Upperville Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

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 parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
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. ...
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 ...
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 ...
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. ...
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 ...
Salamander Middleburg

Salamander Middleburg

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 ...
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 golf hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
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 ...
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 ...
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 ...
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 ...
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4 out of 5
111 Hospitality Drive Front Royal VA
25.54 km from city center
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 ...
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 ...
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 ...
Don't see what you're looking for?
See all available properties in Upperville
View all properties
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 10 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$58 Roundtrip, found 6 days ago
$58
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Mon, Dec 14, priced at $58 found 6 days ago
Delta
Tue, Jan 5 - Sat, Jan 16
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jan 5 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Jan 16, priced at $137 found 3 days ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Dec 8, priced at $157 found 4 days ago
Southwest Airlines
Thu, Dec 10 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$163 Roundtrip, found 6 days ago
$163
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, Dec 15, priced at $163 found 6 days ago
American Airlines
Thu, Dec 10 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$163 Roundtrip, found 6 days ago
$163
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, Dec 15, priced at $163 found 6 days ago