional Airport (HGR) (50 mi away from central Upperville).
Where should I stay when visiting Upperville?
Many visitors choose to stay at the Cozy Country Getaway in the Heart of Upperville. It's a terrific base for your Upperville vacation.

Photos of local treasures

Browse Upperville vacation photos for more inspiration