Upperville Vacations

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Top Hotel Deals

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy Leesburg VA
36.69 km from city center
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. ...
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza Ashburn VA
35 km from city center
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 ...
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
12.53 km from city center
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

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
29.75 km from city center
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 ...
Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

2.5 out of 5
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 WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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
32.08 km from city center
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
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
29.53 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 ...
Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

2.5 out of 5
681 Flowing Springs Rd Charles Town WV
34.8 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 ...
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
29.68 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 ...
Holiday Inn Express & Suites Leesburg - Historic District by IHG

Holiday Inn Express & Suites Leesburg - Historic District by IHG

2.5 out of 5
80 Prosperity Ave Se Leesburg VA
31.71 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. ...
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
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 ...
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive Winchester VA
30.6 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

Clarion Hotel & Conference Center Leesburg

2.5 out of 5
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. ...
Home2 Suites by Hilton Charles Town

Home2 Suites by Hilton Charles Town

3 out of 5
70 Jefferson Crossing Way Charles Town WV
34.36 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 ...
Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket

2.5 out of 5
7300 Atlas Walk Way Gainesville VA
32.58 km from city center
Book a stay at this business-friendly hotel in Gainesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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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.

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.

Frontier Airlines
Sat, Apr 25 - Sat, May 9
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$76 Roundtrip, found 3 days ago
$76
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 9, priced at $76 found 3 days ago
Breeze Airways
Fri, May 8 - Mon, May 11
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 8 from Orlando Intl. to Washington Dulles Intl., returning Mon, May 11, priced at $134 found 1 day ago
United
Thu, May 7 - Sat, May 16
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select United flight, departing Thu, May 7 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 16, priced at $162 found 6 days ago
JetBlue Airways
Wed, Apr 22 - Sun, May 10
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Apr 22 from Orlando Intl. to Ronald Reagan Washington National, returning Sun, May 10, priced at $168 found 2 days ago
Delta
Thu, Apr 9 - Tue, Apr 14
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Apr 9 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, Apr 14, priced at $175 found 4 days ago