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Featured Winchester Kid Friendly Hotels

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
$80 nightly
The price is $88 total per night
$88 total
Dec 18 - Dec 19
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Baymont by Wyndham Winchester in Winchester, you'll be within a 5-minute drive of Lykins Park and The Holler.
Pool
Breakfast included
Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr Winchester KY
$109 nightly
The price is $120 total per night
$120 total
Dec 28 - Dec 29
Total with taxes and fees
A stay at Hampton Inn Winchester places you in the heart of Winchester, within a 5-minute drive of The Holler and Clark County Courthouse.
Pool
Breakfast included
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
$72 nightly
The price is $80 total per night
$80 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Best Western Winchester Hotel in Winchester, you'll be within a 5-minute drive of Clark Regional Medical Center and Bluegrass Heritage Museum.
Pool
Breakfast included
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

2 out of 5
1100 Interstate Drive Winchester KY
$62 nightly
The price is $69 total per night
$69 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Winchester, Red Roof Inn Winchester - Lexington East is within a 5-minute drive of The Holler and Clark County Courthouse.
Pet friendly
Parking included
Comfort Inn Winchester

Comfort Inn Winchester

2.5 out of 5
5250 Revilo Rd Winchester KY
$68 nightly
The price is $75 total per night
$75 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Comfort Inn Winchester places you in the heart of Winchester, within a 5-minute drive of Clark County Medical Center and Clark Regional Medical Center.
Pool
Parking included
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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.

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Winchester hotels essential information

Accommodation
1,181 hotels
Lowest Price
$69
Highest Price
$120
Popular hotels
Baymont by Wyndham Winchester, Hampton Inn Winchester, Best Western Winchester Hotel, Red Roof Inn Winchester - Lexington East, Comfort Inn Winchester

Most Recent Winchester Hotel Reviews

Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"Great staff, a nice social hour time, good hot breakfast, comfortable bed and quiet hotel. Glad we chose to stay here"
A verified traveler stayed at Staybridge Suites Lexington S Medical Ctr Area by IHG
Staybridge Suites Lexington S Medical Ctr Area by IHG

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