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 $882, price is now CA $818 per person
CA $818
per person
Sep 10 - Sep 12
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Lexington (LEX)
8.2/10 Very good! (1,059 reviews)
Parking was safe an easy. Everything was great, but the hotel is under renovation and can’t give 5 stars due to that fac.

Reviewed on Jul 4, 2026

The Delegate

The Delegate

3.5 out of 5
Price was CA $993, price is now CA $966 per person
CA $966
per person
Sep 10 - Sep 12
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Lexington (LEX)
9.2/10 Wonderful! (462 reviews)
Had a room above the restaurant and was very loud. Could hear ever

Reviewed on Jun 29, 2026

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Midway Hotel Deals

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
The price is CA $147 per night from Jul 7 to Jul 8
CA $147
CA $198 total
Jul 7 - Jul 8
includes taxes & fees
8.4/10 Very good! (732 reviews)
"The kids enjoyed the smore kits to use at the fire pits. The inside jacuzzi was lacking much need repairs and left our skin very irritated but the outdoor pool and jacuzzi was . Overall the property was nice and staff was very polite."

Reviewed on Jul 3, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Jul 26 to Jul 27
CA $267
CA $335 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (1,341 reviews)
"Such a great hotel experience. The staff - from desk host to valet guys - were all so friendly and helpful. The restaurant and bar were both so excellent. The room and bed made us feel like we were staying at home."

Reviewed on Jul 5, 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 $158 per night from Jul 19 to Jul 20
CA $158
CA $183 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"The hotel was a nice hotel and unique with its design of interior rooms with balconies. It had a charming Kentucky feel. The issue was the cleaning of the room. We checked in on Thursday and had to extend our stay, upon check in, until Sunday. After the first night, our room was not cleaned and when ..."

Reviewed on Jun 29, 2026

DoubleTree Suites by Hilton Hotel Lexington
See all 1,087 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
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Stay near popular Midway attractions

Equus Run Vineyard & Winery

8.0/10 (1 review)
You can enjoy a tasting or tour at Equus Run Vineyard & Winery during your travels to Midway. Attend a sporting event or simply enjoy the lively bars while you're in the area.
See properties

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 $82
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 $137
per adult
100% of travellers recommend
Lexington: Downtown Walking Food & History Tour
See all activities in Midway

Frequently asked questions

How much does a Midway vacation package cost?
You'll find cheap prices from CA $818 on Expedia for your Midway getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Midway costs.
What are the cheapest months to go to Midway?
To pick up cheap Midway vacation packages, plan your getaway outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Midway?
Generally, a handful of days is enough to tick off the top attractions during your Midway vacation. But if you want to have some time to rest or take day tours, think about extending your itinerary.
How to find the best Midway package deals?
Use Expedia's handy filters to help you find some great Midway package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Midway package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Midway vacation as a package?
You can enjoy significant savings on your Midway escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Midway?
If you've got your Midway vacation dates locked in, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Midway?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred season and the available activities will also help you decide when to escape to Midway.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Midway.
  3. Determine how many days away: Start by making a list of all the attractions you want to experience in Midway. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Midway vacation package for you.

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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.