Winchester Hotel Guide - Family Friendly Hotels in Winchester, Virginia

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Our top choices for Winchester family-friendly hotels

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 €73
includes taxes & fees
30 Dec - 31 Dec
Microtel Inn & Suites by Wyndham Winchester

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, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is €76
includes taxes & fees
25 Jan - 26 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA

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)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is €78
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG

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 €59
includes taxes & fees
26 Dec - 27 Dec
Super 8 by Wyndham Front Royal

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 €70
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn Winchester

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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is €91
includes taxes & fees
31 Dec - 1 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is €76
includes taxes & fees
28 Dec - 29 Dec
Wayside Inn

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1002)
"great stay with breakfast too"
United States
James
The price is €56
includes taxes & fees
25 Jan - 26 Jan 2026
Sleep Inn & Suites Winchester near University

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, (849)
"Super friendly reception and perfectly clean room. "
United States
Dwight
The price is €102
includes taxes & fees
5 Jan - 6 Jan 2026
Hampton Inn Winchester N/Conference Center, VA

Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (806)
"Everything was great / thank you!"
United States
Mark
The price is €101
includes taxes & fees
29 Dec - 30 Dec
Holiday Inn Express Hotel & Suites Winchester 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.

Top Winchester Hotel Reviews

Frequently asked questions

What's Winchester like for family-friendly holidays?
The historic destination of Winchester is a good choice if you've been thinking about a trip with your children. The entertainment, soaring skyscrapers and theatres are just a few things that make this an attractive family holiday destination. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city centre.
What's the best family accommodation in Winchester?
Holiday Inn Winchester Se-Historic Gateway by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your stay with the children include Microtel Inn & Suites by Wyndham Winchester and Quality Inn Winchester.
How many family hotels will I be able to find in Winchester?
Expedia has 10 family-friendly hotels and other accommodation options in Winchester.
When's the best time to book a family-friendly holiday in Winchester?
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 2°C. Average annual precipitation for Winchester is 1172 mm.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you and the family may want to explore some interesting spots such as Bright Box Theater, Apple Blossom Mall and Winchester Little Theater. Make sure that you have lots of time for activities such as Winchester Gateway and Rocking S Ranch.