Winchester Holidays

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Your Winchester Holiday

Our Winchester holiday packages give you the power to create your own adventure. Tailor your journey to your interests and style and make the most of your time in this wonderful city. You'll want to go sightseeing during your trip to Winchester. Drop by big-name attractions such as Lykins Park, Southwind Golf Course and Bluegrass Heritage Museum. Browse Expedia's wide range of travel options and book your ideal holiday to Winchester now.

Beautiful view of the beach with palm trees

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Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Blue Grass Airport (LEX)
Population
18,400
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course

Our pick of the best 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 AU$103 per night from 24 Dec to 25 Dec
AU$103
includes taxes & fees
24 Dec - 25 Dec
8.2/10 Very Good! (1,328 reviews)
"Stuff was so nice."

Reviewed on 21 Nov. 2024

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 AU$149 per night from 26 Nov to 27 Nov
AU$149
includes taxes & fees
26 Nov - 27 Nov
9.2/10 Wonderful! (2,229 reviews)
"I felt like my bed sheets were not clean"

Reviewed on 19 Nov. 2024

GLō Best Western Lexington
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$120 per night from 26 Nov to 27 Nov
AU$120
includes taxes & fees
26 Nov - 27 Nov
8/10 Very Good! (1,075 reviews)
"Room was very spacious and clean and it was comfortable to stay in. Breakfast was good and had several options."

Reviewed on 19 Nov. 2024

GuestHouse Lexington
See all 1,113 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Winchester holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Winchester from just . And the more you bundle, the more cash you save. Your dream holiday 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 holiday 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 Centre in this neighbourhood, 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 travellers.
How far in advance should I book my Winchester holiday?
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 travelling 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 holiday 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 holiday package?
You sure can, and we’ll help you every step of the way. You may be able to change or cancel your Winchester holiday 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

Shriners Hospitals for Children

If Shriners Hospitals for Children is what brings you to town, hopefully you'll have a chance to explore more of Lexington.

Shriners Hospitals for Children

What to do in Winchester

Lexington: Thoroughbred Horse Farm Tour and Keeneland Visit

Lexington: Thoroughbred Horse Farm Tour and Keeneland Visit

AU$64
Per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Keeneland Visit
Experience Rebecca Ruth Chocolate Tour & Museum: Group limit 15

Experience Rebecca Ruth Chocolate Tour & Museum!

AU$15
Per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Full Day Bourbon Experience

Full Day Bourbon Experience

AU$380
Per adult
Full Day Bourbon Experience
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.