Winchester Vacation Packages

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Your Winchester Vacation

Take away the hard part of organizing your next epic adventure with a Winchester vacation package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.

Winchester Hotel Deals

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 CA $139 per night from Jun. 6 to Jun. 7
CA $139
CA $161 total
includes taxes & fees
Jun 6 - Jun 7
9.2/10 Wonderful! (2,265 reviews)
"Very nice refurbished"

Reviewed on May 27, 2024

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 CA $174 per night from Jun. 20 to Jun. 21
CA $174
CA $202 total
includes taxes & fees
Jun 20 - Jun 21
9.2/10 Wonderful! (1,003 reviews)
Great Stay!
"Lexington is a beautiful city to visit and this hotel made the stay even better! We had been on our trip for two weeks when we got to the Embassy Suites. This is a beautiful hotel with an excellent staff, complimentary cocktails during happy hour and a great breakfast. This was our best stay over ..."

Reviewed on May 21, 2024

Embassy Suites by Hilton Lexington Green
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Jun. 9 to Jun. 10
CA $92
CA $106 total
includes taxes & fees
Jun 9 - Jun 10
8/10 Very Good! (1,000 reviews)
It was ok
"This place was fine for one night, traveling through the area. But I probably will not stay again. We booked a room for 2 adults and 1 child. We got a room with one queen bed. I assumed that meant there would be a cot or something for the child. But when we asked, they said they didn’t have cots. ..."

Reviewed on May 26, 2024

GuestHouse Lexington
See all 1,200 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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(7 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(15 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 The Kentucky Castle

The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

What to do in Winchester

Image for Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

Lexington: Ashland Henry Clay Estate Ticket with Guided Tour

CA $34
Per adult
80% of travellers recommend
Lexington: Ashland Henry Clay Estate Ticket with Guided Tour
Image for Bourbon Boat Tour in Frankfort with Tasting

Bourbon Boat Tour in Frankfort with Tasting

CA $122
Per adult
Bourbon Boat Tour in Frankfort with Tasting
Image for Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

CA $134
Per adult
Distillery District Food & History Tour in Lexington
See all activities in Winchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.