Search Deals onPrestonsburg Vacation Packages
Prestonsburg Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
HomeTowne Studios by Red Roof Georgetown - Lexington North
Price was $642, price is now $611 per person
$611
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this hotel in Georgetown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Kentucky Horse Park and Cherry Blossom Golf and Country Club are located nearby.
Hotel Lex and Conference Center, Trademark Collection
Price was $703, price is now $660 per person
$660
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lexington Sporting Club Youth Complex and Boone Station State Historic Site are located nearby.
Montgomery Inn BnB
Price was $779, price is now $732 per person
$732
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.
We love visiting this BnB! We have stayed twice now and love the charm and privacy. Breakfast is amazing and the owner is super helpful! Super cute town and close to lots of distilleries and other activities.
Reviewed on Nov 12, 2026
Holiday Inn Lexington - Hamburg by IHG
Price was $732, price is now $696 per person
$696
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Super 8 by Wyndham Richmond
Price was $634, price is now $612 per person
$612
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Clean room, well lit parking, friendly staff.
Reviewed on Nov 10, 2026
Red Roof Inn Georgetown - Lexington North
Price was $635, price is now $613 per person
$613
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Stay at this hotel in Georgetown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Horse Park and Cherry Blossom Golf and Country Club are located nearby.
The room was very basic but clean and comfortable and met my needs for the night. The location was close to the many tourist stops on my trip. Would definitely choose this property on some future trip to this area.
Reviewed on Nov 2, 2026
SpringHill Suites by Marriott Lexington Near the University of Kentucky
Price was $783, price is now $760 per person
$760
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Red Mile Racetrack and Rupp Arena are located nearby.
Great stay. Clean room and staff was very nice
Reviewed on Nov 10, 2026
Holiday Inn Express Lexington - Horse Park Area by IHG
Price was $723, price is now $708 per person
$708
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
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 Kentucky Horse Park and Rupp Arena are located nearby.
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.
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