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Hotels in Winchester

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Last Minute Hot Rate® Hotel Deals in Winchester

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Choose from 595 Winchester Hotel Deals

Red Roof Inn Lexington - Winchester
Red Roof Inn Lexington - Winchester
2 out of 5
1100 Interstate Drive, Winchester, KY, 40391
  • 4 min drive from Bluegrass Heritage Museum
The price is $71 per night from May 24 to May 25
Stay at this business-friendly motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the WiFi in ...
Red Roof Inn Lexington - Winchester
Hampton Inn Winchester
Hampton Inn Winchester
2.5 out of 5
1025 Early Dr, Winchester, KY, 40391
  • 29 min walk from Bluegrass Heritage Museum
The price is $125 per night from May 30 to May 31
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 rooms ...
Hampton Inn Winchester
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY, 40391
  • 29 min walk from Bluegrass Heritage Museum
The price is $79 per night from May 29 to May 30
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the overall value ...
Baymont by Wyndham Winchester
Best Western Winchester Hotel
Best Western Winchester Hotel
2.5 out of 5
1307 W Lexington Ave, Winchester, KY, 40391
  • 4 min drive from Bluegrass Heritage Museum
The price is $85 per night from May 30 to May 31
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the bar in our reviews. ...
Best Western Winchester Hotel
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
2.5 out of 5
100 Winchester Plaza, Winchester, KY, 40391
  • 6 min drive from Bluegrass Heritage Museum
The price is $121 per night from Jun 19 to Jun 20
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
Comfort Inn
Comfort Inn
2.5 out of 5
5250 Revilo Rd, Winchester, KY, 40391
  • 6 min drive from Bluegrass Heritage Museum
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our ...
Comfort Inn
GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY, 40511
  • 51 min drive from Bluegrass Heritage Museum
The price is $110 per night from May 24 to May 25
Stay at this 3-star hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the overall value in our reviews. ...
GLō Best Western Lexington
Hyatt Place Lexington
Hyatt Place Lexington
3 out of 5
2001 Bryant Rd, Lexington, KY, 40509
  • 37 min drive from Bluegrass Heritage Museum
The price is $105 per night from May 24 to May 25
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hyatt Place Lexington
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
2.5 out of 5
100 Canebrake Drive, Lexington, KY, 40509
  • 33 min drive from Bluegrass Heritage Museum
The price is $110 per night from May 24 to May 25
Stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY, 40511
  • 52 min drive from Bluegrass Heritage Museum
The price is $122 per night from May 30 to May 31
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful staff ...
Embassy Suites by Hilton Lexington/UK Coldstream
Natural Bridge State Resort Park
Natural Bridge State Resort Park
3.5 out of 5
2135 Natural Bridge Road, Slade, KY, 40376
  • 1 hour drive from Bluegrass Heritage Museum
The price is $105 per night from May 24 to May 25
Stay at this 3.5-star cabin in Slade. Enjoy free WiFi, free parking, and breakfast. Our guests praise the WiFi and the helpful staff in our reviews. Popular ...
Natural Bridge State Resort Park
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY, 40505
  • 40 min drive from Bluegrass Heritage Museum
The price is $71 per night from May 24 to May 25
Stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
GuestHouse Lexington
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Winchester

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Winchester hotel with Hotwire to complete your one-of-a-kind travel checklist.

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 595 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 $49. 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 up to 60% 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 save up to 60% off 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 $49.

How many hotels are there in Winchester?

With over 595 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 $49.

How to find cheap car rentals in Winchester?

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 even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Winchester now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Winchester right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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