Deals on vacations and trips to Winchester

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Baymont by Wyndham Corbin

Baymont by Wyndham Corbin

2.5 out of 5
per person
Sep 13 - Sep 20
found 16 hours ago
Roundtrip flight included
Dallas (DFW) 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.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Aug 23 - Aug 25
just found
Roundtrip non-stop flight included
Miami (MIA) 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 Manchester

The Manchester

4 out of 5
Distillery District
per person
Aug 23 - Aug 25
just found
Roundtrip non-stop flight included
Miami (MIA) to Lexington (LEX)
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.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
per person
Aug 23 - Aug 25
just found
Roundtrip non-stop flight included
Miami (MIA) 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 Delegate

The Delegate

3.5 out of 5
per person
Sep 26 - Sep 28
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Free self parking is offered and the front desk is staffed around-the-clock.

Top Winchester hotels deals

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
$80 nightly
The price is $88 total per night
$88 total
Jul 20 - Jul 21
Total includes 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
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
$67 nightly
The price is $78 total per night
$78 total
Jul 25 - Jul 26
Total includes 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
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $165 total per night
$165 total
Jul 20 - Jul 21
Total includes taxes and fees
This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the express check-out, laundry service, and free airport shuttle. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Pool
Free airport shuttle
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $82 total per night
$82 total
Jul 20 - Jul 21
Total includes taxes and fees
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
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $127 total per night
$127 total
Jul 21 - Jul 22
Total includes 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
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
Jul 29 - Jul 30
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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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)

Explore Kentucky Horse Park, a favorite green space in Lexington, and also enjoy the area's horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
In a hores eye #2

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
It's beginning to look a lot like Christmas.

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.

Fayette Mall

Frequently asked questions

How much are vacation packages to Winchester?
Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $338. 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

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Photo by Hyelsinta
Photo by Hyelsinta