Winchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Nawa Aseen

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

3 out of 5
Price was CA $892, price is now CA $821 per person
CA $821
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.4/10 Very Good! (473 reviews)
Check in was easy and fast. The room is immediately comfortable and the staff was unbelievably kind.

Reviewed on Aug. 24, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,149, price is now CA $973 per person
CA $973
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Beautiful historic building. Big rooms, views. Fantastic shower and the robes are luxurious touch. Wonderful gallery. Extremely friendly staff.Stay here often.Live it!

Reviewed on Aug. 9, 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 CA $1,381, price is now CA $1,248 per person
CA $1,248
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
9.4/10 Exceptional! (820 reviews)
Like: The neighborhood and close dining. Breakfast was nice. Staff were awesome! Thank you. A little bit let down by the "spa shower".

Reviewed on Jul. 29, 2025

Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was CA $1,015, price is now CA $918 per person
CA $918
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (988 reviews)
Overall, the stay was okay. However, I had to go to the front desk several times about housekeeping. I requested daily housekeeping at check in but after about 4 days of no housekeeping had to go to the front desk to request that my trash and towels be changed. The sign in the bathroom says housekeeping every other day, so I was surprised that I went that long without housekeeping. Even when housekeeping did come, there were several times that the bed was not made.

Reviewed on Aug. 24, 2025

Rose Hill Inn

Rose Hill Inn

4 out of 5
Price was CA $1,127, price is now CA $1,038 per person
CA $1,038
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
10/10 Exceptional! (65 reviews)
The romantic cottage was just what we needed. Only thing we could possibly say we didn’t like was the entrance to the property off of the road. It was pretty tight, but thankfully it’s not too busy and we never had any issues with people coming or going at the same time that we were.

Reviewed on Jul. 29, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

Winchester Hotel Deals

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Sep 7 to Sep 8
CA $87
CA $101 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,655 reviews)
"Room was very largeand shower had good preasure and parking was no problem."

Reviewed on Aug. 23, 2025

Quality Inn Lexington -Horse Park
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Sep 14 to Sep 15
CA $157
CA $182 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Doubletree
"Towels were hard could have Ben soft fan in the room did not work as well but other than that it was clean and spacious"

Reviewed on Aug. 12, 2025

DoubleTree Suites by Hilton Hotel Lexington
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundable
The price is CA $89 per night from Aug 31 to Sep 1
CA $89
CA $103 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,324 reviews)
Reasonably priced convenient place to stay with no
"Relatively good value in a clean, quiet and convenient place to stay."

Reviewed on Aug. 21, 2025

GuestHouse Lexington
See all 1,128 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
The Kentucky Castle

The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

What to do in Winchester

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

CA $67
per adult
88% 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 $136
per adult
Lexington: Downtown Walking Food & History Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

CA $136
per adult
Distillery District Food & History Tour in Lexington
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 $821 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.