Photo by Michael Gibson

Upperville Hotels

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Check prices for these dates

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3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

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Top 10 trending Upperville hotels

Exterior
Salamander Resort And Spa

Salamander Resort And Spa

5.0 star property
Middleburg
9.2 out of 10, Wonderful, (371)
"The property is at a close proximity to the downtown area. We were able to walk everywhere. Our room was spacious and immaculate. "
United States
Cedric
The price is €559
includes taxes & fees
17 Dec - 18 Dec
Salamander Resort And Spa
Reception
Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town

2.5 star property
Charles Town
9.4 out of 10, Exceptional, (1017)
"Great stay for a quick day trip to visit family. "
United States
Barbara
The price is €107
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Charles Town
Rooftop terrace
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, (1000)
"Great stay "
United States
Gwinn
The price is €96
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Charles Town by IHG
Indoor pool
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1011)
"Nice convenient hotel. Clean."
United States
Jason
The price is €86
includes taxes & fees
18 Dec - 19 Dec
Clarion Inn Harpers Ferry - Charles Town
Terrace/patio
Hilton Garden Inn Haymarket

Hilton Garden Inn Haymarket

3.0 star property
Haymarket
9.4 out of 10, Exceptional, (248)
"Great place to stay"
United States
Rachel
The price is €123
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Haymarket
2 restaurants, breakfast, lunch, dinner served; American cuisine
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)
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
United States
Jeanette
The price is €123
includes taxes & fees
4 Dec - 5 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Desk, iron/ironing board, free WiFi, bed sheets
Extended Stay America Select Suites Gainesville

Extended Stay America Select Suites Gainesville

2.5 star property
Gainesville
6.2 out of 10, (477)
"Amazing place "
United States
Evelyn
The price is €73
includes taxes & fees
28 Dec - 29 Dec
Extended Stay America Select Suites Gainesville
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (763)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is €74
includes taxes & fees
10 Dec - 11 Dec
TRU By Hilton Winchester
Premium bedding, down duvets, in-room safe, individually decorated
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 €448
includes taxes & fees
9 Dec - 10 Dec
Goodstone Inn & Restaurant
Restaurant
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, (516)
"Staff was courteous….helpful…room was clean and comfortable "
United States
David
The price is €124
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Exterior
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, (2212)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is €87
includes taxes & fees
4 Dec - 5 Dec
La Quinta Inn & Suites by Wyndham Winchester
Terrace/patio
Home2 Suites by Hilton Charles Town

Home2 Suites by Hilton Charles Town

3.0 star property
Charles Town
9.6 out of 10, Exceptional, (798)
"It was very nice, clean, and convenient. Will stay there again "
United States
Melony
The price is €124
includes taxes & fees
17 Dec - 18 Dec
Home2 Suites by Hilton Charles Town
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (507)
"Great hotel"
United States
DONNA D
The price is €93
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Winchester
Lobby
Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket

2.5 star property
Gainesville
8.8 out of 10, Excellent, (983)
"This is our second stay here .Everyone here at this location is always so courteous and pleasant."
United States
Andrea
The price is €82
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn by Hilton Gainesville-Haymarket
Exterior
Hampton Inn Warrenton

Hampton Inn Warrenton

2.5 star property
Warrenton
9.0 out of 10, Wonderful, (138)
"Clean room, attentive staff, great breakfast"
United States
Michelle
The price is €103
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Warrenton
Dining
Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton

2.5 star property
Warrenton
6.4 out of 10, (1001)
"We had a one-night stay. Our room was clean and comfortable and the staff was friendly and welcoming. Would stay again."
United States
Carolyn
The price is €57
includes taxes & fees
11 Dec - 12 Dec
Baymont by Wyndham Warrenton
Exterior
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)
"Clean room, nicely furnished."
United States
Marilyn
The price is €77
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1001)
"Great stay"
United States
Jaron
The price is €71
includes taxes & fees
15 Dec - 16 Dec
Quality Inn Winchester
Free buffet breakfast
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 €74
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Lobby
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 €80
includes taxes & fees
9 Dec - 10 Dec
Spark by Hilton 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

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

10/10 Excellent
"Staff is wonderful "
Lane 6-night trip
Posted 2 days ago
Holiday Inn Express Charles Town by IHG

More cheap stays in Upperville

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA
The price is €64 per night from 7 Dec to 8 Dec
€64
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (1,096 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 traveller data. Two other options for your trip to the area are Travelodge by Wyndham Winchester and Salamander Resort And Spa. See all available top hotels, or vacation rentals in Upperville.
What are some of the best holiday rentals that Upperville has to offer?
Terra Alta - Incredible River Views and Hot Tub!: This holiday home rental outside of Upperville is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all vacation rentals in Upperville.
If I need to cancel my hotel reservation in Upperville, will I receive a refund?
Yes, you'll find most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Upperville.
What are some accommodation options with pools in Upperville?
Hilton Garden Inn Dulles North: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Salamander Resort And Spa and La Quinta Inn & Suites by Wyndham Winchester are a couple of other choices with an on-site pool. View all hotels with pools in Upperville.
What's it like to stay in Upperville?
Visitors can enjoy all that Upperville has to offer, including its restaurants. In Upperville, there are 6 hotels and other accommodation options to choose from. Find out more about Upperville.
What should I see while I'm in Upperville?
A couple of favourite places to visit are Sky Meadows State Park and Upperville Park. You'll also find Delaplane Cellars and RdV Vineyards in the area. Take a look at what more there is to see and do in Expedia's Upperville guide.
What's the weather like in Upperville?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Upperville is 1123 mm.

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