Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Holiday Inn Express & Suites Somerset Central by IHG

$367

per person

Oct 29 - Nov 1

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Lexington (LEX)

Book a stay at this business-friendly hotel in Somerset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Somerset Mall and The Center For Rural Development are located nearby.

😉

Reviewed on Sep 16, 2026

21c Museum Hotel Lexington

$642

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Lexington (LEX)

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. Popular attractions Rupp Arena and Red Mile Racetrack are located nearby.

Would stay in Louisville next time.

Reviewed on Sep 22, 2026

Elwood Hotel & Suites

$650

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Lexington (LEX)

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. Popular attractions Red Mile Racetrack and Kroger Field are located nearby.

The Sire Hotel Lexington, Tapestry Collection by Hilton

$886

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Lexington (LEX)

Stay at this hotel in Lexington. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rupp Arena and Red Mile Racetrack are located nearby.

Holiday Inn Lexington - Hamburg by IHG

$943

per person

Oct 30 - Nov 1

found 19 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Lexington (LEX)

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 clean rooms in our reviews. Popular attractions Kroger Field and Rupp Arena are located nearby.

Very good check in desk person.

Reviewed on Sep 23, 2026

Origin Lexington a Wyndham Hotel

$733

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Lexington (LEX)

Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.

The Kentucky Castle

$1,387

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Lexington (LEX)

Book a stay at this spa hotel in Versailles. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Keeneland Racing Course and The Kentucky Castle are located nearby.

Very unique property and restaurant is delicious as well and portions were definitely more than we expected. The corner tower room we stayed in was impressive. It was definitely worth the side quest stop to stay here as our halfway point to Tennessee. If you’re looking for a unique place to stay I highly recommend.

Reviewed on Sep 19, 2026

The Delegate

$768

per person

Oct 29 - Oct 31

just found

Roundtrip non-stop flight included

Denver (DEN) to Lexington (LEX)

Stay at this hotel in Frankfort. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Buffalo Trace Distillery and Old Governor’s Mansion are located nearby.

We only stayed one night but wish we stayed longer. It was perfect location, nice and clean room. Very friendly and helpful staff.

Reviewed on Sep 23, 2026