Book Kid-Friendly Hotels in Winchester from $74

Name: Holiday Inn Express Winchester South-Stephens City by IHG
Price range: $87 total

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

Top Winchester Kid Friendly Hotels

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Fully refundableReserve now, pay when you stay

$118 nightly

$132 total

Nov 19 - Nov 20

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! (1,003 reviews)

"We were very impressed with the breakfast staff. They were amazing. Very friendly , very courteous, and kept the area well cleaned and supplied. What a wonderful way to start the day. Many thanks. Overall, an outstanding place to stay. Will be back again."

Reviewed on Nov 7, 2026

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd Winchester VA

Fully refundable

$86 nightly

$96 total

Dec 6 - Dec 7

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

$121 nightly

$134 total

Nov 22 - Nov 23

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 ...

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

Fully refundable

$76 nightly

$84 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 ...

Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Fully refundableReserve now, pay when you stay

$67 nightly

$75 total

Nov 15 - Nov 16

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 ...

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

$65 nightly

$74 total

Dec 6 - Dec 7

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 ...

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Fully refundableReserve now, pay when you stay

$130 nightly

$148 total

Nov 19 - Nov 20

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

$78 nightly

$87 total

Dec 11 - Dec 12

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

Twi-Lite Inn

53 West 14th Street Front Royal VA

$75 nightly

$83 total

Dec 6 - Dec 7

Total with taxes and fees

8.2/10 Very Good! (591 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!