Deals on vacations and trips to Winchester

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The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was $732, price is now $607 per person
$607
per person
Aug 11 - Aug 14
found 3 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) 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.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $846, price is now $666 per person
$666
per person
Aug 11 - Aug 14
found 3 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) 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 $800, price is now $654 per person
$654
per person
Aug 11 - Aug 14
found 3 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) 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.
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
Price was $741, price is now $614 per person
$614
per person
Aug 11 - Aug 14
found 3 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Lexington (LEX)
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.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $779, price is now $647 per person
$647
per person
Aug 11 - Aug 14
found 3 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Free self parking and a coffee shop are also offered on site.

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
$76 nightly
The price is $83 total per night
$83 total
Jul 26 - Jul 27
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
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $72 total per night
$72 total
Jul 1 - Jul 2
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
$120 nightly
The price is $140 total per night
$140 total
Jul 1 - Jul 2
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.
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
Jul 26 - Jul 27
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
$111 nightly
The price is $129 total per night
$129 total
Jul 26 - Jul 27
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
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
$141 nightly
The price is $155 total per night
$155 total
Jul 12 - Jul 13
Total with taxes and fees
This cabin features a restaurant, a seasonal outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area is provided and the front desk is staffed around-the-clock.
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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

Two horses in a grassy field with trees in the background.

Kentucky Horse Park

4.5/5(333 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
A large campus with a central building, a circular lawn, and surrounding trees with autumn foliage.

University of Kentucky

4.5/5(389 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
A mechanical assembly line with bottles and brass figurines.

Buffalo Trace Distillery

4.5/5(219 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 $607. 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

An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.
A historic downtown area with a prominent clock tower and a green-roofed building.
A town with a prominent red brick church, a clock tower, and a large parking lot.
A brick building with a central entrance, columns, and the name 'Winchester Hall' above the door.
A clear river with visible rocks and a rocky cliff in the background.