Book Kid-Friendly Hotels in Winchester from $78
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Top Winchester Kid Friendly Hotels
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$122 nightly
The price is $138 total per night from Apr 20 to Apr 21
$138 total
Apr 20 - Apr 21
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, ...
9.4/10 Exceptional! (1,009 reviews)
Great place in the middle of everything. Beautiful rooms.
Reviewed on Apr 11, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $95 total per night from May 10 to May 11
$95 total
May 10 - May 11
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)
Bien très propre
Reviewed on Apr 13, 2026
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 Apr 26 to Apr 27
$126 total
Apr 26 - Apr 27
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 ...
9/10 Wonderful! (1,003 reviews)
Room assigned when we arrived had not been cleaned nor the bed made up. After calling the front desk the clerk examined another room and we stayed there for our three days
Reviewed on Apr 9, 2026
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Apr 28 to Apr 29
$126 total
Apr 28 - Apr 29
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! (1,006 reviews)
Very clean. Very new. Friendly staff. Shower pressure not that great.
Reviewed on Apr 13, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Apr 26 to Apr 27
$107 total
Apr 26 - Apr 27
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 ...
9/10 Wonderful! (1,002 reviews)
Great place. Simple, clean and convenient.
Reviewed on Apr 10, 2026
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Fully refundable
$96 nightly
The price is $104 total per night from May 4 to May 5
$104 total
May 4 - May 5
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! (1,004 reviews)
Hotel was clean. Staff were helpful and kind!
Reviewed on Apr 8, 2026
Holiday Inn Express Winchester South-Stephens City by IHG
165 Town Run Ln Stephens City VA
Fully refundable
$100 nightly
The price is $109 total per night from Apr 19 to Apr 20
$109 total
Apr 19 - Apr 20
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! (844 reviews)
My room was dated… clean but dated.
Reviewed on Apr 10, 2026
Red Roof Inn Winchester, VA
991 Millwood Pike Winchester VA
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $78 total per night from Apr 19 to Apr 20
$78 total
Apr 19 - Apr 20
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! (1,001 reviews)
During a 14-night stay, room was cleaned some days in an apparently random pattern, the hard flooring seemed to only be mopped once during our stat and not at all in the (tiny) bathroom, laundry was likewise hit and miss. Wi-Fi was fine but it was not possible to use the phone in the room for any ...
Reviewed on Mar 24, 2026
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
$122 nightly
The price is $138 total per night from Apr 20 to Apr 21
$138 total
Apr 20 - Apr 21
Total with taxes and fees
9.4/10 Exceptional! (1,009 reviews)
Hotels with Childcare in Winchester
Celebration Retreat
440 Scenic Overlook Dr Front Royal VA
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!
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Recent Winchester Hotel Reviews By Fellow Wanderers
Fairfield Inn & Suites by Marriott Winchester
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Breakfast was amazing! Lots of selection more than normal. Waffles two ways, eggs, 2 types of sausage... The pool was clean and towels were stocked. Room was very clean and in good repair. Staff was friendly and helpful. No issues with bringing in our service dog or having him at breakfast."
A verified traveler stayed at Fairfield Inn & Suites by Marriott Winchester
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