Upperville Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
Lansdowne Resort and Spa
44050 Woodridge Pkwy, Leesburg, VA
36.69 km from city center
Stay at this 4-star golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
29.56 km from city center
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
29.75 km from city center
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
32.95 km from city center
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Clarion Hotel & Conference Center Leesburg
1500 E Market St, Leesburg, VA
33.23 km from city center
Book a stay at this business-friendly hotel in Leesburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Salamander Resort And Spa
500 North Pendleton Street, Middleburg, VA
12.56 km from city center
Stay at this 5-star luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...
Hilton Garden Inn Dulles North
22400 Flagstaff Plaza, Ashburn, VA
35 km from city center
Stay at this 3-star business-friendly hotel in Ashburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Courtyard by Marriott Winchester
300 Marriott Drive, Winchester, VA
34.98 km from city center
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Holiday Inn Express Charles Town by IHG
681 Flowing Springs Rd, Charles Town, WV
34.77 km from city center
Book a stay at this business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd, Winchester, VA
30.04 km from city center
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Leesburg Hotel & Conference Center
726 E Market St, Leesburg, VA
32 km from city center
Book a stay at this business-friendly hotel in Leesburg. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Clarion Inn Harpers Ferry - Charles Town
4328 William L Wilson Fwy, Harpers Ferry, WV
37.58 km from city center
Book a stay at this business-friendly hotel in Harpers Ferry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd, Winchester, VA
30.14 km from city center
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Oct 7 - Tue, Oct 14
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Tue, Oct 7 - Tue, Oct 14
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Tue, Sep 2 - Tue, Sep 9
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Sat, Aug 23 - Mon, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$166 Roundtrip, found 4 days ago
$166
Roundtrip
found 4 days ago
Fri, Sep 5 - Sun, Sep 14
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Best points of interest in Upperville
- Shenandoah National Park Vacations
- Hollywood Casino at Charles Town Races Vacations
- Jiffy Lube Live Vacations
- Summit Point Motorsports Park Vacations
- Shenandoah River Vacations
- Front Royal Entrance Shenandoah National Park Vacations
- Winchester Medical Center Vacations
- Shenandoah University Vacations
- Morven Park Vacations
- George Washington National Forest Vacations
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