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Featured Winchester Family Hotels
Baymont by Wyndham Winchester
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. ...
Hampton Inn Winchester
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 ...
Best Western Winchester Hotel
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 ...
Red Roof Winchester - Lexington East
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 Lykins Park and Bluegrass Heritage Museum are ...
Comfort Inn
5250 Revilo Rd, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Community Park and Wiseman ...
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
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! (660 reviews)
"I booked for the pool and the heater was not working so it was too cold to use comfortably"
Reviewed on Apr 10, 2025
Best Western Winchester Hotel
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! (902 reviews)
"Room was clean and just as expected"
Reviewed on Apr 14, 2025
Comfort Inn
5250 Revilo Rd, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Community Park and Wiseman ...
6.8/10 (325 reviews)
"One night stay to visit Claireborne farm. Comfortable, quiet , clean had everything we needed."
Reviewed on May 5, 2024
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
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 ...
Comfort Inn
5250 Revilo Rd, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Community Park and Wiseman ...
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 by Star Rating
Top Points of Interests in Winchester
- Hotels near Cassell Creek Golf Course
- Hotels near Bluegrass Heritage Museum
- Hotels near Clark Regional Medical Center
- Hotels near Southwind Golf Course
- Hotels near Lykins Park
- Hotels near Community Park
- Hotels near Red River Gorge
- Hotels near Kentucky Horse Park
- Hotels near University of Kentucky
- Hotels near Keeneland Racing Course
- Hotels near Natural Bridge State Park
- Hotels near The Red Mile Racetrack
- Hotels near Kroger Field
- Hotels near Rupp Arena
- Hotels near The Kentucky Castle
- Hotels near Red River Gorge Geological Area
- Hotels near Fayette Mall
Cities near Winchester
- Georgetown Hotels (25.59 mi)
- Richmond Hotels (17.86 mi)
- Stanton Hotels (20.15 mi)
- Slade Hotels (29.2 mi)
- Berea Hotels (29.78 mi)
- Versailles Hotels (30.24 mi)
- Pine Ridge Hotels (34.57 mi)
- Campton Hotels (38.73 mi)
- Nicholasville Hotels (22.72 mi)
- Mount Sterling Hotels (13.65 mi)
- Appalachian Mountains Hotels (265.2 mi)
- Paris Hotels (15.69 mi)
- Northern Kentucky Hotels (17.79 mi)
- Beattyville Hotels (38.73 mi)
- Daniel Boone National Forest Hotels (41.98 mi)
- Lancaster Hotels (33.57 mi)
- Frenchburg Hotels (30.27 mi)
- Wilmore Hotels (27.7 mi)
- Cynthiana Hotels (28.33 mi)
- Irvine Hotels (22.92 mi)
Car Rentals Near Winchester
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- Car rentals in Paris
- Car rentals in Northern Kentucky
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- Car rentals in Daniel Boone National Forest
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Top Family Hotel Destinations
- Las Vegas Family Hotels
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- Miami Beach Family Hotels
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Top Booked Hotels in Winchester
- Baymont by Wyndham Winchester
- Quality Inn Lexington -Horse Park
- GuestHouse Lexington
- Marriott Lexington Griffin Gate Golf Resort & Spa
- GLō Best Western Lexington
- Embassy Suites by Hilton Lexington/UK Coldstream
- Hyatt Regency Lexington
- Holiday Inn Lexington - Hamburg by IHG
- Hilton Lexington/Downtown
- Elwood Hotel & Suites
- The Campbell House Lexington, Curio Collection by Hilton