Winchester Vacations from $603

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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.
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
Price was $637, price is now $603 per person
$603
per person
May 9 - May 11
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
8.6/10 Excellent! (1,097 reviews)
Breakfast was great. Remodeling going on in lobby and atrium but room was fine.

Reviewed on Mar 29, 2026

Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $815, price is now $777 per person
$777
per person
May 1 - May 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.2/10 Very Good! (1,063 reviews)
Wasn't expecting the train noise. Very convenient to downtown. Staff was very nice

Reviewed on Mar 20, 2026

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was $1,533, price is now $1,476 per person
$1,476
per person
May 19 - May 23
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Lexington (LEX)
8.8/10 Excellent! (1,007 reviews)
Beautiful property! Rooms were great.

Reviewed on Mar 29, 2026

Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

3 out of 5
Price was $1,419, price is now $1,384 per person
$1,384
per person
May 19 - May 23
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Lexington (LEX)
8.4/10 Very Good! (611 reviews)
Hotel looks great in the photos but it’s kind of

Reviewed on Mar 26, 2026

MainStay Suites Georgetown Lexington North

MainStay Suites Georgetown Lexington North

2.5 out of 5
Price was $770, price is now $705 per person
$705
per person
May 21 - May 25
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Lexington (LEX)
7.4/10 Good! (218 reviews)
Room was clean, the light switch in the bathroom needed to be fixed. I couldnt figure out how to turn the shower on but that was a me problem i guess. Overall it was a decent stay.

Reviewed on Mar 30, 2026

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Discover the most popular places to visit in Winchester

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
Kentucky Horse Park

Kentucky Horse Park

4.5/5(332 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
Horse barn in Kentucky

Keeneland Racing Course

4.5/5(267 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

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

$99
per adult
Distillery District Food & History Tour in Lexington
Woodford Reserve, Kismet Thoroughbred Farm & Whiskey Thief

Woodford Reserve, Kismet Thoroughbred Farm & Whiskey Thief

$275
per adult
100% of travellers recommend
Woodford Reserve, Kismet Thoroughbred Farm & Whiskey Thief
See all activities in Winchester

Winchester Hotel Deals

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
Fully refundable
$88 nightly
The price is $102 total per night from Apr 5 to Apr 6
$102 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (2,180 reviews)
Clean easy to check in.

Reviewed on Mar 29, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $257 total per night from Apr 5 to Apr 6
$257 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (1,208 reviews)
Awesome bar. Great drinks. Staff was super friendly across the board. Shout out to Sam, the valet, who offered to shuttle us to our dinner resrvations. Stand up guy. Walls are a little thin. Heard some things I wish I didn't, BUT 5 stars. Highly recommend.

Reviewed on Mar 28, 2026

The Manchester
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $123 total per night from Apr 26 to Apr 27
$123 total
Apr 26 - Apr 27
Total with taxes and fees
9.4/10 Exceptional! (1,061 reviews)
This hotel was fine and clean, but the room had a special thermostat to keep the temperature of the room between 68 and 72. However, it wasn't very regulated and we were either freezing because the heat wouldn't come on or burning up because it wouldn't turn off. The pillows were uncomfortable, but ...

Reviewed on Mar 29, 2026

Elwood Hotel & Suites
See all 1,187 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 $603 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.