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 ...
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
29.77 km from city center
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. ...
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
29.56 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 ...
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
12.56 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 ...
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 out of 5
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 ...
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
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 ...
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 ...
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
30.14 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 ...
Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town

2.5 out of 5
157 Pimlico Dr Charles Town WV
34.35 km from city center
Stay at this hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
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
34.77 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 ...
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 ...
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 ...
Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA

2 out of 5
721 East Market Street Leesburg VA
31.8 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 and the clean ...
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET Winchester VA
33.26 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 ...
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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
Thu, Dec 25 - Thu, Jan 1
TPA
Tampa Intl.
IAD
Washington Dulles Intl.
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 25 from Tampa Intl. to Washington Dulles Intl., returning Thu, Jan 1, priced at $88 found 5 days ago
JetBlue Airways
Wed, Dec 24 - Wed, Dec 31
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$107 Roundtrip, found 16 hours ago
$107
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Wed, Dec 24 from Orlando Intl. to Ronald Reagan Washington National, returning Wed, Dec 31, priced at $107 found 16 hours ago
American Airlines
Fri, Dec 12 - Sun, Dec 14
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Dec 12 from Orlando Intl. to Ronald Reagan Washington National, returning Sun, Dec 14, priced at $137 found 2 days ago
United
Tue, Dec 9 - Fri, Dec 12
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Select United flight, departing Tue, Dec 9 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Fri, Dec 12, priced at $157 found 4 days ago
Delta
Mon, Nov 24 - Wed, Dec 3
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$182 Roundtrip, found 3 days ago
$182
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Nov 24 from Miami Intl. to Ronald Reagan Washington National, returning Wed, Dec 3, priced at $182 found 3 days ago