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
Book a stay at this golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Book a stay at this luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Hilton Garden Inn Dulles North
22400 Flagstaff Plaza Ashburn VA
Book a stay at this business-friendly hotel in Ashburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
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 ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Hotel Burg
208 S King Street Leesburg VA
Stay at this hotel in Leesburg. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Popular attractions Gleedsville Art Gallery and Earth and Fire Gallery are ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Best Western Leesburg Hotel & Conference Center
726 E Market St Leesburg VA
Book a stay at this business-friendly hotel in Leesburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Clarion Inn Harpers Ferry - Charles Town
4328 William L Wilson Fwy Harpers Ferry WV
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 ...
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.
Mon, Aug 24 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$98
Roundtrip
found 1 day ago
Tue, Nov 3 - Tue, Nov 17
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$147
Roundtrip
found 6 hours ago
Tue, Nov 3 - Tue, Nov 17
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$147
Roundtrip
found 6 hours ago
Tue, Sep 29 - Tue, Oct 6
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$147
Roundtrip
found 5 hours ago
Fri, Sep 11 - Mon, Sep 28
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$172
Roundtrip
found 1 day ago
Best points of interest in Upperville
- Shenandoah National Park Vacations
- Hollywood Casino at Charles Town Races Vacations
- Jiffy Lube Live Vacations
- Front Royal Entrance Shenandoah National Park Vacations
- Shenandoah River Vacations
- King SPA Vacations
- Summit Point Motorsports Park Vacations
- Shenandoah University Vacations
- George Washington National Forest Vacations
- Leesburg Premium Outlets Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations