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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
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. 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! (677 reviews)
"The staff was great."
Reviewed on May 12, 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 ...
8.2/10 Very Good! (908 reviews)
"Rooms clean and spacious; quick hot water; hvac didn’t wake me up at night; breakfast bar was very good, varied selections. Minuses would be parking a little tight and didn’t see any security cameras"
Reviewed on May 8, 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 (326 reviews)
"Didn’t stay last night"
Reviewed on May 12, 2025
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 Bluegrass Heritage Museum
- Hotels near Clark Regional Medical Center
- Hotels near Cassell Creek Golf Course
- Hotels near Lykins Park
- Hotels near Southwind Golf Course
- Hotels near Community Park
- Hotels near Red River Gorge
- Hotels near Kentucky Horse Park
- Hotels near University of Kentucky
- Hotels near The Red Mile Racetrack
- Hotels near Natural Bridge State Park
- Hotels near Keeneland Racing Course
- Hotels near Rupp Arena
- Hotels near Kroger Field
- Hotels near The Kentucky Castle
- Hotels near Red River Gorge Geological Area
- Hotels near University of Kentucky Albert B. Chandler Hospital
- 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)
- Nicholasville Hotels (22.72 mi)
- Pine Ridge Hotels (34.57 mi)
- Mount Sterling Hotels (13.65 mi)
- Campton Hotels (38.73 mi)
- Appalachian Mountains Hotels (265.2 mi)
- Paris Hotels (15.69 mi)
- Northern Kentucky Hotels (17.79 mi)
- Beattyville Hotels (38.73 mi)
- Lancaster Hotels (33.57 mi)
- Wilmore Hotels (27.7 mi)
- Daniel Boone National Forest Hotels (41.98 mi)
- Cynthiana Hotels (28.33 mi)
- Frenchburg Hotels (30.27 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 Lancaster
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Top Family Hotel Destinations
- Las Vegas Family Hotels
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- Branson Family Hotels
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- Ocean City Family Hotels
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- Reno Family Hotels
- Colorado Springs Family Hotels
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- Niagara Falls Family Hotels
- New York Family Hotels
- Whistler Family Hotels
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- Fort Walton Beach Family Hotels
- Pensacola Beach Family Hotels
- Tampa Family Hotels
- Myrtle Beach Family Hotels
- Miami Beach Family Hotels
- Birmingham Family Hotels
Top Booked Hotels in Winchester
- Quality Inn Lexington -Horse Park
- GLō Best Western Lexington
- GuestHouse Lexington
- Embassy Suites by Hilton Lexington/UK Coldstream
- Days Inn Lexington SE/Hamburg
- The Campbell House Lexington, Curio Collection by Hilton
- Elwood Hotel & Suites
- Hilton Lexington/Downtown
- Origin Lexington a Wyndham Hotel
- Hyatt Regency Lexington
- Fairfield Inn & Suites by Marriott Lexington North
- Marriott Lexington Griffin Gate Golf Resort & Spa