Photo by Michael Gibson

Compare and book 2 Star hotels in Upperville, Virginia

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Our top choices for Upperville 2-star hotels

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1085)
"Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. "
United States
Stefanie
The price is 1.789.488 ₫
1.946.858 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Travelodge by Wyndham Winchester

Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton
2.5 star property
Warrenton
6.4 out of 10, (1001)
"Staff was the friendliest I’ve seen in a long time "
United States
Arden
The price is 1.621.592 ₫
1.739.969 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Baymont by Wyndham Warrenton

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1091)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is 2.539.098 ₫
2.762.539 ₫ total
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn & Suites Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1400)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is 2.084.227 ₫
2.267.640 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Microtel Inn & Suites by Wyndham Winchester

Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA
2.0 star property
Leesburg
8.6 out of 10, Excellent, (1000)
"Great place enjoyed our stay here"
Australia
Marie
The price is 2.107.291 ₫
2.423.385 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Red Roof Inn Leesburg, VA

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is 2.675.811 ₫
3.031.694 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester-University/Mall Area

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 2.805.286 ₫
3.141.920 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Charles Town

Clarion Hotel & Conference Center Leesburg

Clarion Hotel & Conference Center Leesburg
2.5 star property
Leesburg
6.6 out of 10, (1000)
"The rooms and whole facility was immaculately clean. Upon check in the gentleman was extremely nice and helpful Everyone was Awesome from the desk clerk to the cleaning staff! I would definitely recommend if anywhere near this hotel!!10/10"
United States
Lonnie
The price is 2.273.702 ₫
2.614.757 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Clarion Hotel & Conference Center Leesburg

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 2.613.968 ₫
2.979.921 ₫ total
includes taxes & fees
18 Jan - 19 Jan 2026
Hampton Inn by Hilton Gainesville-Haymarket

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)
"Nice place to stay "
United States
Wendy
The price is 2.605.284 ₫
2.943.971 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Charles Town by IHG

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 2.818.444 ₫
3.066.468 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
SpringHill Suites by Marriott Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (772)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is 2.567.915 ₫
2.793.891 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
TRU By Hilton Winchester

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center
2.5 star property
Leesburg
8.0 out of 10, Very good, (1000)
"Hotel is great, clean and quiet"
United States
Chris
The price is 2.062.244 ₫
2.371.580 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Best Western Leesburg Hotel & Conference Center

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)
"Rooms were clean, staffs were friendly and the breakfast was good."
United States
Mouleeswaran
The price is 2.348.703 ₫
2.630.549 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Clarion Inn Harpers Ferry - Charles Town

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very good, (1000)
"Very good and convenient budget motel in Winchester, happy to recommend."
United States
Jane
The price is 1.789.225 ₫
2.027.122 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Motel 6 Winchester, VA

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1001)
"Clean, pet friendly and great check in."
United States
Anita Willsie
The price is 1.816.576 ₫
1.976.435 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Red Roof Inn Winchester, VA

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1000)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is 2.999.498 ₫
3.338.441 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn Front Royal

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)
"Nice place to stay"
United States
Cynthia
The price is 1.734.160 ₫
1.959.601 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Charles Town/Harpers Ferry

Hampton Inn & Suites Leesburg

Hampton Inn & Suites Leesburg
2.5 star property
Leesburg
8.6 out of 10, Excellent, (874)
"Excellent customer service and overall wonderful experience."
United States
Natasha
The price is 2.412.710 ₫
2.774.616 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Hampton Inn & Suites Leesburg

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
Front Royal
7.6 out of 10, Good, (1002)
"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 1.631.592 ₫
1.816.067 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Super 8 by Wyndham Front Royal
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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.

Hiking Sky Meadows State Park...
Photo by Michael Gibson
Open Photo by Michael Gibson

Top Upperville Hotel Reviews