Midway Vacation Packages

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Your Midway Vacation

Reserve a Midway vacation package and get ready to experience everything this city has to offer. Consider basing yourself in the neighborhood of Northside District, which is great for bars and pubs, history and dining. If taking in sights is on the cards during your trip to Midway, look around leading attractions like Equus Run Vineyard & Winery, Headley-Whitney Museum and Damselfly Gallery. Stop daydreaming and start doing. Check out the wide range of options on Expedia today and put your Midway vacation plans into action!

Top Midway Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was CA $1,015, price is now CA $960 per person
CA $960
per person
Jan 4 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
7.8/10 Good! (1,040 reviews)
We did not ask for our room to be cleaned/new towels but it was anyway. That was nice. This sink remained clogged so probably needs a more extensive fix. The windows are very thin. We could hear people speaking in the street six levels down. Beds are hard as rocks and this usually isn't a problem. Please discount the rate for themissing so many items right now. PS plain refrigerators are NOT mini bars!

Reviewed on Nov 6, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,060, price is now CA $1,010 per person
CA $1,010
per person
Jan 4 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,005 reviews)
Loved the art gallery

Reviewed on Nov 7, 2026

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was CA $1,019, price is now CA $987 per person
CA $987
per person
Jan 4 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (1,004 reviews)

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was CA $1,000, price is now CA $971 per person
CA $971
per person
Jan 4 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.6/10 Exceptional! (1,177 reviews)

Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was CA $985, price is now CA $962 per person
CA $962
per person
Jan 4 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)

Ready to book your vacation to Midway?

 

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Midway Hotel Deals

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $73 per night from Nov 30 to Dec 1
CA $73
CA $84 total
Nov 30 - Dec 1
includes taxes & fees
8.2/10 Very good! (1,521 reviews)
"Nunca limpiaron el cuarto, no sé si había que pedirlo"

Reviewed on Nov 5, 2026

Quality Inn Lexington -Horse Park
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Fully refundable
The price is CA $100 per night from Nov 9 to Nov 10
CA $100
CA $116 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very good! (1,727 reviews)
"The room was clean with plenty of space to stretch out. We were there for a quick overnight stay. It was quiet and we were able to rest for the next part of our trip."

Reviewed on Nov 7, 2026

GuestHouse Lexington
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Dec 1 to Dec 2
CA $171
CA $206 total
Dec 1 - Dec 2
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Loved the art gallery"

Reviewed on Nov 7, 2026

21c Museum Hotel Lexington
See all 1,100 properties in Midway
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.
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Stay near popular Midway attractions

Equus Run Vineyard & Winery

8.0/10 (1 review)
You can enjoy a tasting or tour at Equus Run Vineyard & Winery during your travels to Midway. Attend a sporting event or simply enjoy the lively bars while you're in the area.
See properties

What to do in Midway

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

CA $83
per adult
90% 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 $140
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

CA $177
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
See all activities in Midway

Frequently asked questions

How much does a Midway vacation package cost?
You'll find cheap prices from CA $960 on Expedia for your Midway getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Midway costs.
What are the cheapest months to go to Midway?
To pick up cheap Midway vacation packages, plan your getaway outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Midway?
Generally, a handful of days is enough to tick off the top attractions during your Midway vacation. But if you want to have some time to rest or take day tours, think about extending your itinerary.
How to find the best Midway package deals?
Use Expedia's handy filters to help you find some great Midway package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Midway package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Midway vacation as a package?
You can enjoy significant savings on your Midway escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Midway?
If you've got your Midway vacation dates locked in, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Midway?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred season and the available activities will also help you decide when to escape to Midway.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Midway.
  3. Determine how many days away: Start by making a list of all the attractions you want to experience in Midway. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Midway 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.