Winchester Vacations from $375

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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.
Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

2.5 out of 5
Price was $486, price is now $375 per person
$375
per person
Jan 28 - Feb 1
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
8/10 Very Good! (1,004 reviews)
No room in bathroom had a few spots that had to be cleaned. No the girl at the desk was far from friendly.

Reviewed on Dec 18, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $697, price is now $538 per person
$538
per person
Jan 28 - Feb 1
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Great hotel and location.

Reviewed on Dec 15, 2025

Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
Price was $585, price is now $478 per person
$478
per person
Jan 28 - Feb 1
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
9.6/10 Exceptional! (462 reviews)
Clean room, and the social time was a nice touch.

Reviewed on Dec 18, 2025

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
Price was $597, price is now $491 per person
$491
per person
Jan 28 - Feb 1
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
8.6/10 Excellent! (1,034 reviews)
The first floor is currently under renovation and is noisy and dusty. It would be better if the area could be covered.

Reviewed on Dec 28, 2025

Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
South Broadway Park
Price was $539, price is now $447 per person
$447
per person
Jan 28 - Feb 1
found 1 hour ago
Roundtrip non-stop flight included
San Diego (SAN) to Lexington (LEX)
9.2/10 Wonderful! (774 reviews)
Everything was amazing, everyone was super nice, the room was very clean and comfy close to the hospital because we had to be there at 5:30am… it was also my birthday so… I was so happy with my stay!

Reviewed on Dec 22, 2025

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Discover the most popular places to visit in Winchester

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
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
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

Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

$105
per adult
Bites of the Bluegrass Cocktails & Bites Tour
Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon Tour

Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon Tour

$275
per adult
Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon 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

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Jan 1 to Jan 2
$98 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.

Reviewed on Dec 14, 2025

Best Western Winchester Hotel
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

2.5 out of 5
100 Winchester Plaza Winchester KY
Fully refundable
$88 nightly
The price is $97 total per night from Jan 4 to Jan 5
$97 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (526 reviews)
Very friendly staff. Room was clean and spacious.

Reviewed on Dec 22, 2025

Holiday Inn Express Lexington East - Winchester by IHG
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $215 total per night from Dec 29 to Dec 30
$215 total
Dec 29 - Dec 30
Total with taxes and fees
9.4/10 Exceptional! (1,093 reviews)
Lovely hotel, comforting woodsy scent infused, nice big walk-in shpwer

Reviewed on Dec 22, 2025

The Manchester
See all 1,185 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 $375 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.

Explore a world of travel with Expedia

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