Winchester Vacations

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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
Fully refundableReserve now, pay when you stay
The price is NT$2,177 per night from May 28 to May 29
NT$2,177
per night
May 28 - May 29
8.4/10 Very Good! (956 reviews)
"Very nice and great price."

Reviewed on 2024/5/12

Quality Inn Lexington -Horse Park
GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NT$3,430 per night from May 20 to May 21
NT$3,430
per night
May 20 - May 21
9.2/10 Wonderful! (2,256 reviews)
Clean and comfortable
"Very clean and prompt professional help."

Reviewed on 2024/5/11

GLō Best Western Lexington
Embassy Suites by Hilton Lexington Green
Embassy Suites by Hilton Lexington Green
3.5 out of 5
245 Lexington Green Circle, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NT$4,326 per night from May 28 to May 29
NT$4,326
per night
May 28 - May 29
9.2/10 Wonderful! (1,006 reviews)
"We liked the atmosphere and the breakfast"

Reviewed on 2024/5/12

Embassy Suites by Hilton Lexington Green
See all 1,224 properties in Winchester
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.

Frequently asked questions

How much does a Winchester vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Winchester from just . And the more you bundle, the more cash you save. Your dream vacation has never been so affordable.
How do I get a cheap travel package to Winchester?
Browse and lock in everything in one place with our Winchester vacation packages. You’ll discover bargains on hotels, flights, tours and more that’ll keep your hip pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 properties globally to pick from, you’ll have endless opportunities to mix and match however you please.
Where should I stay in Winchester?
With popular attractions such as Bluegrass Heritage Museum and Clark Regional Medical Center in this neighborhood, try to find a hotel near either of them. Community Park is another sight in Winchester that draws in the crowds.
What are the top hotels in Winchester?
If this will be your first visit to Winchester, secure a room at Holiday Inn Express Lexington East - Winchester, an IHG Hotel or 2nd Story Historic Downtown 2bedroom With Modern Amenities. Both hotels offer friendly service and are popular options with lots of travelers.
How far in advance should I book my Winchester vacation?
While prices change frequently, we generally recommend booking your seats as early as possible. Most international fares become available on Expedia up to a year in advance. If you’re booking last minute, you might still be lucky. Cheap journeys to Winchester sometimes emerge only weeks before departure.
What does an Expedia Winchester travel package include?
Hotels, rental cars and flights, or any combination of the three — it’s up to you! Whether you’re visiting Winchester with the whole family or traveling with your friends, there’s a package to fit your budget and style. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking a Winchester travel package?
A travel package can be tailored to your budget and is a simple way to stretch your hard-earned dollars. How much you include is up to you. Hotels, rental cars and flights — come up with a combination that suits your style.
Can I choose my airline with a Winchester Expedia vacation package?
You certainly can. We offer more than 550 partner airlines throughout the world, so opt for the carrier that best suits your budget needs.
If I'm not able to travel, can I cancel my Winchester vacation package?
You sure can, and we’ll help you every step of the way. You may be able to change or cancel your Winchester vacation package at no cost within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If life throws you a curveball, browse our Customer Service Portal for further information.

Discover the most popular places to visit in Winchester

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 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 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

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.