Winchester Vacations from $334

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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
Price was $395, price is now $334 per person
$334
per person
May 14 - May 17
found 10 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Lexington (LEX)
8.2/10 Very Good! (599 reviews)
Clean room and friendly staff. Quite nice.

Reviewed on Feb 26, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Save 100% on your flight
Price was $792, price is now $592 per person
$592
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Provided non down pillows. Got us in early. Very accommodating.

Reviewed on Feb 23, 2026

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $1,229, price is now $1,031 per person
$1,031
per person
May 8 - May 11
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (838 reviews)
I have stayed there several times. Always enjoyable. Clean and friendly.

Reviewed on Feb 4, 2026

Home2 Suites Lexington Keeneland Airport, KY

Home2 Suites Lexington Keeneland Airport, KY

3 out of 5
Beaumont Residential
Price was $713, price is now $618 per person
$618
per person
May 8 - May 11
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.8/10 Exceptional! (234 reviews)
Clean rooms and friendly staff

Reviewed on Feb 15, 2026

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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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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
Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, 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
Horse barn in Kentucky

Keeneland Racing Course

4.5/5(259 reviews)

Enjoy a trip to Keeneland Racing Course and popular activities like horseback riding in Lexington. You can attend a sporting event while in the area.

Keeneland Racing Course

What to do in Winchester

Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

$105
per adult
Bites of the Bluegrass Cocktails & Bites Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

$99
per adult
Distillery District Food & History Tour in Lexington
See all activities in Winchester

Winchester Hotel Deals

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $234 total per night from Mar 22 to Mar 23
$234 total
Mar 22 - Mar 23
Total with taxes and fees
9.6/10 Exceptional! (1,174 reviews)
Very nice clean room and staff was very friendly and accommodating

Reviewed on Feb 26, 2026

The Manchester
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $134 total per night from Mar 12 to Mar 13
$134 total
Mar 12 - Mar 13
Total with taxes and fees
8.8/10 Excellent! (1,013 reviews)
Everything was nice.

Reviewed on Feb 23, 2026

DoubleTree Suites by Hilton Hotel 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
$155 nightly
The price is $180 total per night from Mar 12 to Mar 13
$180 total
Mar 12 - Mar 13
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Yes everything was good!

Reviewed on Feb 20, 2026

Hilton Lexington/Downtown
See all 1,169 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 $334 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.

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