Winchester Vacation Packages

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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.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8.8/10 Excellent! (974 reviews)
Rooms were super spacious and every one of the staff members I came in contact with her top notch!

Reviewed on Jun. 30, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Wonderful hotel that used to be an old bank. Amazing room and amenities. Would definitely stay again.

Reviewed on Jul. 13, 2025

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
9.4/10 Exceptional! (95 reviews)
Absolutely amazing stay.

Reviewed on Jul. 14, 2025

Candlewood Suites Lexington by IHG

Candlewood Suites Lexington by IHG

2.5 out of 5
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8.6/10 Excellent! (507 reviews)
The hotel had a variety of kitchen appliances, such as crockpots, that you can use during your stay.

Reviewed on Jun. 1, 2025

Ready to book your vacation to Winchester?

 

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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
The price is CA $109 per night from Jul 23 to Jul 24
CA $109
CA $121 total
Jul 23 - Jul 24
includes taxes & fees
7/10 Good! (720 reviews)
"Quick stay after delayed flight. It had what we needed. Free breakfast that we were not expecting"

Reviewed on Jul. 4, 2025

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
The price is CA $92 per night from Aug 1 to Aug 2
CA $92
CA $107 total
Aug 1 - Aug 2
includes taxes & fees
8.8/10 Excellent! (57 reviews)
"Did not like the toilet paper, but everything else was great. David, at the front desk, is a treasure!!!"

Reviewed on Jul. 15, 2025

Spark by Hilton Lexington Hamburg
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Aug 15 to Aug 16
CA $191
CA $222 total
Aug 15 - Aug 16
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"Properrty is downtown. After sunset it us not a great neighborhood."

Reviewed on Jul. 12, 2025

Hilton Lexington/Downtown
See all 1,149 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Winchester

University of Kentucky

University of Kentucky

4.5/5(7 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
Fayette Mall

Fayette Mall

4.5/5(12 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
Eastern Kentucky University

Eastern Kentucky University

3.5/5(2 reviews)

Enjoy the collegiate vibe when you visit Eastern Kentucky University, during your travels in Richmond. While in this family-friendly area, you can savor the top-notch restaurants.

Eastern Kentucky University

What to do in Winchester

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

CA $41
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

CA $67
per adult
86% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

CA $135
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 can grab a vacation package to this top destination from CA $985 on Expedia. However, how much your vacation to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
December, January and February are the best times to look for cheap Winchester vacation packages. Travelling in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Winchester?
Generally, a handful of days is enough to see the main sights during your Winchester vacation. But if you prefer to have more time to kick back or go on day trips, think about extending your itinerary.
Is it worth booking a vacation package to Winchester?
During your Winchester vacation, you can count on experiencing some top-notch dining and nature. Leave enough time in your itinerary to check out leading sights like Bluegrass Heritage Museum and Lykins Park.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester getaway off to a flying start.
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 generally score a better deal than booking each component individually. And you'll still have the freedom to create a customized Winchester vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Winchester?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Winchester adventure.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred time of year and the activities available will also help you decide when to visit Winchester.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Winchester.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winchester. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Winchester vacation package.

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