Deals on vacations and trips to Winchester
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Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington
Price was $436, price is now $403 per person
$403
per person
Feb 20 - Feb 22
found 10 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.
21c Museum Hotel Lexington
Downtown Lexington
Price was $538, price is now $465 per person
$465
per person
Feb 20 - Feb 22
found 10 hours ago
Roundtrip non-stop flight included
Charleston (CHS) 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.
The Campbell House Lexington, Curio Collection by Hilton
Price was $518, price is now $465 per person
$465
per person
Feb 20 - Feb 22
found 10 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a picnic area are also offered.
Embassy Suites by Hilton Lexington/UK Coldstream
Price was $511, price is now $460 per person
$460
per person
Feb 20 - Feb 22
found 9 hours ago
Roundtrip non-stop flight included
Charleston (CHS) 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.
Holiday Inn Lexington - Hamburg by IHG
Price was $447, price is now $412 per person
$412
per person
Feb 20 - Feb 22
found 9 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
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.
Top Winchester hotels deals
Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
Free Cancellation
Reserve now, pay when you stay
The price is $80 total per night
$80 total
per night
Jan 18 - Jan 19
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A seasonal outdoor pool and a computer station are also provided.
Pool
Breakfast included
Hampton Inn Winchester
1025 Early Dr Winchester KY
The price is $136 total per night
$136 total
per night
Jan 25 - Jan 26
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Free Cancellation
Reserve now, pay when you stay
The price is $88 total per night
$88 total
per night
Jan 18 - Jan 19
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
The Manchester
941 Manchester St Lexington KY
Free Cancellation
Reserve now, pay when you stay
The price is $225 total per night
$225 total
per night
Feb 1 - Feb 2
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.
Pet friendly
Free WiFi
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
100 Canebrake Drive Lexington KY
Free Cancellation
Reserve now, pay when you stay
The price is $105 total per night
$105 total
per night
Jan 14 - Jan 15
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Staybridge Suites Lexington S Medical Ctr Area by IHG
209 RUCCIO WAY Lexington KY
Free Cancellation
The price is $113 total per night
$113 total
per night
Jan 22 - Jan 23
This hotel features an indoor pool and a gym. Business travelers can take advantage of the 24-hour business center. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
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.
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.
Fayette Mall
4.5/5(321 reviews)
You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.
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