Book Kid-Friendly Hotels in Winchester from $69

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

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Winchester Kid Friendly Hotels

Hampton Inn Winchester

Hampton Inn Winchester

1025 Early Dr Winchester KY
$115 nightly
The price is $127 total per night from Mar 30 to Mar 31
$127 total
Mar 30 - Mar 31
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
9.2/10 Wonderful! (457 reviews)
Room was clean and modern.

Reviewed on Mar 1, 2026

Opens in a new windowHampton Inn Winchester
Best Western Winchester Hotel

Best Western Winchester Hotel

1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $89 total per night from Mar 15 to Mar 16
$89 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express ...
8.4/10 Very Good! (1,000 reviews)
The room was really clean. The remote and TV system sucks. It’s ridiculously hard and the remotes are awful. There was no freezer in the fridge, but the people out the front desk were nice enough to keep my ice packs cold in their freezer. Unfortunately my smoke free room was not smoke-free and when ...

Reviewed on Mar 4, 2026

Opens in a new windowBest Western Winchester Hotel
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $79 total per night from Mar 12 to Mar 13
$79 total
Mar 12 - Mar 13
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will ...
7.2/10 Good! (778 reviews)
Bathroom door didn’t close.

Reviewed on Feb 6, 2026

Opens in a new windowBaymont by Wyndham Winchester
Comfort Inn Winchester

Comfort Inn Winchester

5250 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $83 total per night from Mar 30 to Mar 31
$83 total
Mar 30 - Mar 31
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. Free self parking ...
7/10 Good! (357 reviews)
It has a weird foyer that feels shady. The room was survivable and the front there were MANY black shavings on between the sheet layers which the AI (google lens) said were from bugs and possibly bed bugs, there were hairs a 1/4 inch and less, and ‘crumbs’ /black and brown droppings behind the toilet ...

Reviewed on Mar 10, 2026

Opens in a new windowComfort Inn Winchester
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

1100 Interstate Drive Winchester KY
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $69 total per night from Mar 15 to Mar 16
$69 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are ...
6.4/10 (591 reviews)
The room was clean but there was a strong cleaning chemical smell inside that bothered me as I am sensitive to strong scent. They only give 1 small bottle of shampoo and no conditioner. No breakfast either. It’s all good as we only needed one night stay and for that price it’s all good.

Reviewed on Feb 21, 2026

Opens in a new windowRed Roof Inn Winchester - Lexington East
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

Hampton Inn Winchester

Hampton Inn Winchester

1025 Early Dr Winchester KY
$115 nightly
The price is $127 total per night from Mar 30 to Mar 31
$127 total
Mar 30 - Mar 31
Total with taxes and fees
9.2/10 Wonderful! (457 reviews)

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!

Package deals, things to do & more in Winchester

Best flights+hotels package deals to Winchester

Best flights+hotels package deals to WinchesterOpens in a new window

Our top All Inclusive family-friendly hotels in Winchester

Our top All Inclusive family-friendly hotels in WinchesterOpens in a new window

Villas, cabins and more rentals in Winchester

Villas, cabins and more rentals in WinchesterOpens in a new window

Recent Winchester Hotel Reviews By Fellow Wanderers

Elwood Hotel & Suites

Elwood Hotel & Suites

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Friendly staff that got us checked in early. Our room was cleaned and organized while we were out exploring the city. The restaurant had amazing food and the ordering process was quick and easy. I would highly recommend coming here instead of the big name hotels. "
A verified traveler stayed at Elwood Hotel & Suites
Elwood Hotel & Suites

Explore More Ways to Travel with Travelocity