Winchester Vacations from $302

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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.
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Price was $346, price is now $302 per person
$302
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
8/10 Very Good! (1,013 reviews)
The hotel was close to I-75 which made for easy commuting.

Reviewed on Nov 9, 2025

Hampton Inn Richmond

Hampton Inn Richmond

2.5 out of 5
Price was $377, price is now $316 per person
$316
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.2/10 Wonderful! (1,004 reviews)
Even though they were in the middle of a remodel our stay was great. Staff was friendly and effecient. Room was clean and comfortable. Morning breakfast was also very good with lots of hot food choices

Reviewed on Nov 7, 2025

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was $418, price is now $365 per person
$365
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
8.2/10 Very Good! (1,007 reviews)
Staff were great. Room was clean and comfortable. On site restaurant had great options. Welcoming fire going in the foyer fireplace.

Reviewed on Nov 8, 2025

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $428, price is now $375 per person
$375
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (831 reviews)
We had a very nice stay

Reviewed on Nov 3, 2025

Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

3.5 out of 5
Price was $462, price is now $405 per person
$405
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (1,003 reviews)
Our lights in the room didn’t work nor did outlets.

Reviewed on Oct 19, 2025

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Discover the most popular places to visit in Winchester

Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(328 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
In a hores eye #2

University of Kentucky

4.5/5(384 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
It's beginning to look a lot like Christmas.

Fayette Mall

4.5/5(321 reviews)

You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.

Fayette Mall

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
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

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $89 total per night from Nov 17 to Nov 18
$89 total
Nov 17 - Nov 18
Total with taxes and fees
8.4/10 Very Good! (994 reviews)
Lots of healthy choices

Reviewed on Nov 7, 2025

Best Western Winchester Hotel
Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

2 out of 5
750 Newtown Court, Lexington, KY
Fully refundable
$51 nightly
The price is $60 total per night from Nov 23 to Nov 24
$60 total
Nov 23 - Nov 24
Total with taxes and fees
5.8/10 (1,008 reviews)
The rooms and the front offfice were very clean. The staff were all so friendly. Its very centrally located.

Reviewed on Nov 7, 2025

Motel 6 Lexington, KY - Airport
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $142 total per night from Nov 30 to Dec 1
$142 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
Good

Reviewed on Nov 9, 2025

Hilton Lexington/Downtown
See all 1,169 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 $302 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.