Midway Vacation Packages 2026 from $484

Midway flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Sweet Victory Bed and Breakfast

$484

per person

Oct 9 - Oct 12

found 20 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi in public areas. A communal living room, a picnic area, and dry cleaning are also on offer.

The Delegate

$610

per person

Oct 15 - Oct 18

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and express check-out are also offered on site.

Holiday Inn Express & Suites Lexington W - Versailles by IHG

$647

per person

Oct 15 - Oct 18

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

The Sire Hotel Lexington, Tapestry Collection by Hilton

Downtown Lexington

$1,104

per person

Oct 15 - Oct 17

found 4 hours ago

Roundtrip flight included

New York (LGA) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a terrace are also offered.

The Ashbrook Hotel

$757

per person

Oct 15 - Oct 18

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a picnic area, and express check-out are also offered.

Top Midway hotels deals

Hyatt Regency Lexington

401 W High St Lexington KY

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$157 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Free airport shuttle

Marriott Lexington Griffin Gate Golf Resort & Spa

1800 Newtown Pike Lexington KY

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$149 total

Sep 20 - Sep 21

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the indoor pool and perks like free self parking.

Pool

Hot Tub

The Manchester

941 Manchester St Lexington KY

$246 nightly

$285 total

Sep 29 - Sep 30

Total with taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, express check-in, and express check-out are also offered.

21c Museum Hotel Lexington

167 West Main Street Lexington KY

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$172 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

Holiday Inn Express Lexington - Horse Park Area by IHG

1935 Stanton Way, 1935 4 yes Lexington KY

Free Cancellation

$103 nightly

$120 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a snack bar/deli, and express check-in are also on offer.

Pool

Breakfast included

DoubleTree Suites by Hilton Hotel Lexington

2601 Richmond Rd Lexington KY

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$142 total

Sep 20 - Sep 21

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. Self parking, a business center, and a coffee shop are also offered.

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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.

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.

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Frequently asked questions

How much are vacation packages to Midway?

Prepare to be pleasantly surprised — you can unwind in Midway for as little as $484. Here at Travelocity, we save you money and time with our excellent vacation packages. With hotels, flights and tours all ready to go at our one-stop shop, why wait any longer?

Where can I get the best vacation package deals for Midway?

For the best Midway package deal, book with Travelocity. Take your pick of 400 airlines and 1,000,000 properties around the globe to create the ultimate trip — it couldn't be easier than that.

Why should I purchase my Midway vacation package with Travelocity?

Whether you're searching for the ultimate unplugged vacation or you crave the fun and excitement of a towering metropolis, booking everything with Travelocity saves you time, hassle and money. No need to comb through hundreds of websites for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our professional customer service experts are available 24/7 should you need anything at all.

Can I save money on my Midway car rental if I combine it with my hotel or flight?

You most certainly can — bundle your flight, hotel and car into a Midway vacation package and you'll save a ton. With so much to discover in Midway, having your own ride will more than come in handy. Once you're in the driver's seat, turn up the tunes and find your way to Churchill Downs, a well-known sight about 60 mi from Midway.

Which airport is best for Midway?

Midway has two main airports to select from — Louisville Intl. Airport (SDF) (60 mi away from the city center) and Blue Grass Airport (LEX) (9 mi away from central Midway).

What is there to do in Midway?

While venturing off the beaten track is rewarding, you shouldn't miss the well-known sights that make a destination famous. Equus Run Vineyard & Winery and Damselfly Gallery are just two of them in Midway.

Where should I stay when visiting Midway?

Many people opt to hit the hay at the Midway Home on 22 Acres Near Bourbon Trail!. It's sure to be a good base for your Midway escape.