Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Comfort Suites

Comfort Suites

2.5 out of 5
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Home2 Suites by Hilton Georgetown

Home2 Suites by Hilton Georgetown

3 out of 5
per person
Aug 14 - Aug 18
found 16 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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 free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

2 out of 5
per person
Aug 14 - Aug 18
found 16 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Lexington (LEX)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. The front desk is staffed around-the-clock and concierge services are on offer.

Top Winchester hotels deals

The Manchester

The Manchester

4 out of 5
941 Manchester St, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $225 total per night
$225 total
per night
Jun 29 - Jun 30
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
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $77 total per night
$77 total
per night
Jun 15 - Jun 16
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
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $126 total per night
$126 total
per night
Jun 29 - Jun 30
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.
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
The price is $78 total per night
$78 total
per night
Jul 2 - Jul 3
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
The price is $127 total per night
$127 total
per night
Jun 15 - Jun 16
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
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
1801 Newtown Pike, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $117 total per night
$117 total
per night
Jun 29 - Jun 30
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.
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)

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
The Kentucky Castle

The Kentucky Castle

4.5/5(24 reviews)

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.

The Kentucky Castle

Frequently asked questions

How much are vacation packages to Winchester?
Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $397. 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