Book Kid-Friendly Hotels in Winchester from $75

Name: Red Roof Inn Winchester, VA
Price range: $75 total
Rating: 7.2

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 refundableReserve now, pay when you stay

$76 nightly

$82 total

Jan 6 - Jan 7, 2026

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 ...

9.2/10 Wonderful! (1,001 reviews)

Parking was easy, right off the highway The room was immaculate, nothing dirty at all. Did not have the breakfast

Reviewed on Dec 25, 2025

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Fully refundableReserve now, pay when you stay

$127 nightly

$143 total

Jan 6 - Jan 7, 2026

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, ...

9.2/10 Wonderful! (1,009 reviews)

I love this hotel. I have stayed here once or twice a year over the past few years for the affordability, cleanliness, pool, hot tub, and location on my way up north. This past stay I noticed they are doing their best to keep up with increasing maintenance demands and decreasing profits.

Reviewed on Dec 29, 2025

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Fully refundableReserve now, pay when you stay

$114 nightly

$127 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...

9/10 Wonderful! (1,001 reviews)

All great

Reviewed on Dec 11, 2025

Fairfield Inn & Suites Strasburg Shenandoah Valley

33760 Old Valley Pike Strasburg VA

Fully refundableReserve now, pay when you stay

$113 nightly

$126 total

Jan 4 - Jan 5, 2026

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! (1,001 reviews)

Yes

Reviewed on Dec 23, 2025

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

$77 nightly

$87 total

Jan 25 - Jan 26, 2026

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 ...

8.8/10 Excellent! (1,002 reviews)

Hotel was clean but rooms weren’t very soundproof- heard baby crying from a room close, and heavy walking for quite a while at midnight in the room over us.

Reviewed on Dec 26, 2025

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd Winchester VA

Fully refundable

$82 nightly

$89 total

Jan 25 - Jan 26, 2026

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 ...

8.6/10 Excellent! (1,002 reviews)

Nice staff. Helpful.

Reviewed on Dec 23, 2025

Holiday Inn Express Winchester South-Stephens City by IHG

165 Town Run Ln Stephens City VA

Fully refundable

$74 nightly

$81 total

Jan 4 - Jan 5, 2026

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. ...

8.2/10 Very Good! (807 reviews)

Clean lobby, wonderful check in staff, quiet and comfortable room.

Reviewed on Dec 23, 2025

Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Fully refundableReserve now, pay when you stay

$68 nightly

$75 total

Jan 1 - Jan 2, 2026

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 ...

7.2/10 Good! (1,001 reviews)

Just what you expect from Red Roof Inn. Things are a little beat up, but most things work and you get a place to stay with no bugs, and no pet fee

Reviewed on Nov 20, 2025

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

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$127 nightly

$143 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

9.2/10 Wonderful! (1,009 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!