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.
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was CA $824, price is now CA $779 per person
CA $779
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.4/10 Very Good! (1,590 reviews)
Great staff clean rooms breakfast Could of been better

Reviewed on May 12, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $971, price is now CA $870 per person
CA $870
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Awesome location with tons of artistic charm.

Reviewed on May 6, 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 $1,012, price is now CA $943 per person
CA $943
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (2,196 reviews)
Traveling with a "service dog" the employee referred to her as a "service pet" which caused both my husband and I to laugh, however knowing the laws regarding service animals is appreciated.

Reviewed on May 11, 2026

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 $1,036, price is now CA $966 per person
CA $966
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (882 reviews)
Liked the courtyard area and the deck.

Reviewed on May 11, 2026

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was CA $933, price is now CA $875 per person
CA $875
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Atrium was beautiful- rooms large and little balcony was adorable! The shower was huge!

Reviewed on May 11, 2026

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Midway Hotel Deals

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from May 26 to May 27
CA $251
CA $315 total
May 26 - May 27
includes taxes & fees
9.6/10 Exceptional! (1,279 reviews)
Exceeded expectations

Reviewed on May 11, 2026

The Manchester
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is CA $142 per night from May 17 to May 18
CA $142
CA $165 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (2,187 reviews)
Pleased with rooms. Decent breakfast. Friendly staff.

Reviewed on May 11, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
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 $208 per night from Jun 1 to Jun 2
CA $208
CA $242 total
Jun 1 - Jun 2
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Room was clean and comfy and had everything you needed.

Reviewed on May 11, 2026

Hilton Lexington/Downtown
See all 1,084 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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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

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

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
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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 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: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

CA $137
per adult
Lexington: Downtown Walking Food & History Tour
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

CA $145
per adult
Bites of the Bluegrass Cocktails & Bites Tour
See all activities in Midway

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