Winchester Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Winchester Vacation Packages

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
The price is ￥11,763 per night from Aug 10 to Aug 11
￥11,763
￥12,968 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (731 reviews)
"The staff was exceptionally friendly and the hotel, room and pool were very clean. But, the bed that we had was hard and pillows were lumpy and very uncomfortable."

Reviewed on Jul 28, 2025

Baymont by Wyndham Winchester
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is ￥8,697 per night from Aug 4 to Aug 5
￥8,697
￥9,587 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very Good! (84 reviews)
"Nice clean place"

Reviewed on Jul 13, 2025

Value Stay
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is ￥13,779 per night from Aug 24 to Aug 25
￥13,779
￥15,993 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (2,250 reviews)
"Great hotel!"

Reviewed on Jul 30, 2025

GLō Best Western Lexington
See all 1,147 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.

Discover the most popular places to visit in Winchester

Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(328 reviews)

Explore Kentucky Horse Park, a favorite green space in Lexington, and also enjoy the area's horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

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

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

￥4,396
per traveler
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

￥1,477
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

￥14,512
per adult
Lexington: Downtown Walking Food & History Tour
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices 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. Traveling in quieter months means you can generally find better prices on accommodations and flights.
How many days is enough for Winchester?
With a well-organized travel plan, you can easily visit the most popular Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester vacation for longer.
Is it worth booking a vacation package to Winchester?
Known for its dining, nature and plenty of other highlights, you can be certain Winchester is a good vacation destination. Some of the most popular attractions to add to your itinerary? Don't miss Bluegrass Heritage Museum and Lykins Park during your Winchester vacation.
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.
How to plan a trip to Winchester?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Winchester.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Winchester.
  3. Decide how long to go away for: Now that you know more about Winchester, you can work out the right length of your vacation. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, lock in the ideal Winchester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.