Deals on vacations and trips to Upperville

Save when you book Upperville package deals

Choose two or more items and save on your trip:

Upperville flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
Save 100% on your flight
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Families will appreciate the children's pool and picnic area. Enjoy the outdoor pool and perks like free WiFi.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A restaurant and a bar/lounge are featured at this hotel. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.
Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.
The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Make the most of the gym and a rooftop terrace, and relax with drinks at one of the 3 bars/lounges.
Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Limo/town car service, a snack bar/deli, and luggage storage are also on offer.

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
Get rates
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
Get rates
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
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
Free Cancellation
Get rates
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking 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
Get rates
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
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
Free Cancellation
Reserve now, pay when you stay
Get rates
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, and arcade/game room. Enjoy the gym and perks like free WiFi.
Pool
Spa
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
Get rates
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
Don't see what you're looking for?
See all available properties in Upperville
View all properties
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 $610. 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