Find Family Hotels in Winchester, VA

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Pick from 36 Winchester Family Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1001)
"Friendly staff clean good value for money. Would stay there again"
The price is AED 308
AED 335 total
includes taxes & fees
24 Nov - 25 Nov
Country Inn & Suites by Radisson, Winchester, VA
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Staff was helpful and friendly. Breakfast was good. "
The price is AED 452
AED 503 total
includes taxes & fees
12 Nov - 13 Nov
Fairfield Inn & Suites Strasburg Shenandoah Valley
Quality Inn
2.5 star property
9.0 out of 10, Wonderful, (1001)
"I like the way our room is decorated. Modern taste. Especially the floor - instead of gross carpeting, a clean floor. So much better. "
The price is AED 262
AED 285 total
includes taxes & fees
19 Nov - 20 Nov
Quality Inn
Hampton Inn Front Royal
2.5 star property
8.8 out of 10, Excellent, (1003)
"Very dog friendly ! Clean "
The price is AED 379
AED 422 total
includes taxes & fees
4 Dec - 5 Dec
Hampton Inn Front Royal
Red Roof Inn Winchester, VA
2.0 star property
7.4 out of 10, Good, (1002)
"Nice hotel "
The price is AED 221
AED 241 total
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn Winchester, VA
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Clean and quiet. Comfy beds. Restaurants nearby."
The price is AED 289
AED 328 total
includes taxes & fees
2 Dec - 3 Dec
Spark by Hilton Winchester
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.2 out of 10, Wonderful, (1004)
"Great property "
The price is AED 465
AED 527 total
includes taxes & fees
11 Nov - 12 Nov
The George Washington Hotel, A Wyndham Grand Hotel
Holiday Inn Express Winchester South-Stephens City, an IHG Hotel
2.5 star property
8.2 out of 10, Very Good, (711)
"Nice place to stay. Staff super friendly. "
The price is AED 344
AED 374 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Inn Express Winchester South-Stephens City, an IHG Hotel
Quality Inn Stephens City - Winchester South
2.5 star property
8.0 out of 10, Very Good, (529)
"This was a nice hotel - newly remodeled - nice breakfast - reasonable propice."
The price is AED 270
AED 294 total
includes taxes & fees
24 Nov - 25 Nov
Quality Inn Stephens City - Winchester South
Hotel Strasburg
3.0 star property
7.8 out of 10, Good, (731)
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
Hotel Strasburg
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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Frequently asked questions

What's Winchester like for family-friendly vacations?
The historic destination of Winchester is a good choice if you’ve been thinking about a trip with your kids. The entertainment, soaring skyscrapers, and theaters are just a few things that make this an attractive family vacation spot. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center.
What's the best hotel for a family vacation to Winchester?
Microtel Inn & Suites by Wyndham Winchester is a hotel with an indoor pool and free parking, and it’s a top choice on Expedia for families. Other good choices for your stay with the kids include Country Inn & Suites by Radisson, Winchester, VA and Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel.
How many family-friendly hotels should I expect to find in Winchester?
Expedia has 10 family-friendly hotels and other accommodations in Winchester.
When's the best time to book a family-friendly vacation in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you and the family might want to check out some interesting spots such as Bright Box Theater, Apple Blossom Mall, and Handley Regional Library. Make sure you have lots of time for activities like Winchester Little Theater and Apple Valley Square Shopping Center.