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. ...
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 ...
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. ...
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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton

2.5 out of 5
7379 Comfort Inn Drive Warrenton VA
30.67 km from city center
Book a stay at this business-friendly motel in Warrenton. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff 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 ...
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 Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3 out of 5
100 Hollywood Dr Charles Town WV
33.71 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 helpful staff and the clean ...
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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
Tue, Aug 4 - Wed, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Aug 12, priced at $90 found 4 days ago
American Airlines
Tue, Oct 20 - Tue, Nov 3
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 20 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Nov 3, priced at $117 found 1 day ago
Delta
Tue, Oct 20 - Tue, Nov 3
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Nov 3, priced at $117 found 1 day ago
United
Tue, Sep 29 - Tue, Oct 6
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Sep 29 from Logan Intl. to Washington Dulles Intl., returning Tue, Oct 6, priced at $117 found 9 hours ago
Southwest Airlines
Sat, Aug 1 - Sat, Aug 8
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Aug 1 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Aug 8, priced at $192 found 4 days ago