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Hotels in Winchester

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Choose from 1187 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! (1,000 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
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
  • 36 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 pool in ...
8.6/10 Excellent! (276 reviews)
La habitación y el personal muy amable.

Reviewed on Dec 15, 2025

Spark by Hilton Lexington Hamburg
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! (1,006 reviews)
Didnt eat breakfast. Staff at BBM were awesome. Rooms temp was not able to be managed…warm.

Reviewed on Dec 14, 2025

Hilton Lexington/Downtown
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! (1,084 reviews)
Yes

Reviewed on Dec 15, 2025

The Manchester
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
  • 37 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 ...
8.2/10 Very Good! (1,502 reviews)
Efficient. Convenient location.

Reviewed on Dec 15, 2025

GuestHouse Lexington
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
  • 41 min drive from Clark Regional Medical Center
Stay at this hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (1,005 reviews)
Great stay

Reviewed on Dec 8, 2025

DoubleTree Suites by Hilton Hotel Lexington
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! (802 reviews)
Friendly helpful front desk staff, Clean rooms and the Lobby decorated like Whoville is awesome.

Reviewed on Dec 11, 2025

Candlewood Suites Lexington Medical District by IHG
Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

2 out of 5
750 Newtown Court Lexington KY
  • 49 min drive from Clark Regional Medical Center
Stay at this motel in Lexington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
5.6/10 (1,003 reviews)
Great place to stay.

Reviewed on Dec 3, 2025

Motel 6 Lexington, KY - Airport
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! (1,000 reviews)
A little pricy but good otherwise

Reviewed on Dec 7, 2025

Hyatt Regency Lexington
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
Stay at this hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
9.2/10 Wonderful! (2,273 reviews)
It appears the hotel is not completely finished being built

Reviewed on Dec 9, 2025

GLō Best Western Lexington
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! (1,231 reviews)
All was great!

Reviewed on Dec 10, 2025

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! (492 reviews)
Great staff, a nice social hour time, good hot breakfast, comfortable bed and quiet hotel. Glad we chose to stay here

Reviewed on Dec 10, 2025

Staybridge Suites Lexington S Medical Ctr Area by IHG
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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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 1,187 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 $60. 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?

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How many hotels are there in Winchester?

With over 1,187 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 $60.

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