Winchester Vacations from $506

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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 Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $594, price is now $506 per person
$506
per person
Jun 25 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Lexington (LEX)
8.2/10 Very Good! (1,054 reviews)
Simple checkin and parking. Hospitable staff. Undergoing renovation in main areas, which I knew when booked. It should be nice when they are done. Spacious but outdated room. Carpet was very old and stained and smelled like dog when we did not bring a pet ourselves so shouldn’t have been put in that room. Pet rooms should be allocated to guests with pets. Breakfast subpar. Walkable to historical downtown which was really cool. Also had free trolley tour hop on and off which stopped right inside parking structure. Very convenient. Did chocolate candy tour and was fun.

Reviewed on Apr 19, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $752, price is now $591 per person
$591
per person
Jun 25 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Lexington (LEX)
8.8/10 Excellent! (1,001 reviews)
This hotel was great! The location is right in the center of the downtown area. They also use phenomenal products in their showers. The body wash, shampoo and conditioner was some of the best I have ever used in a hotel. The valet service was great as well as the front desk staff! 10/10 would recommend to anyone heading to Lexington.

Reviewed on Apr 15, 2026

The Manchester

The Manchester

4 out of 5
Distillery District
Price was $767, price is now $622 per person
$622
per person
Jun 25 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Lexington (LEX)
9.6/10 Exceptional! (1,211 reviews)
Staff was professional and courteous. Room was perfect, mini bar had everything you could think of. Would highly recommend this property.

Reviewed on Apr 20, 2026

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $699, price is now $590 per person
$590
per person
Jun 25 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Lexington (LEX)
9.4/10 Exceptional! (104 reviews)
With terrible weather, travel issues regarding further travel (1/31/26 )storm , frigid temps, Pam provided a warm and inviting place to stay

Reviewed on Feb 2, 2026

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
Price was $657, price is now $569 per person
$569
per person
Jun 25 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Lexington (LEX)
9.4/10 Exceptional! (2,180 reviews)
Staff were helpful and nice. Clean room

Reviewed on Apr 20, 2026

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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
$80 nightly
The price is $88 total per night from Apr 30 to May 1
$88 total
Apr 30 - May 1
Total with taxes and fees
7.2/10 Good! (787 reviews)
It was a great experience

Reviewed on Apr 16, 2026

Baymont by Wyndham Winchester
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $83 total per night from May 19 to May 20
$83 total
May 19 - May 20
Total with taxes and fees
8.8/10 Excellent! (436 reviews)
Room was clean, pool was nice and cool, staff was great

Reviewed on Apr 16, 2026

Spark by Hilton Lexington Hamburg
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
$98 nightly
The price is $114 total per night from May 3 to May 4
$114 total
May 3 - May 4
Total with taxes and fees
9.4/10 Exceptional! (2,184 reviews)
Staff were helpful and nice. Clean room

Reviewed on Apr 20, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
See all 1,192 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 $506 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.