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Hotels in Winchester

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Choose from 1193 Winchester Hotel Deals

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
  • 8 min walk from Clark Regional Medical Center
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 ...
8.4/10 Very Good! (999 reviews)
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.

Reviewed on Dec 14, 2025

Best Western Winchester Hotel
Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr Winchester KY
  • 4 min drive from Clark Regional Medical Center
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 ...
9.2/10 Wonderful! (452 reviews)
Enjoyed our stay.

Reviewed on Dec 6, 2025

Hampton Inn Winchester
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
  • 4 min drive from Clark Regional Medical Center
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! (772 reviews)
Everything was perfect.

Reviewed on Dec 27, 2025

Baymont by Wyndham Winchester
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
  • 50 min drive from Clark Regional Medical Center
Stay at this hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,106 reviews)
Great stay at the Manchester. Beautiful lobby and restaurants and super helpful staff. Despite other reviewers complaining about noise, we found it to be quiet and peaceful (stayed 5 nights). Complimentary coffee was excellent and the many of the food items reasonably priced. A few tweaks might make ...

Reviewed on Dec 31, 2025

The Manchester
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
501 Waller Avenue Lexington KY
  • 52 min drive from Clark Regional Medical Center
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 ...
9.2/10 Wonderful! (832 reviews)
Soooo cozy

Reviewed on Dec 30, 2025

Candlewood Suites Lexington Medical District by IHG
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
  • 31 min drive from Clark Regional Medical Center
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 ...
8.6/10 Excellent! (1,206 reviews)
Absolutely no issues. We enjoyed our stay

Reviewed on Jan 2, 2026

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
209 RUCCIO WAY Lexington KY
  • 53 min drive from Clark Regional Medical Center
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 ...
9.6/10 Exceptional! (524 reviews)
Overall, we enjoyed our stay. HUGE suites! Very quiet. Rooms were very clean. One disappointment - the water pressure in the shower was weak. Also, the bathroom sink cold water "knob" didn't work. It was missing a "screw" to hold into place. I brought it to their attention and they are working on ...

Reviewed on Jan 1, 2026

Staybridge Suites Lexington S Medical Ctr Area by IHG
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
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,004 reviews)
Great location and good workout facility.

Reviewed on Jan 3, 2026

Hyatt Regency Lexington
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
Book a stay at this business-friendly hotel in Lexington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (1,002 reviews)
Clean room nice bedding

Reviewed on Jan 1, 2026

Hilton Lexington/Downtown
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
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,073 reviews)
It was good they are remodeling

Reviewed on Dec 31, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
167 West Main Street Lexington KY
  • 48 min drive from Clark Regional Medical Center
Stay at this hotel in Lexington. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
Clean, comfortable room however, bathroom door was dirty where guests place hands to close it. Artwork in lobby was overly WOKE. Underlying message was not appreciated.

Reviewed on Dec 22, 2025

21c Museum Hotel Lexington
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
  • 52 min drive from Clark Regional Medical Center
Stay at this hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,016 reviews)
Clean room, easy check-in/out, great location for our needs.

Reviewed on Jan 2, 2026

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

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If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $80. 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.

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Frequently Asked Questions About Winchester hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Winchester?

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