Upperville Vacations

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Upperville Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Washington (DCA)
Book a stay at this business-friendly hotel in Washington. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Washington (DCA)
Stay at this 5-star luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and National Museum of African American History and Culture are located nearby.

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Washington (DCA)
Stay at this 3.5-star business-friendly hotel in Arlington. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Arlington National Cemetery and Washington Monument are located nearby.

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Aug 28 - Sep 2
found 6 hours ago
Roundtrip flight included
San Francisco (SFO) to Washington (DCA)
Stay at this 5-star luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and 3 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions White House and Washington Monument are located nearby.

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Washington (DCA)
Stay at this 4-star eco-certified hotel in Washington. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Washington Monument are located nearby.

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Washington (DCA)
Stay at this 4-star hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Popular attractions Capital One Arena and Union Station Shopping Center 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
Stay at this 4-star golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
35 km from city center
Stay at this 3-star business-friendly hotel in Ashburn. Enjoy free WiFi, free parking, 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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast 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 breakfast and the helpful staff in our reviews. ...
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
12.56 km from city center
Stay at this 5-star 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 ...
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 ...
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 parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
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 ...
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 out of 5
10 S Commerce Ave, Front Royal, VA
27.26 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 helpful staff in our reviews. ...
Clarion Hotel & Conference Center Leesburg

Clarion Hotel & Conference Center Leesburg

2.5 out of 5
1500 E Market St, Leesburg, VA
33.23 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 in our reviews. ...
Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton

2.5 out of 5
7379 Comfort Inn Drive, U.S. 29, Warrenton, VA
30.67 km from city center
Book a stay at this business-friendly motel in Warrenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 ...
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
30.15 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, Sep 4 - Thu, Sep 11
TPA
Tampa Intl.
IAD
Washington Dulles Intl.
$121 Roundtrip, found 3 days ago
$121
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Tampa Intl. to Washington Dulles Intl., returning Thu, Sep 11, priced at $121 found 3 days ago
JetBlue Airways
Sun, Aug 24 - Sat, Sep 6
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Aug 24 from Orlando Intl. to Ronald Reagan Washington National, returning Sat, Sep 6, priced at $137 found 2 days ago
United
Sat, Aug 16 - Sun, Aug 17
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select United flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sun, Aug 17, priced at $147 found 6 days ago
Delta
Sat, Jul 5 - Mon, Jul 14
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jul 5 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Mon, Jul 14, priced at $168 found 2 days ago
American Airlines
Tue, Sep 2 - Tue, Sep 9
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$187 Roundtrip, found 3 hours ago
$187
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Sep 2 from Denver Intl. to Ronald Reagan Washington National, returning Tue, Sep 9, priced at $187 found 3 hours ago