Winchester Vacations from $461

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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.
Capital O 3Y Motel Mount Vernon Renfro Valley

Capital O 3Y Motel Mount Vernon Renfro Valley

2.5 out of 5
Price was $563, price is now $461 per person
$461
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
5.4/10 (49 reviews)
The staff was nice and the room was clean just needs some major renovations!

Reviewed on Apr 20, 2026

Rose Hill Inn

Rose Hill Inn

4 out of 5
Price was $710, price is now $630 per person
$630
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
10/10 Exceptional! (71 reviews)
Absolutely fabulous stay! Very spacious and comfortable room. The hosts were great - they called twice on Christmas, the day we were arriving, to ensure we had the codes to enter and details for our stay. Breakfast was great and they were accommodating to our allergies. Beautiful bed and breakfast. Will definitely be back!

Reviewed on Dec 30, 2025

Sweet Victory Bed and Breakfast

Sweet Victory Bed and Breakfast

3.5 out of 5
Price was $677, price is now $601 per person
$601
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
10/10 Exceptional! (26 reviews)
The hosts were very friendly. The breakfast was hot and fresh. The whole property was very nuce and well maintained.

Reviewed on May 19, 2026

Home2 Suites by Hilton Danville

Home2 Suites by Hilton Danville

3 out of 5
Price was $654, price is now $581 per person
$581
per person
Jul 16 - Jul 19
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Lexington (LEX)
No reviews
Clarion Pointe Harrodsburg-Danville

Clarion Pointe Harrodsburg-Danville

2.5 out of 5
Price was $560, price is now $509 per person
$509
per person
Jul 16 - Jul 19
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Lexington (LEX)
7.2/10 Good! (585 reviews)
Hotel was close to the event we were supposed to to attend but got rained out. How ever, price seemed high compared to what was offered with the hotel. Bathroom was extremely small. Secured door did not lock from coming from the outside of the hotel. Breakfast was ok.

Reviewed on May 29, 2026

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Discover the most popular places to visit in Winchester

Kentucky Horse Park

Kentucky Horse Park

4.5/5(333 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(389 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
Buffalo Trace Distillery

Buffalo Trace Distillery

4.5/5(219 reviews)

You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.

Buffalo Trace Distillery

What to do in Winchester

Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon Tour

Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour

$275
per adult
Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

$125
per adult
Distillery District Food & History Tour in Lexington
Lexington's Art Walk Tour

Lexington's Art Walk Tour

$40
per adult
Lexington's Art Walk 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
$82 nightly
The price is $91 total per night from Jun 10 to Jun 11
$91 total
Jun 10 - Jun 11
Total with taxes and fees
7.2/10 Good! (804 reviews)
"Great beds and friendly staff"

Reviewed on May 31, 2026

Baymont by Wyndham Winchester
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
$96 nightly
The price is $112 total per night from Jun 22 to Jun 23
$112 total
Jun 22 - Jun 23
Total with taxes and fees
9.4/10 Exceptional! (2,207 reviews)
"Breakfast staff was very helpful"

Reviewed on May 30, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Jun 28 to Jun 29
$103 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (1,157 reviews)
"For a La Quinta, this place is top tier. Clean facility, easy parking, nice location, staff was very friendly and helpful, room was nice, air worked great, bds were comfy - no complaints. Only observation was that the bathroom had a "fishy" water smell, which I think was from the shower drain but ..."

Reviewed on May 29, 2026

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
See all 1,191 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 $461 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.