Find Family Hotels in Winchester, VA

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Check availability on Winchester Family Hotels

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Winchester Family 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 AED 264
AED 288 total
includes taxes & fees
5 Jan - 6 January 2026
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, (1004)
"Have stayed here multiple times -always good"
United States
Robert
The price is AED 313
AED 340 total
includes taxes & fees
4 Jan - 5 January 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

3.0 star property
Winchester
9.0 out of 10, Wonderful, (1005)
"Clean room, nicely furnished."
United States
Marilyn
The price is AED 272
AED 307 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Lobby
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay"
United States
Jaron
The price is AED 278
AED 302 total
includes taxes & fees
15 Dec - 16 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, (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 AED 217
AED 241 total
includes taxes & fees
9 Dec - 10 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

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 AED 358
AED 406 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 star property
Winchester
7.8 out of 10, Good, (1000)
"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 AED 251
AED 273 total
includes taxes & fees
4 Jan - 5 January 2026
Sleep Inn & Suites Winchester near University
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is AED 264
AED 328 total
includes taxes & fees
9 Dec - 10 Dec
Wayside Inn
Porch
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 star property
Winchester
9.0 out of 10, Wonderful, (1002)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is AED 364
AED 413 total
includes taxes & fees
4 Jan - 5 January 2026
Hampton Inn Winchester-University/Mall Area
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, (798)
"Clean room, easy and quick check in."
United States
Jacqueline
The price is AED 382
AED 416 total
includes taxes & fees
15 Dec - 16 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.
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Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 19 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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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 by IHG.
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 Rocking S Ranch.