Midway Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Holiday Inn Express & Suites Lexington W - Versailles by IHG
CA $1,959
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Lexington (LEX)
9.4/10 Exceptional! (923 reviews)
Room was clean and comfortable. The staff was friendly and attentive, especially at breakfast. Have been here several times and have always had a good experience.
Reviewed on Aug 25, 2026
Home2 Suites by Hilton Lexington University / Medical Center
Zandale
CA $2,145
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Room was clean. Easy quick check in. Loved the large fridge with freezer
Reviewed on Aug 28, 2026
The Sire Hotel Lexington, Tapestry Collection by Hilton
Downtown Lexington
CA $2,831
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Windsor (YQG) to Lexington (LEX)
9.4/10 Exceptional! (900 reviews)
Great location in historic district
Safe, able to walk to restaurants, bars, and parks
Clean and quiet, friendly staff
Reviewed on Aug 25, 2026
Ready to book your vacation to Midway?
Midway Hotel Deals
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
CA $161
CA $187 total
Aug 31 - Sep 1
includes taxes & fees
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
CA $144
CA $194 total
Sep 6 - Sep 7
includes taxes & fees
8.4/10 Very good! (825 reviews)
"Everything was great"
Reviewed on Aug 25, 2026
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
CA $160
CA $192 total
Sep 20 - Sep 21
includes taxes & fees
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.
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.
What to do in Midway
Unique Horse Farm Tours with Insider Access to Private Farms
CA $82
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $137
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
CA $173
per adult
100% of travellers recommend
Frequently asked questions
How much does a Midway vacation package cost?
You'll find cheap prices from CA $1,959 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?
- 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.
- 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.
- 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.
- 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.
