Book Kid-Friendly Hotels in Winchester from $76

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Top Winchester Kid Friendly Hotels

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Jul 27 to Jul 28
$144 total
Jul 27 - Jul 28
Total includes 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! (1,002 reviews)
"Hotel was very nice. Service was good and it was clean and convenient."

Reviewed on Jul 14, 2025

The George Washington Hotel, A Wyndham Grand Hotel
Quality Inn

Quality Inn

1601 Martinsburg Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $92 total per night from Jul 30 to Jul 31
$92 total
Jul 30 - Jul 31
Total includes 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 ...
9/10 Wonderful! (1,004 reviews)
"Clean, quiet, and good breakfast options. I’d recommend it"

Reviewed on Jul 21, 2025

Quality Inn
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

33760 Old Valley Pike, Strasburg, VA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Aug 3 to Aug 4
$126 total
Aug 3 - Aug 4
Total includes 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)
"Excellent"

Reviewed on Jul 18, 2025

Fairfield Inn & Suites Strasburg Shenandoah Valley
Hampton Inn Front Royal

Hampton Inn Front Royal

9800 Winchester Rd, Front Royal, VA
$110 nightly
The price is $122 total per night from Aug 14 to Aug 15
$122 total
Aug 14 - Aug 15
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the ...
8.8/10 Excellent! (1,003 reviews)
"Fast check in,clean room,nice breakfast"

Reviewed on Jul 21, 2025

Hampton Inn Front Royal
Spark by Hilton Winchester

Spark by Hilton Winchester

150 Wingate Dr, Winchester, VA
$91 nightly
The price is $103 total per night from Aug 17 to Aug 18
$103 total
Aug 17 - Aug 18
Total includes 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! (1,005 reviews)
"Nice"

Reviewed on Jul 22, 2025

Spark by Hilton Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
$99 nightly
The price is $108 total per night from Jul 27 to Jul 28
$108 total
Jul 27 - Jul 28
Total includes 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! (1,009 reviews)
"."

Reviewed on Jul 21, 2025

Country Inn & Suites by Radisson, Winchester, VA
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

165 Town Run Ln, Stephens City, VA
Fully refundable
$93 nightly
The price is $101 total per night from Jul 27 to Jul 28
$101 total
Jul 27 - Jul 28
Total includes 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! (758 reviews)
"Its so convenient. Right off of 81. The staff is excellent as is the facility."

Reviewed on Jul 15, 2025

Holiday Inn Express Winchester South-Stephens City by IHG
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

991 Millwood Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $76 total per night from Jul 27 to Jul 28
$76 total
Jul 27 - Jul 28
Total includes 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! (1,002 reviews)
Great night stay
"Really friendly staff, room was clean and perfect for our family and dog."

Reviewed on Jul 20, 2025

Red Roof Inn Winchester, VA
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

Hotels with Childcare in Winchester

Celebration Retreat

Celebration Retreat

440 Scenic Overlook Dr, Front Royal, VA

Book a stay at the best kid-friendly hotels in Winchester

How much does it cost to stay in a family hotel in Winchester?


You can book a stay at a kid-friendly resort in Winchester from just $76 per night. Our prices range up $144 per night if you want to enjoy the high life.


How many family-friendly hotels are there in Winchester?


With over 1,998 hotels in Winchester, you have a great selection of kid-friendly places to stay. Whether you’re looking for a cheap-and-cheerful property with plenty of space or an activity-filled kid-friendly resort, there’s a getaway to suit your style and your budget at Travelocity.


What is Travelocity’s cancellation policy for family hotels in Winchester?


We offer free cancellation on select hotels. Policies can vary per property so it's best to check before you book. If you need to amend or cancel your vacation, just visit our Customer Service Portal. 


What are the best kid-friendly hotels in Winchester?


At Travelocity, you can book the best family-friendly Winchester hotel for you and your family by filtering your search by price, property type, and a range of amenities such as breakfast included or free airport shuttle. Use the map to see where the hotels are and the attractions they’re near.


What should I expect in the family-friendly hotels in Winchester?


When you book a kid-friendly Winchester resort, you can expect fun for all the family. Think pools, waterparks, and hot tubs. Think babysitting, kids’ menus, games rooms, and sport facilities—discover your ideal family vacation. Many resorts keep the kids happy, so you can indulge in bars, restaurants, and spas. Check details for each property as offers may vary.


How can I find family hotel deals in Winchester?


Just enter your travel dates and sort your results by price. You can even filter your results by budget, so you’ll only see the deals that are right for your pocket. It’s easy to find great deals on family-friendly hotels in Winchester with Travelocity. 


When is the cheapest time to go to Winchester with your family?


The cheapest time to visit Winchester is usually .


When is the best time to go to Winchester with your kids?


The most popular months are and are great for booking in at a Winchester kid-friendly resort. If you want a quieter vacation—or the kids aren’t in school yet— are usually less busy, but you can find incredible deals all year round with Travelocity. 


Why book a Winchester child-friendly hotel with Travelocity?


Because we search the entire market, so you don’t have to. You’ll find great deals on everything from weekend trips to two-week family vacations. Whatever your budget or your wish list, we’ve got what you’re looking for.


Package deals, things to do & more in Winchester


Recent Winchester Hotel Reviews By Fellow Wanderers

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