Search for Cheap Deals on
Hotels in Winchester

Photo by Hyelsinta

Check Last Minute Winchester Hotel Deals

Tonight Jun 27 - Jun 28This weekend Jun 27 - Jun 29

Choose from 1139 Winchester Hotel Deals

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
  • 29 min walk from Bluegrass Heritage Museum
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. ...
7/10 Good! (706 reviews)
"Very nice hotel. Staff was wonderful."

Reviewed on Jun 25, 2025

Baymont by Wyndham Winchester
DoubleTree Suites by Hilton Hotel Lexington
DoubleTree Suites by Hilton Hotel Lexington
4 out of 5
2601 Richmond Rd, Lexington, KY
  • 44 min drive from Bluegrass Heritage Museum
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,012 reviews)
"The outdoor pool was too close to the dumpster. The room is nice but the AC unit is way loud. Parking was plenty and easy. Most guests were supper friendly and courteous. Some guests on the same floor we stayed on Friday were inconsiderate and constantly entering and leaving and knocking and slamming ..."

Reviewed on Jun 24, 2025

DoubleTree Suites by Hilton Hotel 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
  • 52 min drive from Bluegrass Heritage Museum
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 ...
8.6/10 Excellent! (1,010 reviews)
Good place for a night or two
"Good place, it is just getting old without having any updates. It had peeling paint, old carpet, things like that. Good place to stay for a night or two. Rooms were clean and comfortable."

Reviewed on Jun 24, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
  • 55 min drive from Bluegrass Heritage Museum
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! (1,006 reviews)
Love this place!
"I adore this hotel. I already knew I loved the restaurant and having the opportunity to spend the night confirmed what I suspected. The rooms are great, too!"

Reviewed on Jun 26, 2025

Elwood Hotel & Suites
Fairfield Inn & Suites by Marriott Lexington North
Fairfield Inn & Suites by Marriott Lexington North
3 out of 5
2100 Hackney Pl, Lexington, KY
  • 51 min drive from Bluegrass Heritage Museum
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,007 reviews)
"Only thing was arriving at 9 pm there was no parking spots left"

Reviewed on Jun 25, 2025

Fairfield Inn & Suites by Marriott Lexington North
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
  • 54 min drive from Bluegrass Heritage Museum
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! (890 reviews)
"Very friendly staff, from check in to bar/restaurant to valets. That's not an accident. And the place is beautfiful, tidy and a little quirky. Would definitely stay again."

Reviewed on Jun 24, 2025

The Manchester
Quality Inn Lexington -Horse Park
Quality Inn Lexington -Horse Park
2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
  • 51 min drive from Bluegrass Heritage Museum
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! (1,623 reviews)
"Ice machine were all broken. Luggage carts were broken too. Room was clean & quiet."

Reviewed on Jun 24, 2025

Quality Inn Lexington -Horse Park
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
  • 40 min drive from Bluegrass Heritage Museum
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! (1,219 reviews)
"Clean, convenient. Quick breakfast, staff friendly and helpful"

Reviewed on Jun 23, 2025

GuestHouse Lexington
Spark by Hilton Lexington Hamburg
Spark by Hilton Lexington Hamburg
2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
  • 40 min drive from Bluegrass Heritage Museum
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 pool in ...
8.8/10 Excellent! (29 reviews)
"Great people great location very clean"

Reviewed on Jun 23, 2025

Spark by Hilton Lexington Hamburg
Marriott Lexington Griffin Gate Golf Resort & Spa
Marriott Lexington Griffin Gate Golf Resort & Spa
4.5 out of 5
1800 Newtown Pike, Lexington, KY
  • 51 min drive from Bluegrass Heritage Museum
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! (456 reviews)
"Great place."

Reviewed on Jun 25, 2025

Marriott Lexington Griffin Gate Golf Resort & Spa
Tru by Hilton University Medical Center
Tru by Hilton University Medical Center
2.5 out of 5
535 Waller Avenue, Lexington, KY
  • 55 min drive from Bluegrass Heritage Museum
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (359 reviews)
"It was clean and comfortable. The bathrooms were nice. The shower was a pleasant surprise as were the pillows."

Reviewed on Jun 24, 2025

Tru by Hilton University Medical Center
Hyatt Place Lexington
Hyatt Place Lexington
3 out of 5
2001 Bryant Rd, Lexington, KY
  • 37 min drive from Bluegrass Heritage Museum
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
Nice hotel, but ..
"Service was great. We had a problem with the first room (air conditioning rattle) & we were quickly given another room. However, you might ask to be in odd number room because the traffic from the highway was loud and disturbed our sleep."

Reviewed on Jun 25, 2025

Hyatt Place 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.

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 1,139 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 . 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 .

How many hotels are there in Winchester?

With over 1,139 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 .

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.