Winchester Vacations from $520

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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.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn

Sleep Inn

2.5 out of 5
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Lexington (LEX)
8.2/10 Very Good! (536 reviews)
The hotel was clean, the breakfast was great.

Reviewed on Jul 9, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Oct 9 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Wonderful hotel that used to be an old bank. Amazing room and amenities. Would definitely stay again.

Reviewed on Jul 13, 2025

Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
per person
Oct 9 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Lexington (LEX)
8.8/10 Excellent! (974 reviews)
Rooms were super spacious and every one of the staff members I came in contact with her top notch!

Reviewed on Jun 30, 2025

MainStay Suites Georgetown Lexington North

MainStay Suites Georgetown Lexington North

2.5 out of 5
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Lexington (LEX)
7.4/10 Good! (202 reviews)
The pool was cloudy and I did not feel safe putting my kids in it. Breakfast was cold and did not last the full time it was to be open. We came down at 8am and most of the food was gone with no refills.

Reviewed on Jun 26, 2025

Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
Downtown Lexington
per person
Oct 9 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Lexington (LEX)
8.6/10 Excellent! (1,008 reviews)
This property is old and in serious need of updating. The Expedia pictures do not match the property itself. This property was way overpriced for its condition. There was so much dust behind the mirror in the bathroom I actually saw a dust bunny fall.

Reviewed on Jul 11, 2025

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Discover the most popular places to visit in Winchester

Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(328 reviews)

Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country.

Kentucky Horse Park
In a hores eye #2

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
It's beginning to look a lot like Christmas.

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

What to do in Winchester

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

$30
per traveler
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

$10
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

$99
per adult
Lexington: Downtown Walking Food & History Tour
See all activities in Winchester

Winchester Hotel Deals

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $88 total per night from Jul 27 to Jul 28
$88 total
Jul 27 - Jul 28
Total includes taxes and fees
7/10 Good! (719 reviews)
"Quick stay after delayed flight. It had what we needed. Free breakfast that we were not expecting"

Reviewed on Jul 4, 2025

Baymont by Wyndham Winchester
Spark by Hilton Lexington Hamburg
Spark by Hilton Lexington Hamburg
2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Jul 25 to Jul 26
$78 total
Jul 25 - Jul 26
Total includes taxes and fees
8.8/10 Excellent! (54 reviews)
"Good"

Reviewed on Jul 12, 2025

Spark by Hilton Lexington Hamburg
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $179 total per night from Aug 8 to Aug 9
$179 total
Aug 8 - Aug 9
Total includes taxes and fees
8.4/10 Very Good! (1,009 reviews)
"Properrty is downtown. After sunset it us not a great neighborhood."

Reviewed on Jul 12, 2025

Hilton Lexington/Downtown
See all 1,143 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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Blue Grass Airport (LEX)
Population
18,400
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $520 on Expedia for your Winchester escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation 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 vacation packages. Opting to travel in less busy periods means you can typically find better prices on flights and accommodations.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to hit all the top sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Winchester?
Whether you're planning to discover attractions like Bluegrass Heritage Museum and Lykins Park, or eager to experience its terrific dining and nature, a Winchester vacation guarantees an unforgettable adventure. Book your trip with Expedia and find out why Winchester is such a good vacation destination.
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 vacation package well in advance.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation 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 personalized Winchester vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Secure your perfect escape to Winchester with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck --- we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.