Search Deals onPrestonsburg Vacation Packages
Prestonsburg Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Richmond
Price was $510, price is now $481 per person
$481
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
Book a stay at this business-friendly motel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E.C. Million Park and Richmond Area Arts Center are located nearby.
21c Museum Hotel Lexington
Price was $673, price is now $621 per person
$621
per person
Dec 25 - Dec 27
found 10 hours 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.
Just disappointed that the restaurant was closed.
Reviewed on Oct 27, 2026
Montgomery Inn BnB
Price was $746, price is now $702 per person
$702
per person
Dec 25 - Dec 27
found 10 hours ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Stay at this B&B in Versailles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Kentucky Castle and Nostalgia Station Toy Train Museum are located nearby.
Origin Lexington a Wyndham Hotel
Price was $707, price is now $674 per person
$674
per person
Dec 25 - Dec 27
found 10 hours 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.
Elwood Hotel & Suites
Price was $650, price is now $626 per person
$626
per person
Dec 25 - Dec 27
found 10 hours 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.
Loved our stay! Top notch service all around. Bar and food = excellent!
Reviewed on Oct 28, 2026
The Aldenberg Hotel
Price was $742, price is now $718 per person
$718
per person
Dec 25 - Dec 27
found 10 hours ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Stay at this hotel in Versailles. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions The Kentucky Castle and Nostalgia Station Toy Train Museum are located nearby.
Staff was extremely kind. Especially loved shuttle service to Keeneland
Reviewed on Oct 19, 2026
Home2 Suites by Hilton Lexington University / Medical Center
Price was $634, price is now $614 per person
$614
per person
Dec 25 - Dec 27
found 10 hours ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kroger Field and Red Mile Racetrack are located nearby.
No
Reviewed on Oct 25, 2026
The Ashbrook Hotel
Price was $721, price is now $701 per person
$701
per person
Dec 25 - Dec 27
found 10 hours ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Book a stay at this business-friendly hotel in Frankfort. Enjoy free WiFi, free parking, and meeting facilities. Popular attractions Buffalo Trace Distillery and Liberty Hall are located nearby.
Wonderful experience, we only spent 1 night but next time will stay longer. Great staff and wonderful bar!
Reviewed on Oct 28, 2026
Prestonsburg Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Prestonsburg Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Nov 7 - Tue, Nov 17
DAB
Daytona Beach Intl.
LEX
Blue Grass
$522 Roundtrip, found 2 days ago
$522
Roundtrip
found 2 days ago
Tue, Nov 3 - Tue, Nov 17
DAB
Daytona Beach Intl.
LEX
Blue Grass
$523 Roundtrip, found 2 days ago
$523
Roundtrip
found 2 days ago
Sat, Nov 7 - Sat, Nov 14
DAB
Daytona Beach Intl.
LEX
Blue Grass
$536 Roundtrip, found 2 days ago
$536
Roundtrip
found 2 days ago
Fri, Nov 6 - Tue, Nov 17
DAB
Daytona Beach Intl.
LEX
Blue Grass
$610 Roundtrip, found 2 days ago
$610
Roundtrip
found 2 days ago
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