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Check availability on Winchester Family-Friendly Hotels

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Winchester Family-Friendly Hotels

Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1374)
"Excellent accommodations"
United States
Loretta
The price is 1.898.280 ₫
2.065.329 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Microtel Inn & Suites by Wyndham Winchester
Lobby
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, (1017)
"Have stayed here multiple times -always good"
United States
Robert
The price is 2.231.534 ₫
2.427.909 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Country Inn & Suites by Radisson, Winchester, VA
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, (1007)
"The room was very clean and the staff were friendly and courteous."
United States
Maria
The price is 1.982.648 ₫
2.236.217 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Snack bar
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, (843)
"The hotel was clean, and the staff was friendly. "
United States
Brett
The price is 2.720.868 ₫
3.082.743 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Winchester N/Conference Center, VA
Lobby
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Staff are amazing stayed twice in a week and every one was so kind friendly and happy to have us The women who is in the breakfast room was super The rooms where clean and comfortable "
United States
Koren
The price is 1.994.512 ₫
2.170.029 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn Winchester
Lobby
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)
"Clean rooms friendly staff"
United States
Ken
The price is 1.399.981 ₫
1.558.179 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
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

4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1007)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is 3.134.799 ₫
3.536.779 ₫ total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Property amenity
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, (795)
"Great place to stay!!"
United States
Thomas
The price is 2.509.948 ₫
2.730.824 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Winchester by IHG
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 star property
Winchester
7.8 out of 10, Good, (1007)
"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 1.725.589 ₫
1.877.442 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Sleep Inn & Suites Winchester near University
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 2.517.330 ₫
2.852.134 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn 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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Top Winchester Hotel Reviews

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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.
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 Handley Regional Library. Make sure that you have lots of time for activities such as Winchester Little Theater and Rocking S Ranch.