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Hillsboro Vacation Packages

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Hillsboro Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Georgetown - Lexington North

Red Roof Inn Georgetown - Lexington North

2 out of 5
Price was $478, price is now $461 per person
$461
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Price was $673, price is now $621 per person
$621
per person
Dec 25 - Dec 27
found 2 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

Montgomery Inn BnB

4 out of 5
Price was $746, price is now $702 per person
$702
per person
Dec 25 - Dec 27
found 2 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.

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond

2 out of 5
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.

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

2 out of 5
Price was $503, price is now $475 per person
$475
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Book a stay at this business-friendly hotel in Georgetown. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Horse Park and The Pavillion are located nearby.
Great for an overnight stay.

Reviewed on Oct 26, 2026

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $707, price is now $674 per person
$674
per person
Dec 25 - Dec 27
found 2 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

Elwood Hotel & Suites

4 out of 5
Price was $650, price is now $626 per person
$626
per person
Dec 25 - Dec 27
found 2 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

The Aldenberg Hotel

2 out of 5
Price was $742, price is now $718 per person
$718
per person
Dec 25 - Dec 27
found 2 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

Hillsboro Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

2 out of 5
Price was $503, price is now $475 per person
$475
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $663, price is now $589 per person
$589
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $645, price is now $594 per person
$594
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $663, price is now $616 per person
$616
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Lexington (LEX)

Hillsboro Vacation Packages 5-7 Night Stays

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

GuestHouse Lexington

2.5 out of 5
Price was $583, price is now $544 per person
$544
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $722, price is now $646 per person
$646
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
South Broadway Park
Price was $679, price is now $625 per person
$625
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $952, price is now $885 per person
$885
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Nov 19 - Thu, Dec 3
ATL
Hartsfield-Jackson Atlanta Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to Cincinnati - Northern Kentucky Intl., returning Thu, Dec 3, priced at $59 just found
Frontier Airlines
Wed, Dec 2 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$118 Roundtrip, found 2 hours ago
$118
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Dallas-Fort Worth Intl. to Cincinnati - Northern Kentucky Intl., returning Wed, Dec 16, priced at $118 found 2 hours ago
Frontier Airlines
Wed, Dec 2 - Sat, Dec 5
DEN
Denver Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Dec 2 from Denver Intl. to Cincinnati - Northern Kentucky Intl., returning Sat, Dec 5, priced at $138 just found
Frontier Airlines
Wed, Dec 2 - Wed, Dec 9
LAX
Los Angeles Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Los Angeles Intl. to Cincinnati - Northern Kentucky Intl., returning Wed, Dec 9, priced at $167 found 4 hours ago