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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Washington (DCA)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 4 onsite conference rooms. A gym is on site, and self parking and a 24-hour front desk are also offered.
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Washington (DCA)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a terrace and multilingual staff can provide around-the-clock assistance.
The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Washington (DCA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. A terrace, limo/town car service, and a lobby fireplace are also on offer.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This aparthotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Limo/town car service, a computer station, and dry cleaning are also on offer.
Landing Washington DC near Washington Navy Yard

Landing Washington DC near Washington Navy Yard

2 out of 5
Southeast
Save 100% on your flight
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This aparthotel includes free WiFi in public areas and a virtual front desk.

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
$252 nightly
The price is $287 total per night
$287 total
Sep 1 - Sep 2
Total includes 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
$104 nightly
The price is $113 total per night
$113 total
Sep 1 - Sep 2
Total includes 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
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
$96 nightly
The price is $104 total per night
$104 total
Aug 17 - Aug 18
Total includes 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
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $86 total per night
$86 total
Sep 2 - Sep 3
Total includes 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
Clarion Hotel & Conference Center Leesburg

Clarion Hotel & Conference Center Leesburg

2.5 out of 5
1500 E Market St, Leesburg, VA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features a gym and a seasonal outdoor pool. 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
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
$641 nightly
The price is $730 total per night
$730 total
Sep 1 - Sep 2
Total includes 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
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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 $285. 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