Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Tru by Hilton University Medical Center
Price was $510, price is now $452 per person
$452
per person
Jul 31 - Aug 2
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 Red Mile Racetrack and Keeneland Racing Course are located nearby.
Montgomery Inn BnB
Price was $1,131, price is now $871 per person
$871
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
Stay at this B&B in Versailles. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Nostalgia Station Toy Train Museum and Raintree Gallery and Framing are located nearby.
21c Museum Hotel Lexington
Price was $762, price is now $606 per person
$606
per person
Jul 31 - Aug 2
found 1 day 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 Hamburg Place are located nearby.
The Sire Hotel Lexington, Tapestry Collection by Hilton
Price was $802, price is now $653 per person
$653
per person
Jul 31 - Aug 2
found 1 day 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 Hamburg Place are located nearby.
Capital Plaza Hotel
Price was $927, price is now $762 per person
$762
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.
DoubleTree Suites by Hilton Hotel Lexington
Price was $545, price is now $466 per person
$466
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
Stay at this hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Hamburg Place and Red Mile Racetrack are located nearby.
Courtyard Lexington South/Hamburg Place
Price was $569, price is now $498 per person
$498
per person
Jul 31 - Aug 2
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 Hamburg Place and Red Mile Racetrack are located nearby.
Residence Inn Lexington Keeneland/Airport
Price was $552, price is now $488 per person
$488
per person
Jul 31 - Aug 2
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 WiFi, and a free airport shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Red Mile Racetrack and Keeneland Racing Course are located nearby.
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.
Sat, Sep 19 - Tue, Oct 6
JFK
John F. Kennedy Intl.
LEX
Blue Grass
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Fri, Jul 17 - Sat, Jul 18
IAH
George Bush Intercontinental
LEX
Blue Grass
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Wed, Jul 22 - Tue, Jul 28
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$316 Roundtrip, found 18 hours ago
$316
Roundtrip
found 18 hours ago
Fri, Jun 12 - Mon, Jun 15
HOU
William P. Hobby
LEX
Blue Grass
$321 Roundtrip, found 3 days ago
$321
Roundtrip
found 3 days ago
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