Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Sleep Inn

Sleep Inn

2.5 out of 5
Price was $229, price is now $186 per person
$186
per person
Feb 27 - Mar 2
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Comfort Suites Georgetown

Comfort Suites Georgetown

2.5 out of 5
Price was $252, price is now $201 per person
$201
per person
Feb 27 - Mar 2
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
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. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $880, price is now $706 per person
$706
per person
Mar 5 - Mar 8
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $399, price is now $323 per person
$323
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip non-stop 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.
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was $781, price is now $690 per person
$690
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.

Top Winchester hotels deals

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
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 19 - Jan 20
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

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr Winchester KY
$106 nightly
The price is $117 total per night
$117 total
Feb 15 - Feb 16
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

Baymont by Wyndham Winchester

2.5 out of 5
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 18 - Jan 19
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

The Manchester

4 out of 5
941 Manchester St Lexington KY
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $213 total per night
$213 total
Jan 25 - Jan 26
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

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
209 RUCCIO WAY Lexington KY
Free Cancellation
$97 nightly
The price is $113 total per night
$113 total
Jan 19 - Jan 20
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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
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 18 - Jan 19
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
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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

A panoramic picture of the gorgeous University of Kentucky Campus.

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 is a working horse farm and an educational theme park opened in 1978 in Lexington, Kentucky. It is located off Kentucky State Highway 1973 (Iron Works Pike) and Interstate 75, at Exit 120, in northern Fayette County in the United States. The equestrian facility is a 1,224-acre

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
The bottling line for the special single barrel Blantons Bourbon.

Buffalo Trace Distillery

4.5/5(218 reviews)

You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.

Buffalo Trace Distillery

Frequently asked questions

How much are vacation packages to Winchester?
Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $186. 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

Photo by Hyelsinta
Photo by Hyelsinta