Deals on vacations and trips to Winchester

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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
$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
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
$118 nightly
The price is $137 total per night
$137 total
Mar 15 - Mar 16
Total with taxes and fees
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
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
$151 nightly
The price is $175 total per night
$175 total
Mar 31 - Apr 1
Total with 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
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $166 total per night
$166 total
Apr 5 - Apr 6
Total with taxes and fees
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.
Pool
Free airport shuttle
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $108 total per night
$108 total
Mar 12 - Mar 13
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
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

3 out of 5
1976 Justice Dr Lexington KY
Free Cancellation
$96 nightly
The price is $111 total per night
$111 total
Mar 13 - Mar 14
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Parking 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 . 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 🚣