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Find Romantic Hotels in Upperville, VA from $98

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Check availability on Upperville Romantic Hotels

Our top choices for Upperville romantic hotels

Exterior
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (779)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
$107 nightly
The price is $117
Dec 21 - Dec 22
Total with taxes and fees
SpringHill Suites by Marriott Winchester
Restaurant
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (846)
"Super friendly reception and perfectly clean room. "
United States
Dwight
$103 nightly
The price is $117
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA
Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1010)
"Great hotel!"
United States
CHARLES
$127 nightly
The price is $143
Dec 21 - Dec 22
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1002)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
$98 nightly
The price is $108
Dec 21 - Dec 22
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Dining
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
$89 nightly
The price is $98
Dec 16 - Dec 17
Total with taxes and fees
Wayside Inn
Restaurant
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
Charles Town
8.6 out of 10, Excellent, (523)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
$101 nightly
The price is $114
Dec 16 - Dec 17
Total with taxes and fees
The Inn at Charles Town - Hollywood Casino
Front of property
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
$173 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hillbrook Inn
Property amenity
Holiday Inn Express & Suites Leesburg - Historic District by IHG

Holiday Inn Express & Suites Leesburg - Historic District by IHG

Holiday Inn Express & Suites Leesburg - Historic District by IHG
2.5 star property
Leesburg
9.0 out of 10, Wonderful, (1002)
"Great stay! The king suite was spacious and clean! Would definitely stay at this location again. "
United States
Kaitlin
$105 nightly
The price is $121
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express & Suites Leesburg - Historic District by IHG
Interior
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (509)
"Great hotel"
United States
DONNA D
$95 nightly
The price is $108
Dec 22 - Dec 23
Total with taxes and fees
Hilton Garden Inn Winchester
Hallway
Inn at Evergreen

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (132)
"Very nice cozy place and the breakfast was included and very delicious. Only issue I had was the footsteps of upstairs guests came through."
United States
Chiharu
$206 nightly
The price is $235
Dec 17 - Dec 18
Total with taxes and fees
Inn at Evergreen
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.
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Top Upperville Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Comfortable and clean room."
Linda 1-night trip
Posted 6 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

Searching for romantic hotels in Upperville?
If you and your partner need some romantic time away, we've got just the thing. If you want to explore the area, you might head to Sky Meadows State Park or Upperville Park. If you'd like to stay close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Upperville?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Upperville: The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Upperville is 44 inches.
What is there to do in Upperville?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Upperville. You might consider a visit to Sky Meadows State Park or Upperville Park while you're in town.
What's the best way to get to Upperville and around town during my romantic getaway?
This information about transportation options in Upperville might help your romantic trip get off to a smooth start: To get to Upperville, you can fly into Washington Dulles Intl. Airport (IAD), which is the closest major airport, located 23.7 mi (38.2 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.

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