Search Deals onPrestonsburg Vacation Packages
Prestonsburg Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Microtel Inn by Wyndham Lexington
Price was $489, price is now $443 per person
$443
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Hamburg Place and Red Mile Racetrack are located nearby.
No indoor pool that was whole reason I changed booking from outside pool to inside pool I put it in ementities along with breakfast and pet . After we checked in my grandkids got in there swim gear only to come back with papaw telling me no pool I was so disappointed for them that’s what our trip was for .
Reviewed on Jun 20, 2026

Origin Lexington a Wyndham Hotel
Price was $746, price is now $664 per person
$664
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Red Mile Racetrack and Cinemark Fayette Mall are located nearby.
The hotel is a beautiful, quaint, quiet yet trendy property. Nice bar/restaurant inside adjacent to lobby. Tons of great shopping and dining within walking distance. Ample onsite parking.
Reviewed on Jun 30, 2026

La Quinta Inn Lexington/Horse Park
Price was $547, price is now $487 per person
$487
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Kentucky Horse Park and Red Mile Racetrack are located nearby.
Nice clean hotel.
Reviewed on Jun 29, 2026

Homewood Suites by Hilton Lexington Fayette Mall
Price was $676, price is now $606 per person
$606
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Keeneland Racing Course are located nearby.
Great stay.
Reviewed on Jun 29, 2026

GuestHouse Lexington
Price was $553, price is now $497 per person
$497
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 breakfast and the helpful staff in our reviews. Popular attractions Hamburg Place and Red Mile Racetrack are located nearby.
Amazing bed, spacious room, very clean
Reviewed on Jun 30, 2026

Holiday Inn Lexington - Hamburg by IHG
Price was $627, price is now $566 per person
$566
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Hamburg Place and Red Mile Racetrack are located nearby.
The hotel is convenient and close to the interstate and Hamburg. Our room was clean enough and the bed was comfortable. Our one complaint was the overpowering scent of disinfectant in the room with a slight musty odor, maybe from the carpet? My eyes were burning...we almost asked for another room.we have stayed at this hotel in the past with no issues. Maybe the age is showing on the property.
Reviewed on Jun 28, 2026

The Campbell House Lexington, Curio Collection by Hilton
Price was $722, price is now $653 per person
$653
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Red Mile Racetrack and Keeneland Racing Course are located nearby.
Hotel is in a perfect location and we really enjoyed our stay! The rooms are a little old but kind of expected. I noticed the staff never tended to the fruit infused water station but that’s the only complaint. Coffee and staff was fantastic!
Reviewed on Jun 29, 2026

DoubleTree Suites by Hilton Hotel Lexington
Price was $655, price is now $596 per person
$596
per person
Sep 17 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Lexington (LEX)
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 Red Mile Racetrack and Lexington Ice Center are located nearby.
The hotel was a nice hotel and unique with its design of interior rooms with balconies. It had a charming Kentucky feel. The issue was the cleaning of the room. We checked in on Thursday and had to extend our stay, upon check in, until Sunday. After the first night, our room was not cleaned and when asked, I was told by the young man at the front desk that we had to request the room to be cleaned. We travel a lot and I have never heard of this. Also, it was not told to us upon check in, nor when we made the reservation. I cleaned the room myself that night. When we went to dinner, I stopped by the front desk and was told by the other person at the front desk that we didn’t have to make a request to have the room cleaned. So we were getting different information from staff working for the same company. They did clean our room while we were out on Saturday; however, they didn’t go a good job. They left the dirty drinking glasses on the table; didn’t provide clean glasses; didn’t vacuum; didn’t straighten the couch; didn’t provide new bottle water, etc., etc. etc. Unfortunately, this left an unfavorable impression. I will say that Margot, at the front desk, was awesome! Very pleasant and tried to be as helpful as possible.
Reviewed on Jun 29, 2026
Prestonsburg Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



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