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Check availability on Old Town Winchester Family-Friendly Hotels

Our top choices for Old Town Winchester family-friendly hotels

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, (1375)
"Excellent accommodations"
United States
Loretta
The price is 1.898.640 ₫
2.065.721 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Microtel Inn & Suites by Wyndham 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, (1001)
"Have stayed here multiple times -always good"
United States
Robert
The price is 2.223.518 ₫
2.419.188 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
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, (1002)
"Todo excelente "
Mexico
Anner Javier
The price is 1.845.900 ₫
2.087.450 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (1003)
"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 1.555.830 ₫
1.731.718 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Super 8 by Wyndham Front Royal
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is 2.571.916 ₫
2.915.894 ₫ total
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
Quality Inn Winchester

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 1.993.907 ₫
2.169.370 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Quality Inn Winchester
Snack bar
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (846)
"Super friendly reception and perfectly clean room. "
United States
Dwight
The price is 2.720.042 ₫
3.081.807 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Hampton Inn Winchester N/Conference Center, VA
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, (1001)
"The rooms were clean and the facility seemed safe and well maintained. The room had seen many patches and repairs and had a distinct smell. The indoor pool, “gym” and breakfast were a plus. "
United States
tyshia
The price is 1.800.016 ₫
1.958.418 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites Winchester near University
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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Top Old Town Winchester Hotel Reviews

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Frequently asked questions

What's Old Town Winchester like for family-friendly holidays?
The walkable destination of Old Town Winchester is a great choice if you've been thinking about a holiday with the children. The local tours and cafes are just a couple of things that make this an attractive spot for a family holiday. Take to the air and fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the centre of Old Town Winchester.
What's there to see and do with your family in Old Town Winchester?
While you and your family are staying in Old Town Winchester, you may want to visit some family-friendly attractions such as Bright Box Theater, Handley Regional Library and Apple Blossom Mall. Make sure that you have lots of time for activities such as Dinosaur Land and Barns of Rose Hill.