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An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Winchester Vacations from $470

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The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Free daily buffet breakfast
    Aug 27 - Aug 30

    Clarion Hotel Conference Center Lexington North + Flight

    Lexington
    3 nights
    3.0 star property
    7.6/10 - Good (1,007 reviews)
    "nope"
    Reviewed July 21, 2026
    Roundtrip • Los Angeles (LAX) - Lexington (LEX)
    LAX - LEX • 1 stop LEX - LAX • 1 stop
    $532
    $470
    per traveler
    found 1 day ago
    Clarion Hotel Conference Center Lexington North
  • Exterior
    Aug 27 - Aug 30

    Montgomery Inn BnB + Flight

    Versailles
    3 nights
    4.0 star property
    9.4/10 - Exceptional (113 reviews)
    "The lady who owned the property was nice. She let us know where everything was and her dog was super sweet and walked with us to our room. The property itself was much older and not maintained well, but if she was the groundskeeper too I’d say it would be hard to manage. We couldn’t find a way to Lock the door from the outside, which was an issue if we left to go somewhere. Town wasn’t far from the property but not really walkable. The room wasn’t dirty per-say, but hadn’t been swept well and..."
    Reviewed July 19, 2026
    Roundtrip • Los Angeles (LAX) - Lexington (LEX)
    LAX - LEX • 1 stop LEX - LAX • 1 stop
    $717
    $582
    per traveler
    found 1 day ago
    Montgomery Inn BnB
  • Lobby sitting area
    Aug 27 - Aug 30

    Capital Plaza Hotel + Flight

    Frankfort
    3 nights
    3.0 star property
    8.0/10 - Very Good (1,057 reviews)
    "When we arrived we learned that the property was under renovation. We were not aware of this at the time I booked, maybe I overlooked it but even so. No hot water, no AC in the lobby. Squatters on park benches in the parking garage area"
    Reviewed July 19, 2026
    Roundtrip • Los Angeles (LAX) - Lexington (LEX)
    LAX - LEX • 1 stop LEX - LAX • 1 stop
    $630
    $537
    per traveler
    found 1 day ago
    Capital Plaza Hotel
  • Bar (on property)
    Oct 16 - Oct 18

    The Sire Hotel Lexington, Tapestry Collection by Hilton + Flight

    Downtown Lexington
    2 nights
    3.5 star property
    9.4/10 - Exceptional (892 reviews)
    "This hotel was a nice place to stay for one evening. Comfortable room and easy parking. Breakfast was fine - would have appreciated a little more variety. But what really makes this hotel stand out is the staff. Every person - from the guest specialist who first greeted us to the woman in the breakfast area- was so exceptionally kind and friendly. Definitely added to my list of good places to stay in Lexington!"
    Reviewed July 21, 2026
    Roundtrip • New York (NYC) - Lexington (LEX)
    EWR - LEX • 1 stop LEX - LGA • Nonstop
    $929
    $813
    per traveler
    found 1 day ago
    The Sire Hotel Lexington, Tapestry Collection by Hilton
  • BBQ/picnic area
    Aug 27 - Aug 30

    Residence Inn Lexington Keeneland/Airport + Flight

    Beaumont Residential
    3 nights
    3.0 star property
    9.0/10 - Wonderful (621 reviews)
    Roundtrip • Los Angeles (LAX) - Lexington (LEX)
    LAX - LEX • 1 stop LEX - LAX • 1 stop
    $577
    $509
    per traveler
    found 1 day ago
    Residence Inn Lexington Keeneland/Airport

Discover the most popular places to visit in Winchester

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.

Winchester Hotel Deals

In-room safe, desk, laptop workspace, blackout drapes

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
2.2 mi from Winchester
9.4 out of 10, Exceptional, (583 reviews)
"had a very pleasant stay. The room was clean, the staff was consistently friendly and helpful, and the breakfast was excellent. Everything ran smoothly, and I appreciated the overall comfort and service throughout my visit."
$81 nightly
The price is $90
Aug 9 - Aug 10
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG
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.
See all properties in Winchester

Frequently Asked Questions

How much does a Winchester vacation package cost?

You'll find cheap prices from $470 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.