Search for Cheap Deals onHotels in Winchester
Choose from 1148 Winchester Hotel Deals

Baymont by Wyndham Winchester
Reviewed on Jul 17, 2025

Value Stay
Reviewed on Jul 13, 2025

Spark by Hilton Lexington Hamburg
Reviewed on Jul 19, 2025

Hilton Lexington/Downtown
Reviewed on Jul 12, 2025

GuestHouse Lexington
Reviewed on Jul 16, 2025

Quality Inn Lexington -Horse Park
Reviewed on Jul 16, 2025

Elwood Hotel & Suites
Reviewed on Jul 16, 2025

Fairfield Inn & Suites by Marriott Lexington North
Reviewed on Jul 16, 2025

Hyatt Place Lexington
Reviewed on Jul 16, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
Reviewed on Jul 14, 2025

The Manchester
Reviewed on Jul 16, 2025

Days Inn Lexington SE/Hamburg
Reviewed on Jul 16, 2025
Find cheap hotels in Winchester
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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Winchester.
Choosing the right hotel in Kentucky has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Winchester’s 1,148 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $64. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Winchester hotel deals at the last minute.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Winchester. No matter your reason for visiting Winchester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Winchester hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Winchester for as low as $64.
How many hotels are there in Winchester?
With over 1,148 hotels in Winchester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $64.
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Finding a cheap car rental deal in Winchester is as easy as scoring cheap hotels in Winchester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.
Top Booked Hotels in Winchester
- Baymont by Wyndham Winchester
- Spark by Hilton Lexington Hamburg
- Hilton Lexington/Downtown
- GuestHouse Lexington
- Quality Inn Lexington -Horse Park
- Elwood Hotel & Suites
- Fairfield Inn & Suites by Marriott Lexington North
- Hyatt Place Lexington
- Embassy Suites by Hilton Lexington/UK Coldstream
- Days Inn Lexington SE/Hamburg
- GLō Best Western Lexington
- The Campbell House Lexington, Curio Collection by Hilton
- Hotels near Clark Regional Medical Center
- Hotels near Bluegrass Heritage Museum
- Hotels near Southwind Golf Course
- Hotels near Lykins Park
- Hotels near Cassell Creek Golf Course
- 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 Kroger Field
- Hotels near Rupp Arena
- Hotels near Natural Bridge State Park
- Hotels near Red River Gorge Geological Area
- Hotels near The Red Mile Racetrack
- Georgetown Hotels
- Richmond Hotels
- Berea Hotels
- Slade Hotels
- Versailles Hotels
- Stanton Hotels
- Appalachian Mountains Hotels
- Pine Ridge Hotels
- Mount Sterling Hotels
- Nicholasville Hotels
- Campton Hotels
- Northern Kentucky Hotels
- Paris Hotels
- Beattyville Hotels
- Daniel Boone National Forest Hotels
- Lancaster Hotels
- Cynthiana Hotels
- Frenchburg Hotels
- Wilmore Hotels
- Eastern Kentucky Hotels