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Find hotels in Upperville, VA from ￥10,372

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Dec 23 - Dec 24
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Dec 24 - Dec 25
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Dec 26 - Dec 28
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Jan 2 - Jan 4

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Our top choices for Upperville hotels

Breakfast, lunch, dinner served; American cuisine
Hilton Garden Inn Haymarket

Hilton Garden Inn Haymarket

Hilton Garden Inn Haymarket
3.0 star property
Haymarket
9.4 out of 10, Exceptional, (253)
"Nice hotel in a hallmark town "
United States
Diane
The price is ￥20,659
￥23,965 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hilton Garden Inn Haymarket
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
Inn at Evergreen
2 bars/lounges, sports bar
Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1003)
"Certainly will stay again "
United States
philip
The price is ￥10,001
￥11,302 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Rodeway Inn & Suites Charles Town
Lobby
Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
Charles Town
8.0 out of 10, Very Good, (1000)
"The room is clean. The staff is friendly. The breakfast was good. No-frills hotel, but clean and efficient. "
United States
Kelsey
The price is ￥10,333
￥11,677 total
includes taxes & fees
Dec 28 - Dec 29
Days Inn by Wyndham Charles Town/Harpers Ferry
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, (1009)
"Great hotel!"
United States
CHARLES
The price is ￥19,871
￥22,514 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The George Washington Hotel, A Wyndham Grand Hotel
Front of property
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is ￥25,114
￥28,379 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Carriage Inn B&B
2 restaurants, breakfast, lunch served; local and international cuisine
Goodstone Inn & Restaurant

Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (48)
"It was a delightful quaint exclusive country inn - a real treat to stay. "
United States
Amanda
The price is ￥59,465
￥81,742 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Goodstone Inn & Restaurant
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, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is ￥16,804
￥18,283 total
includes taxes & fees
Jan 11 - Jan 12, 2026
SpringHill Suites by Marriott Winchester
Indoor pool
Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (993)
"Friendly staff, clean room, good breakfast "
United States
Vivian
The price is ￥15,367
￥17,518 total
includes taxes & fees
Dec 30 - Dec 31
Hampton Inn by Hilton Gainesville-Haymarket
Outdoor dining
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern
4.0 star property
Downtown
9.6 out of 10, Exceptional, (408)
"Staff was super nice, room was lovely, overall an amazing stay. "
United States
Audrey
The Red Fox Inn & Tavern
Standard Studio, Non Smoking, Refrigerator & Microwave | Desk, iron/ironing board, free WiFi, bed sheets
Extended Stay America Select Suites Gainesville

Extended Stay America Select Suites Gainesville

Extended Stay America Select Suites Gainesville
2.5 star property
Gainesville
6.2 out of 10, (480)
"Amazing place "
United States
Evelyn
The price is ￥12,001
￥13,857 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Extended Stay America Select Suites Gainesville
Free daily buffet breakfast
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, (2239)
"The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. "
United States
Jordyn
The price is ￥15,502
￥16,867 total
includes taxes & fees
Jan 1 - Jan 2, 2026
La Quinta Inn & Suites by Wyndham Winchester
Exterior
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (919)
"comfortable room, amenities and staff"
United States
Prashant
The price is ￥15,956
￥17,359 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Courtyard by Marriott Winchester
Reception
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North
3.0 star property
Ashburn
8.4 out of 10, Very Good, (1003)
"Nice stay. "
Canada
Ebrahim
The price is ￥13,773
￥15,702 total
includes taxes & fees
Dec 30 - Dec 31
Hilton Garden Inn Dulles North
Rooftop terrace
Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG
2.5 star property
Charles Town
9.2 out of 10, Wonderful, (1004)
"Nice place to stay "
United States
Wendy
The price is ￥15,533
￥17,552 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Charles Town by IHG
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
The price is ￥23,700
￥30,467 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hillbrook Inn
Exterior
Salamander Resort And Spa

Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (373)
"."
Canada
Ivanti
The price is ￥79,862
￥99,192 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Salamander Resort And Spa
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, (1003)
"Have stayed here multiple times -always good"
United States
Robert
The price is ￥12,979
￥14,121 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Country Inn & Suites by Radisson, Winchester, VA
Garden
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (174)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is ￥34,135
￥37,652 total
includes taxes & fees
Jan 7 - Jan 8, 2026
L'Auberge Provencale Inn & Restaurant
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, (1005)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is ￥12,866
￥14,470 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!"
David 1-night trip
Posted 14 hours ago
Comfort Inn & Suites Winchester

More cheap stays in Upperville

Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton

7379 Comfort Inn Drive Warrenton VA
The price is ￥9,668 per night from Jan 7 to Jan 8
￥9,668
￥10,372 total
Jan 7 - Jan 8, 2026
includes taxes & fees
6.4/10 (1,003 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.
What are some of the best vacation home rentals in Upperville?
The Apple Mountain House: This vacation home rental outside of Upperville is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all 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.

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