Deals on vacations and trips to Winchester

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Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was $1,052, price is now $851 per person
$851
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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 and free WiFi in public areas. Enjoy the free continental breakfast each morning.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was $1,281, price is now $1,011 per person
$1,011
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Lexington (LEX)
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.
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was $1,200, price is now $962 per person
$962
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,178, price is now $987 per person
$987
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Lexington (LEX)
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.
The Delegate

The Delegate

3.5 out of 5
Price was $1,686, price is now $1,427 per person
$1,427
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.

Top Winchester hotels deals

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Free Cancellation
$88 nightly
The price is $102 total per night
$102 total
Mar 15 - Mar 16
Total with taxes and fees
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
The Manchester

The Manchester

4 out of 5
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.
Pet friendly
Free WiFi
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $113 total per night
$113 total
Mar 22 - Mar 23
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.
Pet friendly
Parking included
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
1375 South Broadway Lexington KY
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $104 total per night
$104 total
Mar 22 - Mar 23
Total with taxes and fees
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.
Pet friendly
Free WiFi
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $147 total per night
$147 total
Mar 15 - Mar 16
Total with taxes and fees
This luxury 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
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
2100 Hackney Pl Lexington KY
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $93 total per night
$93 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. 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
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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 showing land animals

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.

Kentucky Horse Park
Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky

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.

University of Kentucky
Horse barn in Kentucky

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.

Keeneland Racing Course

Frequently asked questions

How much are vacation packages to Winchester?
Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $851. Providing both flights and hotels, these great deals make it simple to explore all corners of the world.
How long should my Winchester vacation be?
There's no hard and fast rule for how long you should spend in Winchester, but many people opt to stay around 2 nights. Got some leeway with your departure date? Consider extending your trip by a couple of extra nights. That way, you'll have ample time to check out the nearby areas too.
Where can I get the best vacation package deals for Winchester?
You'll discover a tempting selection of Winchester package deals on Travelocity. With as many as 400 partner airlines and 1,000,000 properties around the globe, organizing your ideal getaway will be easy.
Why should I book my Winchester vacation package via Travelocity?
Nothing tops the peace of mind knowing you've scored the best price in town — that's our Price Match Guarantee. Add to that our impressive range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a hassle-free vacation.
Can I save money on my Winchester car rental if I bundle it with hotels and flights?
Absolutely — bundle your car, hotel and flight into a Winchester vacation package and you'll save a handsome sum. With so much to see in Winchester, having your own set of wheels will make it easy to explore. Once you're in the driver's seat, turn up the stereo and head toward Churchill Downs, a top attraction around 90 mi from Winchester.
Which airport is best for Winchester?
Blue Grass Airport (LEX), the main terminal in Winchester, is where you'll come in to land. It's situated 25 mi west of the downtown area.
What is there to do in Winchester?
Winchester has more than its fair share of sights to discover, such as Bluegrass Heritage Museum and Lykins Park. These two impressive attractions top most tourists' to-do lists.
Where should I stay when visiting Winchester?
If you're after somewhere to base yourself, take a look at the Best Western Winchester Hotel. It's the top choice for many visitors.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings
Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Canoeing down the Kentucky river 🚣