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.

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

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$165 per night from 16 Feb to 17 Feb
AU$165
includes taxes & fees
16 Feb - 17 Feb
9.2/10 Wonderful! (2,276 reviews)
"Very nice with a decent breakfast."

Reviewed on 6 Feb. 2025

GLō Best Western Lexington
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$258 per night from 21 Feb to 22 Feb
AU$258
includes taxes & fees
21 Feb - 22 Feb
8.2/10 Very Good! (1,004 reviews)
"Nothing. All good."

Reviewed on 7 Feb. 2025

Hilton Lexington/Downtown
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 23 Feb to 24 Feb
AU$187
includes taxes & fees
23 Feb - 24 Feb
8.4/10 Very Good! (1,001 reviews)
"Had to pay for parking"

Reviewed on 7 Feb. 2025

Embassy Suites by Hilton Lexington/UK Coldstream
See all 1,098 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?
You’ll find cheap prices on Expedia for your Winchester escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
December, January and February are the best times to search for cheap Winchester holiday packages. Travelling in quieter months means you can generally find better prices on accommodation and flights.
How many days is enough for Winchester?
With a well-organised travel plan, you can easily visit the most popular Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester holiday for longer.
Is it worth booking a holiday package to Winchester?
Known for its dining, nature and plenty of other highlights, you can be certain Winchester is a good holiday destination. Some of the most popular attractions to add to your itinerary? Don’t miss Bluegrass Heritage Museum and Lykins Park during your Winchester holiday.
How to find the best Winchester package deals?
Use Expedia’s handy filters to help you find some of the best Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Winchester package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to lock in your holiday package well in advance.
Is it cheaper to book a Winchester holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You’ll usually snag a better deal than booking each component individually. And you’ll still enjoy the freedom to create a personalised Winchester holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Winchester?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Winchester adventure.
How to plan a trip to Winchester?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Winchester.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Winchester.
  3. Decide how long to go away for: Now that you know more about Winchester, you can work out the right length of your holiday. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your accommodation and airfare: After you’ve nailed down your travel dates and duration, lock in the ideal Winchester holiday package for you.

Discover the most popular places to visit in Winchester

Kentucky Horse Park

Kentucky Horse Park

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

Kentucky Horse Park
The Kentucky Castle

The Kentucky Castle

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

The Kentucky Castle

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

Experience Rebecca Ruth Chocolate Tour & Museum: Group limit 15

Experience Rebecca Ruth Chocolate Tour & Museum!

AU$16
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

AU$48
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Experience Rebecca Ruth Chocolate Tour & Museum: Group limit 15

Experience Rebecca Ruth Chocolate Tour & Museum

AU$16
per adult
Experience Rebecca Ruth Chocolate Tour & Museum
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.