Deals on vacations and trips to Winchester

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Top Winchester hotel deals

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 $67 per night
$67
per night
Apr 29 - Apr 30
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.
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

3.5 out of 5
245 Lexington Green Circle, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $144 per night
$144
per night
May 6 - May 7
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the seasonal outdoor pool and free perks like cooked-to-order breakfast and free self parking.
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
1935 Stanton Way, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $106 per night
$106
per night
May 1 - May 2
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.
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 $66 per night
$66
per night
May 5 - May 6
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.
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike, Lexington, KY
Free Cancellation
Reserve now, pay when you stay
The price is $117 per night
$117
per night
May 12 - May 13
This smoke-free 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
The price is $169 per night
$169
per night
May 6 - May 7
This smoke-free hotel features 2 restaurants and 2 bars/lounges. WiFi in public areas is free. Valet parking, express check-in, and express check-out are also offered.
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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

Image for Kentucky Horse Park

Kentucky Horse Park

4.5/5(328 reviews)

Explore the lovely green spaces of Kentucky Horse Park and enjoy the horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
Image for University of 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
Image for Fayette Mall

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?
With Travelocity vacation packages, you could live it up in Winchester from just . Hotels, adventures and flights — we’ve got you. You’ll save loads just for bundling together your bookings. And with all that taken care of before you even set off, you don’t have to worry about a thing.
How long should my Winchester vacation be?
There are no rules for how long your Winchester vacation should be, but the majority of travelers stay around 2 nights. Got some leeway with your departure date? Extend your vacation by a couple of extra nights. Then you’ll have ample time to explore the area’s off-the-beaten-path gems as well.
Where can I get the best vacation package deals for Winchester?
Check out Travelocity. With access to 400 airline partners and an impressive 1,000,000 properties worldwide, finding the best Winchester package deal couldn’t be simpler.
Why should I purchase my Winchester vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the beginning. Enjoy a fulfilling travel experience knowing you can rely on our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you can rest easy knowing you’re getting the best deal available.
Will I save money on my Winchester car rental if I combine it with a hotel or flight?
Absolutely — combine your car, hotel and flight into a Winchester vacation package and you’ll save tons. With so much to discover in the Winchester area, that rental vehicle will make exploring a breeze. Once you’re in the driver’s seat, turn up the tunes and head to Churchill Downs, a famous attraction about 90 mi from Winchester.
What is the best time of year to go to Winchester?
May, August and October are the most popular months to visit, while December, January and February are generally quieter. If you’ve got a limited budget, you’d be better off visiting in . is usually regarded as the costliest month to come here.
Which airport is best for Winchester?
Blue Grass Airport (LEX) is about 25 mi west of central Winchester.
What is there to do in Winchester?
There is an undeniable magic as you wander through the streets of Winchester. Bluegrass Heritage Museum and Southwind Golf Course are just a couple of renowned sights that lure visitors to this fantastic city, so put them at the top of your to-do list.
Where should I stay when visiting Winchester?
The Best Western Winchester Hotel is popular with many travelers. Book as soon as possible before it’s too late.