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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Price was $692, price is now $493 per person
$493
per person
Jun 25 - Jun 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.
Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $783, price is now $539 per person
$539
per person
Jun 18 - Jun 22
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a snack bar/deli, and luggage storage are also offered.
Heart of DC Area Apartments

Heart of DC Area Apartments

3.5 out of 5
Crystal City
Save 100% on your flight
Price was $993, price is now $748 per person
$748
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This apartment features an outdoor pool and an indoor pool. Enjoy the 24-hour gym and perks like free WiFi. Self parking and express check-out are also offered on site.
DC Charm in Crystal Apartments

DC Charm in Crystal Apartments

3 out of 5
Price was $952, price is now $724 per person
$724
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This apartment features free WiFi in public areas, barbecue grills, and self parking. A business center, a garden, and a picnic area are also on offer.
Washington Dulles Marriott Suites

Washington Dulles Marriott Suites

3.5 out of 5
Price was $773, price is now $595 per person
$595
per person
Jun 11 - Jun 15
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Washington (IAD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. Free self parking, a coffee shop, and limo/town car service 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
The price is $302 total per night
$302 total
per night
Apr 26 - Apr 27
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
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
The price is $679 total per night
$679 total
per night
May 10 - May 11
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
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
The price is $140 total per night
$140 total
per night
May 10 - May 11
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
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is $138 total per night
$138 total
per night
Apr 26 - Apr 27
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Pool
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
Free Cancellation
The price is $103 total per night
$103 total
per night
Apr 19 - Apr 20
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
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
The price is $126 total per night
$126 total
per night
Apr 19 - Apr 20
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
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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 $493. 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

Welcome sign to Upperville Virginia in Fauquier County.
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