Photo by Michael Gibson
Find hotels in Upperville, VA from ฿2,077
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Our top choices for Upperville hotels
9.4 out of 10, Exceptional, (253)
Cosy haven near the famous concert venue, this business-friendly hotel combines convenience with comfort. Unwind in the 24-hour fitness centre after exploring Haymarket IcePlex. Enjoy American cuisine at Red House Tavern and free parking during your stay.
"Nice hotel in a hallmark town "
Diane
The price is ฿4,135
฿4,797 total
includes taxes & fees
1 Jan - 2 Jan 2026
9.4 out of 10, Exceptional, (132)
Surround yourself in recreational options at this boutique B&B featuring 4 tennis courts, an outdoor pool, and an on-site restaurant. After a day on the greens, unwind at the bar or terrace. Near Waterfall Park with free parking, WiFi, and breakfast.
"Very nice cozy place and the breakfast was included and very delicious. Only issue I had was the footsteps of upstairs guests came through."
Chiharu
8.6 out of 10, Excellent, (1003)
Positioned near Hollywood Casino at Charles Town Races, this motel offers complimentary breakfast, WiFi, and parking. Guests can dine at Alfredo's Mediterranean restaurant on site. Harpers Ferry National Historical Park is a short drive away. Staff receives high marks for helpfulness.
"Certainly will stay again "
philip
The price is ฿2,002
฿2,262 total
includes taxes & fees
11 Jan - 12 Jan 2026
Days Inn by Wyndham Charles Town/Harpers Ferry
Days Inn by Wyndham Charles Town/Harpers FerryCharles Town
8.0 out of 10, Very good, (1001)
Enjoy historic exploration with a convenient base near Hollywood Casino and Harpers Ferry National Park. Free continental breakfast starts your day, while the fitness centre helps maintain routines. Helpful staff and overall value make this Charles Town hotel an excellent choice.
"Nice place to stay"
Cynthia
The price is ฿2,069
฿2,337 total
includes taxes & fees
28 Dec - 29 Dec
The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand HotelOld Town Winchester
9.4 out of 10, Exceptional, (1009)
Relish this Winchester hotel's Georgian charm, with an indoor pool, full-service spa, and 2 restaurants including Uno's Pizzeria for dinner. The 24-hour fitness centre complements the prime location near Old Court House Civil War Museum and Bright Box Theatre.
"Great hotel!"
CHARLES
The price is ฿3,942
฿4,466 total
includes taxes & fees
21 Jan - 22 Jan 2026
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
William
The price is ฿5,292
฿5,980 total
includes taxes & fees
5 Jan - 6 Jan 2026
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
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.
Photo by Michael Gibson
Open Photo by Michael Gibson
More cheap stays in Upperville
Baymont by Wyndham Warrenton
7379 Comfort Inn Drive Warrenton VA
The price is ฿1,935 per night from 4 Jan to 5 Jan
฿1,935
฿2,077 total
4 Jan - 5 Jan 2026
includes taxes & fees
6.4/10 (1,003 reviews)
