Winchester Vacations from $821

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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 $941, price is now $821 per person
$821
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $1,383, price is now $1,103 per person
$1,103
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
8.8/10 Excellent! (1,005 reviews)
Very friendly staff. I felt so welcomed and cared for. Bedroom was very comfortable and great sizes. The bathroom has marble walls and floor and very spacious. It was a nice experience.

Reviewed on Mar 6, 2026

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 out of 5
Price was $1,335, price is now $1,137 per person
$1,137
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
8.6/10 Excellent! (1,097 reviews)
Everything was great, the service, cleanliness of the room, and the food; the only thing I could complain about is the unknown parking fee that was added for each day of stay. There was no mentioning of parking fee when I checked-in and there was not any "special parking designated for paying guest to park.

Reviewed on Mar 17, 2026

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $1,262, price is now $1,087 per person
$1,087
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (1,010 reviews)
Clean room and friendly staff, third time staying here and will definitely recommend

Reviewed on Mar 10, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,158, price is now $1,012 per person
$1,012
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (1,046 reviews)
Everything at the hotel was excellent. Room, staff, restaurant, and bar. Plenty of restaurants and things to do. It was just a couple blocks from University of Kentucky campus.

Reviewed on Mar 24, 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 showing land animals

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

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, 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
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
$80 nightly
The price is $93 total per night from Mar 29 to Mar 30
$93 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (2,170 reviews)
I would like you to call it by the name that’s on the property holiday inn express as arriving at 1am we drove up and down looking for best western! Otherwise great stay.

Reviewed on Mar 25, 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! (1,206 reviews)
Hotel and room was beautiful. Upscale without being snooty. Very clean. Check in staff were just okay. No water or anything offered. No ice on any floor and had to go down to bar for a glass of ice. Mini fridge is so packed w hotel beverages for purchase there is no room for your own. No iron/board ...

Reviewed on Mar 23, 2026

The Manchester
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $170 total per night from Mar 29 to Mar 30
$170 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (629 reviews)
Stayed for 3 nights. Room was great, restaurant on site was great and walkable to other places

Reviewed on Mar 24, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
See all 1,177 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 $821 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.