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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was $392, price is now $247 per person
$247
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was $877, price is now $401 per person
$401
per person
Apr 1 - Apr 4
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.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was $1,645, price is now $790 per person
$790
per person
Feb 21 - Feb 28
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.
Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $1,201, price is now $723 per person
$723
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
The hotel's 24-hour gym, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Self parking, a coffee shop, and dry cleaning are also offered.
Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $1,680, price is now $1,027 per person
$1,027
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy a meal from the restaurant and perks like free WiFi.

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
$206 nightly
The price is $235 total per night
$235 total
Jan 25 - Jan 26
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
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
$92 nightly
The price is $104 total per night
$104 total
Jan 25 - Jan 26
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
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
$596 nightly
The price is $679 total per night
$679 total
Jan 15 - Jan 16
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
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
$82 nightly
The price is $89 total per night
$89 total
Jan 26 - Jan 27
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
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
$92 nightly
The price is $100 total per night
$100 total
Jan 15 - Jan 16
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
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
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $143 total per night
$143 total
Jan 20 - Jan 21
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
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 $247. 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