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Find hotels in Upperville, VA from ₩104,640

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Dec 19 - Dec 20
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Our top choices for Upperville hotels

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TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (770)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is ₩107,739
₩117,220 total
includes taxes & fees
Jan 12 - Jan 13, 2026
TRU By Hilton Winchester
Lobby
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1000)
"Have stayed here multiple times -always good"
United States
Robert
The price is ₩121,941
₩132,672 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1079)
"Very clean, helpful staff"
United States
Kathleen
The price is ₩145,366
₩158,159 total
includes taxes & fees
Dec 29 - Dec 30
Comfort Inn & Suites Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1383)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is ₩109,835
₩119,501 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Microtel Inn & Suites by Wyndham Winchester
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is ₩121,055
₩136,137 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Indoor pool
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1004)
"Very nice people in the front desk"
United States
Ximena
The price is ₩131,758
₩147,570 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Clarion Inn Harpers Ferry - Charles Town
Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Great location close to restaurants "
United States
SILVIA
The price is ₩113,792
₩128,926 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Spark by Hilton Winchester
Exterior
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1000)
"Great stay"
United States
Jaron
The price is ₩111,681
₩121,508 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Winchester
Exterior
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2226)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is ₩145,856
₩158,691 total
includes taxes & fees
Dec 21 - Dec 22
La Quinta Inn & Suites by Wyndham Winchester
Exterior
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (798)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is ₩136,777
₩148,815 total
includes taxes & fees
Dec 25 - Dec 26
Fairfield Inn & Suites by Marriott Winchester
Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout drapes
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (544)
"Very clean room, excellent staff!!!"
United States
James
The price is ₩115,194
₩125,332 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Candlewood Suites Winchester by IHG
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very Good, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is ₩106,292
₩115,646 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Pillowtop beds, desk, laptop workspace, blackout drapes
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, (783)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is ₩149,325
₩162,467 total
includes taxes & fees
Jan 11 - Jan 12, 2026
SpringHill Suites by Marriott Winchester
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
Front Royal
7.6 out of 10, Good, (1006)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
The price is ₩91,529
₩101,878 total
includes taxes & fees
Dec 25 - Dec 26
Super 8 by Wyndham Front Royal
Restaurant
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (915)
"comfortable room, amenities and staff"
United States
Prashant
The price is ₩149,325
₩162,466 total
includes taxes & fees
Dec 23 - Dec 24
Courtyard by Marriott Winchester
Reception
Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town
2.5 star property
Charles Town
9.4 out of 10, Exceptional, (1004)
"Quick check in friendly staff"
United States
Thomas
The price is ₩153,740
₩172,188 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Charles Town
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (1005)
"Great hotel!"
United States
CHARLES
The price is ₩186,971
₩211,839 total
includes taxes & fees
Dec 25 - Dec 26
The George Washington Hotel, A Wyndham Grand Hotel
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1089)
"Clean rooms, easy check in"
United States
Leslie
The price is ₩100,387
₩109,215 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Travelodge by Wyndham Winchester
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1005)
"great stay with breakfast too"
United States
James
The price is ₩99,481
₩108,234 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Sleep Inn & Suites Winchester near University
In-room safe, desk, iron/ironing board, bed sheets
TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (480)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is ₩158,110
₩172,024 total
includes taxes & fees
Dec 21 - Dec 22
TownePlace Suites by Marriott Winchester
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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Stay near popular Upperville attractions

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.
See properties

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

See all hotels in Upperville
Hiking Sky Meadows State Park...
Photo by Michael Gibson
Open Photo by Michael Gibson

Top Upperville Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Yes"
Mark 1-night trip
Posted 4 days ago
La Quinta Inn & Suites by Wyndham Winchester

More cheap stays in Upperville

Hampton Inn & Suites Williamsburg-Richmond Rd.

Hampton Inn & Suites Williamsburg-Richmond Rd.

1880 Richmond Rd Williamsburg VA
The price is ₩90,791 per night from Jan 4 to Jan 5
₩90,791
₩104,640 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9/10 Wonderful! (1,001 reviews)

Frequently asked questions

Where is the best place to stay in Upperville?
Located 21.7 mi (35 km) from the heart of Upperville, Hilton Garden Inn Dulles North is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Lansdowne Resort and Spa and Salamander Resort And Spa. See all available top hotels, or vacation rentals in Upperville.
If I need to cancel my hotel reservation in Upperville, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Upperville.
Where can I learn more about changing or cancelling my trip to Upperville?
To find more details about rescheduling or cancelling your trip to Upperville, head over to our customer service page.
What are some accommodations with pools in Upperville?
Hilton Garden Inn Dulles North: Features complimentary wired internet access, an indoor pool, and free self parking. Lansdowne Resort and Spa and Salamander Resort And Spa are a couple of other choices that offer an onsite pool. View all hotels with pools in Upperville.
What's the best hotel for staying near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
What's it like staying in Upperville?
Visitors can enjoy all that Upperville has to offer including its restaurants. In Upperville, there are 6 hotels and other accommodations to choose from. Find out more about Upperville.
What are the top places to visit in Upperville?
A couple of favorite places to visit are Sky Meadows State Park and Upperville Park. You'll also find Delaplane Cellars and RdV Vineyards in the area. Check out what more to see and do in Expedia's Upperville guide.
What's the seasonal weather like 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.