Winchester Vacations from $883

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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.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $1,044, price is now $883 per person
$883
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Lexington (LEX)
9.4/10 Exceptional! (1,008 reviews)
The room was clean. The staff were helpful!

Reviewed on Jul 6, 2026

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $1,152, price is now $960 per person
$960
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Lexington (LEX)
9.4/10 Exceptional! (110 reviews)
Yes

Reviewed on Jun 14, 2026

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was $1,096, price is now $920 per person
$920
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
This hotel was very nice, very clean and the staff was amazing! Great place to stay

Reviewed on Jul 5, 2026

Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm

3 out of 5
Price was $1,077, price is now $914 per person
$914
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Lexington (LEX)
9.2/10 Wonderful! (373 reviews)
Good stay.

Reviewed on Jun 28, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $1,155, price is now $984 per person
$984
per person
Sep 14 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
It’s in a historical landmark building so I get that it’s old. But the tile floors were pretty dingy looking. The corners in the rooms seemed to be overlooked when cleaned. Very convenient location to bars and restaurants. Staff was great.

Reviewed on Jun 25, 2026

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Stay near popular Winchester attractions

Bluegrass Heritage Museum

7.4/10 (13 reviews)
This Romanesque Revival building houses three floors of exhibits chronicling the Bluegrass region's rich heritage. Explore the preserved historic operating room and discover local artifacts spanning centuries.
See properties

What to do in Winchester

Lexington's Art Walk Tour

Lexington's Art Walk Tour

$40
per adult
Lexington's Art Walk Tour
See all activities in Winchester

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
$76 nightly
The price is $83 total per night from Jul 7 to Jul 8
$83 total
Jul 7 - Jul 8
Total with taxes and fees
7.2/10 Good! (818 reviews)
"Everything was good"

Reviewed on Jul 2, 2026

Baymont by Wyndham Winchester
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
$120 nightly
The price is $140 total per night from Jul 7 to Jul 8
$140 total
Jul 7 - Jul 8
Total with taxes and fees
8.4/10 Very Good! (734 reviews)
"The kids enjoyed the smore kits to use at the fire pits. The inside jacuzzi was lacking much need repairs and left our skin very irritated but the outdoor pool and jacuzzi was . Overall the property was nice and staff was very polite."

Reviewed on Jul 3, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $236 total per night from Jul 26 to Jul 27
$236 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (1,343 reviews)
"It was absolutely fabulous!"

Reviewed on Jul 6, 2026

The Manchester
See all 1,207 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 $883 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.