Book Kid-Friendly Hotels in Winchester from $74

Name: Holiday Inn Express Winchester South-Stephens City by IHG
Price range: $91 total

Find & compare hotels, resorts and vacation rentals for the whole family

Top Winchester Kid Friendly Hotels

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

Fully refundable

$78 nightly

$86 total

Nov 22 - Nov 23

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. Free WiFi ...

9.4/10 Exceptional! (1,013 reviews)

"Not the newest hotel but very clean room and staff accommodating"

Reviewed on Nov 2, 2026

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Fully refundableReserve now, pay when you stay

$114 nightly

$127 total

Dec 3 - Dec 4

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference ...

9.2/10 Wonderful! (1,001 reviews)

"My stay here was great. They offer a good breakfast. The rooms are nice and clean. However, housekeeping needs to do a better job at cleaning the window and the mirrors. They definitely left streaks on it. Other than that, it was great."

Reviewed on Nov 1, 2026

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

$65 nightly

$74 total

Nov 22 - Nov 23

Total with taxes and fees

The hotel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Traveling for business? Take advantage of the business ...

9.2/10 Wonderful! (1,008 reviews)

"Very nice hotel with helpful staff, especially Danielle at the front desk."

Reviewed on Nov 2, 2026

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd Winchester VA

Fully refundable

$86 nightly

$95 total

Nov 29 - Nov 30

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...

8.8/10 Excellent! (1,009 reviews)

"Heated indoor pool. Hot breakfast."

Reviewed on Nov 1, 2026

Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Fully refundableReserve now, pay when you stay

$70 nightly

$78 total

Dec 1 - Dec 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Free parking, express check-in, and express check-out are also ...

7.4/10 Good! (1,004 reviews)

"Parking sucked i had to park half way down the parking spaces they should have spaces for the rooms your in"

Reviewed on Nov 2, 2026

Fairfield Inn & Suites Strasburg Shenandoah Valley

33760 Old Valley Pike Strasburg VA

Fully refundableReserve now, pay when you stay

$127 nightly

$142 total

Nov 15 - Nov 16

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$130 nightly

$148 total

Nov 9 - Nov 10

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...

Holiday Inn Express Winchester South-Stephens City by IHG

165 Town Run Ln Stephens City VA

Fully refundable

$82 nightly

$91 total

Nov 7 - Nov 8

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...

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.

Hotels With Pools in Winchester

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

$65 nightly

$74 total

Nov 22 - Nov 23

Total with taxes and fees

9.2/10 Wonderful! (1,008 reviews)

Hotels with Childcare in Winchester

Celebration Retreat

440 Scenic Overlook Dr Front Royal VA

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Winchester Kid-Friendly Hotels

It’s not a family vacation if you can’t bring the entire clan with you, is it? Next time you have a few days off from work, plan a family-friendly getaway. Set off on an adventure the entire family will love, and book your stay at one of the kid-friendly hotels in Winchester.

Your little ones are the most important thing in your life, so make sure they enjoy your accommodation as much as you do. From a kids-only room service menu (macaroni and cheese, anyone?) to special perks like in-room video game consoles, these lodgings provide a little something extra for the smaller members of your crew. The best family-friendly hotels in Winchester may even offer playgrounds and other activities to keep the kiddos busy. What’s more, some hotels provide a babysitting service so you can get a few hours to yourself!

Whether you’re traveling with one small child or hauling around your entire extended family, Travelocity is here to help. Let us hook you up with hotels for kids in Winchester that will keep your youngsters happy without breaking the bank. You can save even more when you bundle your flight and hotel together, so what are you waiting for? Grab your family and get ready to explore!