Upperville Vacations

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

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Upperville Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Kasa Del Ray Alexandria

Kasa Del Ray Alexandria

4 out of 5
Potomac West
Price was $706, price is now $660 per person
$660
per person
Jun 15 - Jun 19
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Washington (DCA)
Stay at this aparthotel in Alexandria. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions MGM National Harbor Casino and Nationals Park are located nearby.

Elegant Apartments Near the Pentagon

Elegant Apartments Near the Pentagon

3.5 out of 5
Crystal City
Price was $1,494, price is now $1,167 per person
$1,167
per person
Jun 14 - Jun 19
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Washington (DCA)
Book a stay at this business-friendly apartment in Arlington. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions National Mall and White House are located nearby.

Well Appointed Apartments W Full Comfort

Well Appointed Apartments W Full Comfort

3.5 out of 5
Crystal City
Price was $1,436, price is now $1,126 per person
$1,126
per person
Jun 14 - Jun 19
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Washington (DCA)
Stay at this apartment in Arlington. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions National Mall and White House are located nearby.

Serene DC-Area Apartments

Serene DC-Area Apartments

3.5 out of 5
Crystal City
Price was $1,387, price is now $1,093 per person
$1,093
per person
Jun 14 - Jun 19
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Washington (DCA)
Stay at this apartment in Arlington. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Nationals Park and National Mall are located nearby.

Heart of DC Area Apartments

Heart of DC Area Apartments

3.5 out of 5
Crystal City
Price was $1,496, price is now $1,250 per person
$1,250
per person
Jun 14 - Jun 19
found 4 hours ago
Roundtrip flight included
Denver (DEN) to Washington (DCA)
Stay at this apartment in Arlington. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions National Mall and Nationals Park are located nearby.

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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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
26.89 km from city center
Book a stay at this business-friendly hotel in Front Royal. 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 ...
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive Winchester VA
34.98 km from city center
Book a stay at this business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise 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
Sat, May 16 - Mon, May 18
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 16 from Orlando Intl. to Washington Dulles Intl., returning Mon, May 18, priced at $108 found 5 days ago
Delta
Sat, May 16 - Wed, May 20
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$150 Roundtrip, found 5 days ago
$150
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, May 16 from Orlando Intl. to Ronald Reagan Washington National, returning Wed, May 20, priced at $150 found 5 days ago
American Airlines
Wed, May 13 - Tue, May 19
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, May 13 from Logan Intl. to Ronald Reagan Washington National, returning Tue, May 19, priced at $157 found 3 days ago
United
Sat, May 16 - Tue, May 19
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$163 Roundtrip, found 5 days ago
$163
Roundtrip
found 5 days ago
Select United flight, departing Sat, May 16 from Orlando Intl. to Washington Dulles Intl., returning Tue, May 19, priced at $163 found 5 days ago
Southwest Airlines
Wed, May 13 - Wed, May 20
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, May 13 from Orlando Intl. to Ronald Reagan Washington National, returning Wed, May 20, priced at $217 found 4 days ago