Upperville Vacation Packages 2026 from $387

Upperville flight + hotel vacation packages

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

Sheraton Pentagon City Hotel

$387

per person

Jun 24 - Jun 27

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 business center, express check-in, and free airport shuttle. A free shopping center shuttle is offered as well.

InterContinental Washington D.C. - The Wharf by IHG

Southwest

$452

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.

Placemakr Buzzard Point

Southwest

Save 100% on your flight

$704

per person

Jun 24 - Jun 27

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

YOTEL Washington DC

Northwest

Save 100% on your flight

$442

per person

Jun 4 - Jun 7

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, conference center, and conference space. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.

Hilton Washington DC Capitol Hill

Northwest

Save 100% on your flight

$425

per person

Jun 25 - Jun 28

found 1 day 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.

Top Upperville hotels deals

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA

Free Cancellation

Reserve now, pay when you stay

$265 nightly

$302 total

Apr 26 - Apr 27

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

Salamander Resort And Spa

500 North Pendleton Street Middleburg VA

Free Cancellation

Reserve now, pay when you stay

$596 nightly

$679 total

May 10 - May 11

Total with taxes and fees

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

22400 Flagstaff Plaza Ashburn VA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$140 total

May 10 - May 11

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

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$138 total

Apr 26 - Apr 27

Total with taxes and fees

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

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$92 total

Apr 19 - Apr 20

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

Free Cancellation

$92 nightly

$100 total

May 17 - May 18

Total with taxes and fees

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

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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.

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 $387. 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.