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.
Days Inn by Wyndham Frankfort

Days Inn by Wyndham Frankfort

2.5 out of 5
Price was CA $1,012, price is now CA $980 per person
CA $980
per person
May 14 - May 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
5.4/10 (738 reviews)
Mattress not comfortable, it was almost like sleeping on a foundation. Woke with new aches and did not sleep well.

Reviewed on Mar 27, 2026

Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was CA $1,237, price is now CA $1,123 per person
CA $1,123
per person
May 14 - May 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8.2/10 Very Good! (1,054 reviews)
The room was clean & beds comfortable, but very dated/worn; lighting thought needs replacing; outlet in bathroom was broken (did advise front desk; only stayed for one night which was fine) The lounge/bar was not open; hotel was in the mist of remodeling. Has potential of being grand but…

Reviewed on Mar 31, 2026

Comfort Inn & Suites Springfield

Comfort Inn & Suites Springfield

2 out of 5
Price was CA $1,124, price is now CA $1,080 per person
CA $1,080
per person
May 14 - May 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
6.8/10 (113 reviews)
The room was very clean and comfortable. The decor was very nice. The staff was welcoming and friendly. I would stay at this hotel again.

Reviewed on Jan 11, 2026

Bluegrass Inn

Bluegrass Inn

2 out of 5
Price was CA $1,051, price is now CA $1,050 per person
CA $1,050
per person
May 14 - May 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8/10 Very Good! (1,000 reviews)
Room was clean, outside was outdates as was inside but very clean and staff was friendly.

Reviewed on Apr 9, 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 $136 per night from May 3 to May 4
CA $136
CA $157 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (2,179 reviews)
Friendly staff and well stocked breakfast.

Reviewed on Apr 11, 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 $310 per night from Apr 26 to Apr 27
CA $310
CA $384 total
Apr 26 - Apr 27
includes taxes & fees
9.6/10 Exceptional! (1,229 reviews)
Breakfast and cocktails in the bar were excellent. The rooms are well appointed. My issue is that there is no room for your toiletries in the bathroom. We moved a table from the living room into the bathroom. The clean towels they store in the shower on the bench. We had to put them on the floor. ...

Reviewed on Apr 11, 2026

The Manchester
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Apr 26 to Apr 27
CA $113
CA $132 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (422 reviews)
Nice room, friendly staff,

Reviewed on Apr 11, 2026

Spark by Hilton Lexington Hamburg
See all 1,089 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

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
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
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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.