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.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was CA $1,014, price is now CA $945 per person
CA $945
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
The stay was enjoyable, the staff was very friendly and accomodating, the room could have been cleaner, there were stains and peeling paint on the ceiling in the bathroom, there was something that had run out of a vent on the bathroom wall leaving a white stain on the wall, the air conditioner unit was extremely loud when operating. Given the cost of the stay, I would expect these minor things to have been corrected prior the guest arrival.

Reviewed on Mar 16, 2026

The Aldenberg Hotel

The Aldenberg Hotel

2 out of 5
Price was CA $1,253, price is now CA $1,081 per person
CA $1,081
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
9.8/10 Exceptional! (6 reviews)
Room was clean. Staff was friendly and professional. Good location, walkable to restaurants and shops.

Reviewed on Feb 16, 2026

Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm

3 out of 5
Price was CA $1,085, price is now CA $1,024 per person
CA $1,024
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
9.4/10 Exceptional! (335 reviews)
Shops & restaurants nearby within walking distance.

Reviewed on Mar 12, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,043, price is now CA $985 per person
CA $985
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Very friendly staff. I felt so welcomed and cared for. Bedroom was very comfortable and great sizes. The bathroom has marble walls and floor and very spacious. It was a nice experience.

Reviewed on Mar 6, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was CA $1,032, price is now CA $977 per person
CA $977
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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 $120 per night from Mar 22 to Mar 23
CA $120
CA $140 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (2,189 reviews)
Room was very comfortable and clean.

Reviewed on Mar 15, 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 $251 per night from Apr 5 to Apr 6
CA $251
CA $316 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (1,196 reviews)
It was a very nice weekend. The hotel, the staff, the accommodations, the meals. The drinks were all top-notch.

Reviewed on Mar 16, 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 $122 per night from Mar 23 to Mar 24
CA $122
CA $142 total
Mar 23 - Mar 24
includes taxes & fees
9.4/10 Exceptional! (1,046 reviews)
I had a brief and great stay here! Everything was as it should be.

Reviewed on Mar 17, 2026

Elwood Hotel & Suites
See all 1,048 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(7 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
It's beginning to look a lot like Christmas.

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.