Search for Cheap Deals onHotels with Pools in Winchester
Photo by Hyelsinta
Check Last Minute Winchester Hotel Deals
You choose what matters — star rating, location, amenities.
We pick the perfect hotel, packed with all your must-haves.
Your hotel is revealed right after booking!
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
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 ...

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
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)
- Pine Ridge Hotels (34.57 mi)
- Nicholasville Hotels (22.72 mi)
- Campton Hotels (38.73 mi)
- Mount Sterling Hotels (13.65 mi)
- Paris Hotels (15.69 mi)
- Appalachian Mountains Hotels (265.2 mi)
- Northern Kentucky Hotels (17.79 mi)
- Beattyville Hotels (38.73 mi)
- Lancaster Hotels (33.57 mi)
- Daniel Boone National Forest Hotels (41.98 mi)
- Wilmore Hotels (27.7 mi)
- Cynthiana Hotels (28.33 mi)
- Frenchburg Hotels (30.27 mi)
- Irvine Hotels (22.92 mi)
Most 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
- Marriott Lexington Griffin Gate Golf Resort & Spa
- Elwood Hotel & Suites
- Hilton Lexington/Downtown
- Hyatt Regency Lexington
- Origin Lexington a Wyndham Hotel
Car Rentals Near Winchester
- Car rentals in Georgetown
- Car rentals in Richmond
- Car rentals in Stanton
- Car rentals in Slade
- Car rentals in Berea
- Car rentals in Versailles
- Car rentals in Pine Ridge
- Car rentals in Nicholasville
- Car rentals in Campton
- Car rentals in Mount Sterling
- Car rentals in Paris
- Car rentals in Appalachian Mountains
- Car rentals in Northern Kentucky
- Car rentals in Beattyville
- Car rentals in Lancaster
- Car rentals in Daniel Boone National Forest
Top Destinations for Hotels with Pools
- Atlantic City Hotels with Pools
- Cleveland Hotels with Pools
- Downtown Chicago Hotels with Pools
- Downtown Omaha Hotels with Pools
- Chicago Hotels with Pools
- Philadelphia Hotels with Pools
- Downtown Milwaukee Hotels with Pools
- New York Hotels with Pools
- Louisville Hotels with Pools
- Downtown Cleveland Hotels with Pools
- Lincoln Hotels with Pools
- Niagara Falls Hotels with Pools
- South Beach Hotels with Pools
- Memphis Hotels with Pools
- Los Angeles Hotels with Pools
- Downtown Indianapolis Hotels with Pools
- Toledo Hotels with Pools
- Lexington Hotels with Pools
- Downtown Minneapolis Hotels with Pools
- Cleveland Hotels with Pools