Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was $494, price is now $475 per person
$475
per person
Dec 4 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
This hotel doesn't skimp on freebies - guests receive free continental 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.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $623, price is now $543 per person
$543
per person
Dec 4 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $616, price is now $579 per person
$579
per person
Dec 4 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $571, price is now $541 per person
$541
per person
Dec 4 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
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.
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

2.5 out of 5
Price was $534, price is now $516 per person
$516
per person
Dec 4 - Dec 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Lexington (LEX)
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a grocery/convenience store, and express check-out are also offered.

Top Winchester hotels deals

Comfort Inn Winchester

Comfort Inn Winchester

2.5 out of 5
5250 Revilo Rd Winchester KY
Free Cancellation
$76 nightly
The price is $84 total per night
$84 total
Nov 28 - Nov 29
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's dry cleaning and multilingual staff can provide around-the-clock assistance.
Parking included
Free WiFi
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Free Cancellation
Reserve now, pay when you stay
$53 nightly
The price is $59 total per night
$59 total
Nov 11 - Nov 12
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.
Pet friendly
Parking included
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way Lexington KY
Free Cancellation
$60 nightly
The price is $69 total per night
$69 total
Nov 30 - Dec 1
Total with 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
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Free Cancellation
$71 nightly
The price is $83 total per night
$83 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental 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
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
167 West Main Street Lexington KY
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $172 total per night
$172 total
Dec 1 - Dec 2
Total with taxes and fees
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.
Pet friendly
Free WiFi
Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Free Cancellation
$79 nightly
The price is $92 total per night
$92 total
Dec 1 - Dec 2
Total with taxes and fees
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-in are also on offer.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Stay near popular Winchester attractions

Winchester Traveling Trail

Explore the great outdoors at Winchester Traveling Trail, a lovely green space in Winchester. You can enjoy the restaurants while in the area.
See properties

Frequently asked questions

How much are vacation packages to Winchester?
Adventure calls in Winchester, with Travelocity vacation packages starting from as low as $475. 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.