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

The Sire Hotel Lexington, Tapestry Collection by Hilton
per person
Aug 19 - Aug 22
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
Stay at this 3.5-star 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 The Red Mile Racetrack are located nearby.

La Quinta Inn Lexington/Horse Park
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 3-star 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 Rupp Arena and Kentucky Horse Park are located nearby.

Tru by Hilton University Medical Center
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Red Mile Racetrack and Kroger Field are located nearby.

Origin Lexington a Wyndham Hotel
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 3.5-star 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 The Red Mile Racetrack are located nearby.

Home2 Suites by Hilton Georgetown
per person
Jul 14 - Jul 17
just found
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 3-star business-friendly hotel in Georgetown. 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 The Pavillion are located nearby.

Home2 Suites By Hilton Richmond, Ky
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 3-star hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Richmond Centre Mall and Cinemark At Richmond Centre are located nearby.

The Campbell House Lexington, Curio Collection by Hilton
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 4-star business-friendly hotel in Lexington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions The Red Mile Racetrack and Kroger Field are located nearby.

Bluegrass Extended Stay Hotel
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this business-friendly motel in Lexington. 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 Kroger Field and Rupp Arena are located nearby.
Winchester Vacation Packages 3-4 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.

Tue, Jul 1 - Thu, Jul 10
IAH
George Bush Intercontinental
LEX
Blue Grass
$228 Roundtrip, just found
$228
Roundtrip
just found

Fri, Jul 4 - Wed, Jul 9
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$249 Roundtrip, just found
$249
Roundtrip
just found

Fri, Sep 5 - Sat, Sep 6
SAN
San Diego Intl.
LEX
Blue Grass
$253 Roundtrip, just found
$253
Roundtrip
just found

Tue, Aug 26 - Wed, Sep 3
DFW
Dallas-Fort Worth Intl.
LEX
Blue Grass
$258 Roundtrip, found 2 days ago
$258
Roundtrip
found 2 days ago
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