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 $1,189, price is now CA $1,065 per person
CA $1,065
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.2/10 Very Good! (1,053 reviews)
Room was good and clean. Check in was easy and staff friendly. Breakfast was actually good for a free buffet. The hotel is under construction, so a little messy and not complete. But, still good stay only 1.1 miles from Buffalo Trace

Reviewed on Mar 13, 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 $1,938, price is now CA $1,765 per person
CA $1,765
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (2,211 reviews)
Everything was fine.

Reviewed on Mar 12, 2026

GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was CA $1,306, price is now CA $1,196 per person
CA $1,196
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.4/10 Very Good! (1,562 reviews)
Finish the updates. Noisy. No place to lay toiletries in bathroom.

Reviewed on Mar 14, 2026

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
Price was CA $1,853, price is now CA $1,699 per person
CA $1,699
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Lexington (LEX)
8.6/10 Excellent! (1,005 reviews)
This hotel was clean and staff members were friendly. The bed and pillows were comfortable and the shower was hot. The complimentary breakfast was wonderful.

Reviewed on Mar 14, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was CA $1,417, price is now CA $1,315 per person
CA $1,315
per person
May 8 - May 10
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Lexington (LEX)
9.4/10 Exceptional! (1,038 reviews)
Nice stay- highly recommend

Reviewed on Mar 14, 2026

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Midway Hotel Deals

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 $92 per night from Mar 17 to Mar 18
CA $92
CA $107 total
Mar 17 - Mar 18
includes taxes & fees
9.4/10 Exceptional! (2,187 reviews)
Pillows were very long and hard, and no cups in room to use. Otherwise great room and clean.

Reviewed on Mar 14, 2026

Holiday Inn Express Lexington Horse Park Area by IHG
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Apr 5 to Apr 6
CA $252
CA $317 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (1,193 reviews)
We were upgraded to a corner double queen suite. The staff is always wonderful. Very convenient walk to Manchester Music Hall next door.

Reviewed on Mar 11, 2026

The Manchester
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
444 Parkway Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Mar 22 to Mar 23
CA $134
CA $156 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (1,044 reviews)
Nice stay- highly recommend

Reviewed on Mar 14, 2026

Elwood Hotel & Suites
See all 1,050 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
It's beginning to look a lot like Christmas.

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 $136
per adult
Lexington: Downtown Walking Food & History Tour
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

CA $144
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.