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Featured Winchester Hotels with a Pool

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. ...

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 ...

Comfort Inn Winchester
5250 Revilo Rd Winchester KY
Fully refundable
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Community Park and Wiseman ...

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 ...
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
Cities near Winchester
- Richmond Hotels (17.86 mi)
- Georgetown Hotels (25.59 mi)
- Versailles Hotels (30.24 mi)
- Slade Hotels (29.2 mi)
- Berea Hotels (29.78 mi)
- Stanton Hotels (20.15 mi)
- Appalachian Mountains Hotels (394.78 mi)
- Campton Hotels (38.73 mi)
- Nicholasville Hotels (22.72 mi)
- Mount Sterling Hotels (13.65 mi)
- Pine Ridge Hotels (34.57 mi)
- Beattyville Hotels (38.73 mi)
- Paris Hotels (15.69 mi)
- Northern Kentucky Hotels (17.79 mi)
- Lancaster Hotels (33.57 mi)
- Frenchburg Hotels (30.27 mi)
- Daniel Boone National Forest Hotels (41.98 mi)
- Wilmore Hotels (27.7 mi)
- Cynthiana Hotels (28.33 mi)
- Irvine Hotels (22.92 mi)
Most Booked Hotels in Winchester
- Comfort Inn Winchester
- Quality Inn Lexington -Horse Park
- GuestHouse Lexington
- 21c Museum Hotel Lexington
- Marriott Lexington Griffin Gate Golf Resort & Spa
- Origin Lexington a Wyndham Hotel
- Embassy Suites by Hilton Lexington/UK Coldstream
- Fairfield Inn & Suites by Marriott Lexington North
- Motel 6 Lexington I-75 Hamburg
- Elwood Hotel & Suites
- Hilton Lexington/Downtown
- Hyatt Regency Lexington
- Holiday Inn Express Lexington - Horse Park Area by IHG
