![](https://forever.travel-assets.com/flex/flexmanager/images/2020/11/06/TVLY-MSJE-DTG-Hero-Image.jpg?impolicy=fcrop&w=900&h=225&q=mediumHigh)
Deals on vacations and trips to Winchester
Save when you book Winchester package deals
Top Winchester hotels deals
![GLō Best Western Lexington](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/5f9daec3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
GLō Best Western Lexington
1935 Stanton Way, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $93 per night
$93
per night
Jul 2 - Jul 3
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a snack bar/deli, and express check-out are also on offer.
Pool
Breakfast included
![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/0b8cf614_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
GuestHouse Lexington
2261 Elkhorn Road, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $71 per night
$71
per night
Jun 23 - Jun 24
This hotel doesn't skimp on freebies - guests receive free buffet 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.
Pool
Breakfast included
![Marriott Lexington Griffin Gate Golf Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/79f835ef_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $86 per night
$86
per night
Jul 2 - Jul 3
This smoke-free resort features a golf course, a full-service spa, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the indoor pool and perks like free self parking.
Pool
Hot Tub
![Quality Inn Lexington -Horse Park](https://images.trvl-media.com/lodging/1000000/30000/22700/22656/0acfaafe_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Quality Inn Lexington -Horse Park
1938 Stanton Way, Bldg A, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $71 per night
$71
per night
Jun 24 - Jun 25
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
![Embassy Suites by Hilton Lexington Green](https://images.trvl-media.com/lodging/1000000/10000/1600/1598/3f8a45a7_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Embassy Suites by Hilton Lexington Green
245 Lexington Green Circle, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $127 per night
$127
per night
Jul 2 - Jul 3
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the seasonal outdoor pool and free perks like cooked-to-order breakfast and free self parking.
Pool
Breakfast included
![The Manchester](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/57d46aa8_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Manchester
941 Manchester St, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $144 per night
$144
per night
Jul 2 - Jul 3
This smoke-free hotel features 2 restaurants and 2 bars/lounges. WiFi in public areas is free. Valet parking, express check-in, and express check-out are also offered.
Pet friendly
Free WiFi
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
Explore the lovely green spaces of Kentucky Horse Park and enjoy the horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
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.
The Kentucky Castle
Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Photos of local treasures
Browse Winchester vacation photos for more inspiration
Frequently asked questions
Top all inclusive vacation packages with airfare
Book a vacation to Winchester
Most popular
Hotels
Hotels with an Indoor Pool in GeorgetownHotels with an Indoor Pool in RichmondHotels in VersaillesHotels in MidwayHotels in ClarksvilleHotels with Hot Tubs in GeorgetownPet Friendly Hotels in GeorgetownHotels in GeorgetownHotels in ShepherdsvilleHotels with Hot Tubs in RichmondHotels in NicholasvilleHotels in FrankfortHotels in ShelbyvilleHotels in RichmondHotels in JeffersonvilleHotels in New Albany
Cars