Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $823, price is now $744 per person
$744
per person
May 22 - May 25
found 4 hours ago
Roundtrip flight included
New York (NYC) 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

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $1,107, price is now $905 per person
$905
per person
Apr 24 - Apr 26
found 23 hours ago
Roundtrip flight included
New York (NYC) 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.
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
Price was $1,066, price is now $944 per person
$944
per person
Apr 24 - Apr 26
found 23 hours ago
Roundtrip flight included
New York (NYC) 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.
The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $967, price is now $866 per person
$866
per person
May 22 - May 25
found 4 hours ago
Roundtrip flight included
New York (NYC) 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.
Courtyard Lexington Keeneland/Airport

Courtyard Lexington Keeneland/Airport

3 out of 5
Beaumont Residential
Price was $980, price is now $888 per person
$888
per person
May 22 - May 25
found 4 hours ago
Roundtrip flight included
New York (NYC) 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

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 22 - Mar 23
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
$217 nightly
The price is $252 total per night
$252 total
Mar 29 - Mar 30
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 29 - Mar 30
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
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
$133 nightly
The price is $155 total per night
$155 total
Mar 29 - Mar 30
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
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
$106 nightly
The price is $123 total per night
$123 total
Mar 29 - Mar 30
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
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $75 total per night
$75 total
Mar 29 - Mar 30
Total with taxes and fees
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. Guests will appreciate freebies like continental 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

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
Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(329 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
Horse barn in Kentucky

Keeneland Racing Course

4.5/5(262 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 $744. 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
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 🚣