Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington
Price was $563, price is now $508 per person
$508
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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 Rupp Arena and Kroger Field are located nearby.
21c Museum Hotel Lexington
Price was $1,896, price is now $1,516 per person
$1,516
per person
Apr 9 - Apr 13
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Hyatt Place Lexington
Price was $825, price is now $681 per person
$681
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Rupp Arena are located nearby.
Capital Plaza Hotel
Price was $613, price is now $532 per person
$532
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Elwood Hotel & Suites
Price was $851, price is now $742 per person
$742
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Home2 Suites by Hilton Lexington Hamburg
Price was $869, price is now $767 per person
$767
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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 Kroger Field and Rupp Arena are located nearby.
Courtyard Lexington South/Hamburg Place
Price was $1,196, price is now $1,074 per person
$1,074
per person
Apr 23 - Apr 26
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 WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Kroger Field and Rupp Arena are located nearby.
The Campbell House Lexington, Curio Collection by Hilton
Price was $1,495, price is now $1,352 per person
$1,352
per person
Apr 9 - Apr 13
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Kroger Field 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, Apr 21 - Tue, Apr 28
SAN
San Diego Intl.
LEX
Blue Grass
$244 Roundtrip, found 8 hours ago
$244
Roundtrip
found 8 hours ago
Sat, Jun 13 - Tue, Jun 16
DEN
Denver Intl.
LEX
Blue Grass
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Tue, Apr 21 - Tue, Apr 28
CLD
McClellan-Palomar
LEX
Blue Grass
$255 Roundtrip, found 2 hours ago
$255
Roundtrip
found 2 hours ago
Tue, Jun 23 - Wed, Jul 8
IAH
George Bush Intercontinental
LEX
Blue Grass
$289 Roundtrip, found 1 hour ago
$289
Roundtrip
found 1 hour ago
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