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. ...
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 ...
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
30.87 km from city center
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

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 ...
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 a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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 ...
Hotel Burg

Hotel Burg

4 out of 5
208 S King Street Leesburg VA
30.78 km from city center
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 ...
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 parking, and a fitness center. Our guests praise the helpful staff and ...
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. ...
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 ...
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
33.34 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 in our reviews. ...
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
33.19 km from city center
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

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 ...
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 ...
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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
Mon, Aug 24 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$78 Roundtrip, found 5 days ago
$78
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Sep 9, priced at $78 found 5 days ago
Delta
Fri, Sep 11 - Mon, Sep 28
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$139 Roundtrip, found 13 hours ago
$139
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Sep 11 from Logan Intl. to Ronald Reagan Washington National, returning Mon, Sep 28, priced at $139 found 13 hours ago
American Airlines
Tue, Oct 20 - Tue, Nov 3
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 20 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Nov 3, priced at $151 found 3 days ago
United
Tue, Sep 29 - Tue, Oct 6
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$151 Roundtrip, found 5 days ago
$151
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 29 from Logan Intl. to Washington Dulles Intl., returning Tue, Oct 6, priced at $151 found 5 days ago
JetBlue Airways
Tue, Oct 20 - Tue, Nov 3
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Oct 20 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Nov 3, priced at $151 found 3 days ago