Upperville Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
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 ...
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 ...
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
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. ...
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 ...
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 ...
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 ...
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
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 Loudoun Museum are located ...
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 ...
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 ...
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Front Royal Blue Ridge Shadows
111 Hospitality Drive Front Royal VA
Book a stay at this golf hotel in Front Royal. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our ...
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.
Sat, Oct 31 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$109
Roundtrip
found 3 days ago
Fri, Oct 2 - Mon, Oct 5
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$119
Roundtrip
found 6 days ago
Sat, Oct 31 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$137
Roundtrip
found 3 days ago
Mon, Oct 5 - Tue, Oct 6
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$145
Roundtrip
found 6 days ago
Tue, Oct 13 - Sat, Oct 17
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$169
Roundtrip
found 2 days ago
Best points of interest in Upperville
- Shenandoah National Park Vacations
- Jiffy Lube Live Vacations
- Hollywood Casino at Charles Town Races Vacations
- Front Royal Entrance Shenandoah National Park Vacations
- Shenandoah University Vacations
- King SPA Vacations
- Leesburg Premium Outlets Vacations
- Summit Point Motorsports Park Vacations
- Shenandoah River Vacations
- Stone Tower Winery 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