Search for Cheap Deals on
Hotels in Winchester

Photo by Hyelsinta

Choose from 1084 Winchester Hotel Deals

Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
  • 49 min drive from Clark Regional Medical Center
The price is $179 per night from Mar 31 to Apr 1
$179
includes taxes & fees
Mar 31 - Apr 1
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (1,008 reviews)
"We didn’t get fresh towels or even our trash emptied. But we paid a lot of $$$ for convenience."

Reviewed on Mar 2, 2025

Hilton Lexington/Downtown
GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
  • 48 min drive from Clark Regional Medical Center
The price is $108 per night from Mar 16 to Mar 17
$108
includes taxes & fees
Mar 16 - Mar 17
Stay at this 3-star hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.2/10 Wonderful! (2,280 reviews)
"Beautiful place to stay."

Reviewed on Mar 2, 2025

GLō Best Western Lexington
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
  • 48 min drive from Clark Regional Medical Center
The price is $100 per night from Mar 16 to Mar 17
$100
includes taxes & fees
Mar 16 - Mar 17
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,013 reviews)
"Very nice, comfortable & relaxing 🤗"

Reviewed on Mar 3, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
Quality Inn Lexington -Horse Park
Quality Inn Lexington -Horse Park
2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
  • 48 min drive from Clark Regional Medical Center
The price is $76 per night from Mar 23 to Mar 24
$76
includes taxes & fees
Mar 23 - Mar 24
Book a stay at this golf hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (1,443 reviews)
Good Value
"This hotel has everything you need. It’s clean and ready upon arrival."

Reviewed on Mar 2, 2025

Quality Inn Lexington -Horse Park
Hyatt Regency Lexington
Hyatt Regency Lexington
3.5 out of 5
401 W High St, Lexington, KY
  • 49 min drive from Clark Regional Medical Center
The price is $163 per night from Mar 17 to Mar 18
$163
includes taxes & fees
Mar 17 - Mar 18
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,002 reviews)
"Great property great staff"

Reviewed on Mar 2, 2025

Hyatt Regency Lexington
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
  • 50 min drive from Clark Regional Medical Center
The price is $219 per night from Mar 23 to Mar 24
$219
includes taxes & fees
Mar 23 - Mar 24
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. ...
9.4/10 Exceptional! (725 reviews)
"Beautiful hotel, easily walkable to Ruppnarena and downtown Lex!!"

Reviewed on Mar 2, 2025

The Manchester
Marriott Lexington Griffin Gate Golf Resort & Spa
Marriott Lexington Griffin Gate Golf Resort & Spa
4.5 out of 5
1800 Newtown Pike, Lexington, KY
  • 48 min drive from Clark Regional Medical Center
The price is $135 per night from Mar 30 to Mar 31
$135
includes taxes & fees
Mar 30 - Mar 31
Stay at this 4.5-star luxury resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (384 reviews)
"Comfortable, clean and quiet. Friendly staff, my number one choice when I’m in the area"

Reviewed on Mar 4, 2025

Marriott Lexington Griffin Gate Golf Resort & Spa
Everhome Suites Lexington - Horse Park
Everhome Suites Lexington - Horse Park
2.5 out of 5
757 Newtown Springs Drive, Lexington, KY
  • 48 min drive from Clark Regional Medical Center
The price is $91 per night from Mar 19 to Mar 20
$91
includes taxes & fees
Mar 19 - Mar 20
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (108 reviews)
"This is a new all suite hotel! The room was immaculately clean and had a fridg, stove top burner, dishwasher, and 55in TV! Only problem for me personally was the internet connection problems which prevented me from casting to the TV. The tv channels offered didn’t have anything I prefer to watch ..."

Reviewed on Mar 2, 2025

Everhome Suites Lexington - Horse Park
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington Hamburg
3 out of 5
1750 PLEASANT RIDGE DR, Lexington, KY
  • 34 min drive from Clark Regional Medical Center
The price is $118 per night from Mar 13 to Mar 14
$118
includes taxes & fees
Mar 13 - Mar 14
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 ...
9.2/10 Wonderful! (732 reviews)
"Very comfortable, clean and roomy"

Reviewed on Mar 2, 2025

Home2 Suites by Hilton Lexington Hamburg
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
  • 37 min drive from Clark Regional Medical Center
The price is $71 per night from Mar 16 to Mar 17
$71
includes taxes & fees
Mar 16 - Mar 17
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,118 reviews)
"The property was very nice and located in a good area of Lexington."

Reviewed on Mar 3, 2025

GuestHouse Lexington
Candlewood Suites Lexington Medical District, an IHG Hotel
Candlewood Suites Lexington Medical District, an IHG Hotel
2.5 out of 5
501 Waller Avenue, Lexington, KY
  • 52 min drive from Clark Regional Medical Center
The price is $107 per night from Mar 9 to Mar 10
$107
includes taxes & fees
Mar 9 - Mar 10
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (536 reviews)
"Awesome place"

Reviewed on Mar 3, 2025

Candlewood Suites Lexington Medical District, an IHG Hotel
Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
  • 52 min drive from Clark Regional Medical Center
The price is $131 per night from Mar 9 to Mar 10
$131
includes taxes & fees
Mar 9 - Mar 10
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our ...
9.2/10 Wonderful! (933 reviews)
"The rooms were huge, the beds were very comfortable and the hotel staff were super friendly! It was a very nice hotel and beautifully decorated! We will definitely stay there again when we go back to Lexington for an overnighter! It is about a 10 minute drive to Rupp Arena."

Reviewed on Mar 2, 2025

Elwood Hotel & Suites
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.

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 1,084 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 $71. 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 $71.

How many hotels are there in Winchester?

With over 1,084 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 $71.

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 unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.