Midway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, 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.
Sleep Inn

Sleep Inn

2.5 out of 5
Price was CA $910, price is now CA $895 per person
CA $895
per person
Aug 14 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.2/10 Very Good! (662 reviews)
The Sleep Inn was a great choice. Nice, clean, updated.

Reviewed on Jun 1, 2026

Best Western Plus Georgetown Corporate Center Hotel

Best Western Plus Georgetown Corporate Center Hotel

2.5 out of 5
Price was CA $971, price is now CA $937 per person
CA $937
per person
Aug 14 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
8.6/10 Excellent! (1,002 reviews)
Could use some updates but overall a nice place to stay.

Reviewed on Jun 2, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,214, price is now CA $1,062 per person
CA $1,062
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Loved the restroom. So clean and roomy and comfortable. Room very clean.

Reviewed on May 26, 2026

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was CA $1,217, price is now CA $1,094 per person
CA $1,094
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Lexington (LEX)
9.4/10 Exceptional! (107 reviews)
We were doing a cross country trip in our airstream. We stayed one night at the BnB and absolutely loved the grounds, our room, and our host. She went above and beyond accommodating our airstream and our dogs.

Reviewed on May 11, 2026

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
Price was CA $1,354, price is now CA $1,225 per person
CA $1,225
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Lexington (LEX)
9.4/10 Exceptional! (2,207 reviews)
Hotel staff were great, the rooms were clean And the price was reasonable. Would definitely stay again.

Reviewed on Jun 3, 2026

Ready to book your vacation to Midway?

 

Choose your dates

Midway Hotel Deals

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Jun 14 to Jun 15
CA $136
CA $158 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (1,163 reviews)
"Comfortable, quick check in, clean hotel"

Reviewed on Jun 2, 2026

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Jul 1 to Jul 2
CA $242
CA $305 total
Jul 1 - Jul 2
includes taxes & fees
9.6/10 Exceptional! (1,308 reviews)
"Great valet workers"

Reviewed on Jun 3, 2026

The Manchester
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 $159 per night from Jun 28 to Jun 29
CA $159
CA $184 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Clean and staff was very helpful."

Reviewed on Jun 4, 2026

DoubleTree Suites by Hilton Hotel Lexington
See all 1,086 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Midway

Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky

University of Kentucky

4.5/5(8 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
0_130598195

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
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

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 $81
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington's Art Walk Tour

Lexington's Art Walk Tour

CA $55
per adult
Lexington's Art Walk Tour
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 Midway

Explore a world of travel with Expedia

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