A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Family friendly Hotels in Winchester, Virginia

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Check availability on Winchester Family friendly Hotels

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

Our top choices for Winchester family-friendly hotels

Front of property - evening/night

Skyland

Skyland
2.0 star property
Luray
8.8 out of 10, Excellent, (1,003 reviews)
The price is P11,303
P13,462 total
includes taxes & fees
Jul 28 - Jul 29
Skyland
Lobby

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,003 reviews)
The price is P4,239
P4,718 total
includes taxes & fees
Jul 7 - Jul 8
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Blackout drapes, iron/ironing board, free cribs/infant beds

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,004 reviews)
  • cleanliness
    Splash into family fun at this Winchester hotel with seasonal outdoor pool, breakfast, and kid-friendly accommodations.
The price is P5,691
P6,334 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn Winchester
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, (1,007 reviews)
  • cleanliness
    Child-friendly indoor pool and activities make this hotel a perfect Winchester family retreat with premium entertainment extras.
The price is P5,651
P6,475 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Winchester Se-Historic Gateway by IHG
Restaurant

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, (906 reviews)
The price is P6,750
P7,647 total
includes taxes & fees
Aug 2 - Aug 3
Hampton Inn Winchester N/Conference Center, VA
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, (1,002 reviews)
  • cleanliness
    Family-friendly fun at this Winchester inn begins with an indoor pool, complimentary breakfast, and premium entertainment options.
The price is P5,750
P6,399 total
includes taxes & fees
Jul 27 - Jul 28
Country Inn & Suites by Radisson, Winchester, VA
Lobby

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,429 reviews)
  • cleanliness
    A kid-friendly getaway with indoor pool and free breakfast, just minutes from the Shenandoah Valley Discovery Museum.
The price is P5,651
P6,290 total
includes taxes & fees
Jul 26 - Jul 27
Microtel Inn & Suites by Wyndham Winchester
Lobby

Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,001 reviews)
The price is P6,093
P6,842 total
includes taxes & fees
Jul 12 - Jul 13
Comfort Inn Woodstock Shenandoah
Free daily on-the-go breakfast

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
2.0 star property
Winchester
6.6 out of 10, (535 reviews)
  • cleanliness
    Friendly Winchester escape where kids enjoy complimentary breakfast and convenient amenities near family attractions.
The price is P3,594
P4,000 total
includes taxes & fees
Jul 7 - Jul 8
Days Inn by Wyndham Winchester
Lobby

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Outdoor adventures and kid-friendly comforts await near historic Harpers Ferry with premium TV, cribs, and nature trails.
The price is P5,631
P6,307 total
includes taxes & fees
Jul 29 - Jul 30
Quality Inn Harpers Ferry - Charles Town
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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Choose what matters most at family-friendly hotels in Winchester

Breakfast included
Pool

Family-friendly hotels with free breakfast in Winchester

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, (1007)
The price is P5,651
P6,475 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Winchester Se-Historic Gateway by IHG
View all properties

Family-friendly hotels with pools in Winchester

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, (1007)
The price is P5,651
P6,475 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Winchester Se-Historic Gateway 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.
View all properties

Top Winchester Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

8/10 Good
"Room was nicely appointed."
Kimberly 1-night trip
Posted 8 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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?
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 choices for your stay with the kids include Microtel Inn & Suites by Wyndham Winchester and Quality Inn Winchester.
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, Winchester Little Theater, and Apple Blossom Mall. Make sure you have lots of time for activities like Handley Regional Library and Apple Valley Square Shopping Center.

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