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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 1,139 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! (706 reviews)
"Very nice hotel. Staff was wonderful."

Reviewed on Jun 25, 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! (936 reviews)
"best check in staff I have ever experienced. one of the best breakfasts also. Room has a full size jacucci and the pool was open"

Reviewed on Jun 20, 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 (334 reviews)
Perfect Oasis
"We had driven through the night from KC. No sleep. We did a little sightseeing in the area. Our check in time was 3 pm. We were so exhausted. At 1:00 we went in to see if we check in early. The room had just been cleaned. Everything was clean, fresh smelling. The mattress and pillows were perfect ..."

Reviewed on Jun 10, 2025

Comfort Inn
See all 1,139 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 1,139 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.