Book Kid-Friendly Hotels in Winchester from $77

Name: Holiday Inn Express Winchester South-Stephens City by IHG
Price range: $95 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

$84 nightly

$94 total

Sep 2 - Sep 3

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! (1,000 reviews)

"We were pleasantly surprised and very pleased with this property. We enjoyed our overnight stay and would definitely stay again. Convenient to I-81, yet surprisingly quiet"

Reviewed on Aug 26, 2026

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Fully refundableReserve now, pay when you stay

$122 nightly

$136 total

Sep 2 - Sep 3

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! (1,024 reviews)

"they gave us room smelled like hamster or rabit.When we asked to change they changed."

Reviewed on Aug 26, 2026

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

$77 nightly

$87 total

Sep 27 - Sep 28

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! (1,002 reviews)

"Great stay! Very clean and the staff was great."

Reviewed on Aug 26, 2026

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd Winchester VA

Fully refundable

$94 nightly

$105 total

Sep 20 - Sep 21

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 ...

Fairfield Inn & Suites Strasburg Shenandoah Valley

33760 Old Valley Pike Strasburg VA

Fully refundableReserve now, pay when you stay

$118 nightly

$131 total

Sep 13 - Sep 14

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 ...

Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Fully refundableReserve now, pay when you stay

$69 nightly

$77 total

Aug 30 - Aug 31

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 ...

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Fully refundableReserve now, pay when you stay

$122 nightly

$138 total

Sep 7 - Sep 8

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this Georgian 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

$85 nightly

$95 total

Sep 27 - Sep 28

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

$77 nightly

$87 total

Sep 27 - Sep 28

Total with taxes and fees

9.2/10 Wonderful! (1,002 reviews)

Hotels with Childcare in Winchester

Celebration Retreat

440 Scenic Overlook Dr Front Royal VA

Get rates

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!