Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Conference Center Lexington North
Price was $511, price is now $442 per person
$442
per person
Feb 27 - Mar 2
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this family-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.
21c Museum Hotel Lexington
Price was $622, price is now $500 per person
$500
per person
Feb 27 - Mar 2
found 10 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 Red Mile Racetrack and Kroger Field are located nearby.
Embassy Suites by Hilton Lexington/UK Coldstream
Price was $698, price is now $570 per person
$570
per person
Feb 27 - Mar 2
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Red Mile Racetrack and Kentucky Horse Park are located nearby.
The Sire Hotel Lexington, Tapestry Collection by Hilton
Price was $725, price is now $610 per person
$610
per person
Feb 27 - Mar 2
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this 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 Red Mile Racetrack and Kroger Field are located nearby.
Capital Plaza Hotel
Price was $613, price is now $534 per person
$534
per person
Apr 11 - Apr 14
found 23 hours ago
Roundtrip flight included
Boston (BOS) 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.
The Campbell House Lexington, Curio Collection by Hilton
Price was $573, price is now $501 per person
$501
per person
Feb 27 - Mar 2
found 10 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.
Comfort Suites Keeneland
Price was $704, price is now $625 per person
$625
per person
Feb 22 - Mar 1
found 1 day 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 Kroger Field and Red Mile Racetrack are located nearby.
Home2 Suites by Hilton Lexington University / Medical Center
Price was $499, price is now $445 per person
$445
per person
Feb 27 - Mar 2
found 10 hours 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 WiFi, and a 24-hour fitness center. 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.
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.
Tue, Apr 21 - Tue, Apr 28
SAN
San Diego Intl.
LEX
Blue Grass
$217 Roundtrip, found 9 hours ago
$217
Roundtrip
found 9 hours ago
Tue, Apr 21 - Tue, Apr 28
CLD
McClellan-Palomar
LEX
Blue Grass
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Tue, Apr 7 - Wed, Apr 15
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$269 Roundtrip, found 9 hours ago
$269
Roundtrip
found 9 hours ago
Fri, Jan 30 - Tue, Feb 3
IAH
George Bush Intercontinental
LEX
Blue Grass
$286 Roundtrip, found 5 days ago
$286
Roundtrip
found 5 days ago
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