Deals on vacations and trips to Winchester
Save when you book Winchester package deals
Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Sleep Inn
Price was $604, price is now $538 per person
$538
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Lexington (LEX)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Embassy Suites by Hilton Lexington/UK Coldstream
Price was $867, price is now $763 per person
$763
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Lexington (LEX)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free full breakfast each morning.
Home2 Suites by Hilton Lexington Hamburg
Price was $788, price is now $709 per person
$709
per person
Apr 9 - Apr 12
found 24 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Lexington (LEX)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
The Delegate
Price was $766, price is now $690 per person
$690
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Lexington (LEX)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and express check-out are also offered on site.
21c Museum Hotel Lexington
Downtown Lexington
Price was $748, price is now $676 per person
$676
per person
Apr 26 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.
Top Winchester hotels deals
The Manchester
941 Manchester St Lexington KY
Free Cancellation
Reserve now, pay when you stay
$203 nightly
The price is $236 total per night
$236 total
Mar 22 - Mar 23
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, express check-in, and express check-out are also offered.
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $137 total per night
$137 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. Self parking, a business center, and a coffee shop are also offered.
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $175 total per night
$175 total
Mar 31 - Apr 1
Total with taxes and fees
This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the express check-out, laundry service, and free airport shuttle. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Hyatt Regency Lexington
401 W High St Lexington KY
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $166 total per night
$166 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Elwood Hotel & Suites
444 Parkway Drive Lexington KY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $108 total per night
$108 total
Mar 11 - Mar 12
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby fireplace, express check-out, and dry cleaning are also on offer.
Holiday Inn Lexington - Hamburg by IHG
1976 Justice Dr Lexington KY
Free Cancellation
$96 nightly
The price is $111 total per night
$111 total
Mar 13 - Mar 14
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Kentucky Horse Park
4.5/5(328 reviews)
Enjoy a trip to Kentucky Horse Park and popular activities like horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
4.5/5(384 reviews)
Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Keeneland Racing Course
4.5/5(259 reviews)
Enjoy a trip to Keeneland Racing Course and popular activities like horseback riding in Lexington. You can attend a sporting event while in the area.
Frequently asked questions
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