Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Prestonsburg next to Mountain Arts Center
Price was $580, price is now $514 per person
$514
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Book a stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mountain Arts Center and Archer Park are located nearby.
GuestHouse Lexington
Price was $1,013, price is now $864 per person
$864
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 Kroger Field and Red Mile Racetrack are located nearby.
Comfort Inn Pikeville
Price was $689, price is now $595 per person
$595
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Stay at this inn in Pikeville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pikeville Mini-Park and Memorial Park are located nearby.
Comfort Suites Prestonsburg West
Price was $645, price is now $562 per person
$562
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
Book a stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Mountain Arts Center and Archer Park are located nearby.
Hotel LEX, Trademark Collection by Wyndham
Price was $1,106, price is now $965 per person
$965
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Capital Plaza Hotel
Price was $950, price is now $834 per person
$834
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Lexington (LEX)
Stay at this hotel in Frankfort. Enjoy room service, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Buffalo Trace Distillery and Old State Capitol are located nearby.
Comfort Suites Georgetown
Price was $934, price is now $826 per person
$826
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Lexington (LEX)
Book a stay at this business-friendly hotel in Georgetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kentucky Horse Park and The Pavillion are located nearby.
Comfort Inn Lexington South
Price was $954, price is now $846 per person
$846
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Lexington (LEX)
Book a stay at this business-friendly hotel in Nicholasville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Camp Nelson National Monument and Jessamine Creek Gorge Preserve are located nearby.
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winchester 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.
Thu, May 28 - Sat, May 30
DEN
Denver Intl.
LEX
Blue Grass
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago
Tue, Jun 23 - Wed, Jul 8
IAH
George Bush Intercontinental
LEX
Blue Grass
$277 Roundtrip, found 5 hours ago
$277
Roundtrip
found 5 hours ago
Sat, Sep 19 - Tue, Oct 6
JFK
John F. Kennedy Intl.
LEX
Blue Grass
$281 Roundtrip, just found
$281
Roundtrip
just found
Thu, Jun 4 - Thu, Jun 11
HOU
William P. Hobby
LEX
Blue Grass
$296 Roundtrip, found 2 days ago
$296
Roundtrip
found 2 days ago
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