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.
Capital Plaza Hotel
Price was $997, price is now $873 per person
$873
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
This hotel features a restaurant, an indoor pool, and a bar/lounge. There's a gym on site, and laundry facilities and concierge services are also offered.
21c Museum Hotel Lexington
Downtown Lexington
Price was $1,204, price is now $987 per person
$987
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Sire Hotel Lexington, Tapestry Collection by Hilton
Downtown Lexington
Price was $1,272, price is now $1,109 per person
$1,109
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a terrace are also offered.
Residence Inn Lexington Keeneland/Airport
Beaumont Residential
Price was $1,212, price is now $1,068 per person
$1,068
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and free buffet breakfast each morning.
Courtyard Lexington Keeneland/Airport
Beaumont Residential
Price was $1,178, price is now $1,042 per person
$1,042
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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, 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.
Top Winchester hotels deals
Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $80 total per night
$80 total
Jan 18 - Jan 19
Total with taxes and fees
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
$126 nightly
The price is $139 total per night
$139 total
Feb 8 - Feb 9
Total with taxes and fees
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
$76 nightly
The price is $83 total per night
$83 total
Jan 14 - Jan 15
Total with taxes and fees
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
$184 nightly
The price is $214 total per night
$214 total
Jan 26 - Jan 27
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.
Pet friendly
Free WiFi
Staybridge Suites Lexington S Medical Ctr Area by IHG
209 RUCCIO WAY Lexington KY
Free Cancellation
$97 nightly
The price is $113 total per night
$113 total
Jan 22 - Jan 23
Total with taxes and fees
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
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
100 Canebrake Drive Lexington KY
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $105 total per night
$105 total
Jan 15 - Jan 16
Total with taxes and fees
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
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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