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Kid-Friendly Hotels in Winchester

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Featured Winchester Family Hotels

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Baymont by Wyndham Winchester
Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hampton Inn Winchester
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Best Western Winchester Hotel
Red Roof Winchester - Lexington East

Red Roof Winchester - Lexington East

2 out of 5
1100 Interstate Drive, Winchester, KY
Fully refundableReserve now, pay when you stay
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions The Holler and Lykins Park are located ...
Red Roof Winchester - Lexington East
Comfort Inn

Comfort Inn

2.5 out of 5
5250 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Community Park and Wiseman ...
Comfort Inn
See all 1,154 properties in Winchester
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

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
7/10 Good! (756 reviews)
"The room was comfortable. The staff was helpful and accommodating."

Reviewed on Oct 1, 2025

Baymont by Wyndham Winchester
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (982 reviews)
"Yes"

Reviewed on Oct 5, 2025

Best Western Winchester Hotel
Comfort Inn

Comfort Inn

2.5 out of 5
5250 Revilo Rd, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Community Park and Wiseman ...
6.8/10 (343 reviews)
Beyond pleased 😊
"This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips."

Reviewed on Oct 10, 2025

Comfort Inn
See all 1,154 properties in Winchester
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 Connecting Rooms in Winchester

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Best Western Winchester Hotel
Comfort Inn

Comfort Inn

2.5 out of 5
5250 Revilo Rd, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Community Park and Wiseman ...
Comfort Inn
See all 1,154 properties in Winchester
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.