Photo by Hyelsinta

Midway Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Midway

Cozy cabin in the heart of horse country
Terrace/patio

Cozy cabin in the heart of horse country

10.0 out of 10, Exceptional, (22)
"Host was very responsive and accommodating, cabin was in a great location, close to everything we were in town to do. It was clean and well stocked for our 5 night stay. "
Cozy cabin in the heart of horse country
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Exterior

Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28

9.8 out of 10, Exceptional, (8)
"Everything about our stay was great. The place itself is fantastic and the owner's communication the entire time was top of the line. Would recommend to anyone"
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Carriage on Petticoat
Terrace/patio

Carriage on Petticoat

2.0 star property
10.0 out of 10, Exceptional, (22)
"Nice place, good host and great location. I would stay here again."
The price is HK$1,177
HK$2,602 total
includes taxes & fees
10 Aug - 11 Aug
Carriage on Petticoat
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Fridge, coffee/tea maker, cookware/dishes/utensils

This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.

9.2 out of 10, Wonderful, (66)
"Everything was exquisite!!! Clean, Inviting and cozy!!!"
The price is HK$1,138
HK$2,033 total
includes taxes & fees
11 Aug - 12 Aug
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Exterior

Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

9.6 out of 10, Exceptional, (228)
"This house was perfect for a ladies getaway.."
The price is HK$2,169
HK$3,951 total
includes taxes & fees
13 Aug - 14 Aug
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Property grounds

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

10.0 out of 10, Exceptional, (273)
"Peaceful, relaxing, really enjoyed it"
The price is HK$1,060
HK$1,886 total
includes taxes & fees
18 Aug - 19 Aug
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Location, Location, Location
TV

Location, Location, Location

9.2 out of 10, Wonderful, (57)
"My week stay was great! Hosts were flexible and accommodated a reservation change to add two additional days. Would highly recommend for anyone staying in Lexington!"
The price is HK$863
HK$1,674 total
includes taxes & fees
10 Aug - 11 Aug
Location, Location, Location
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

9.6 out of 10, Exceptional, (76)
"We had a great stay. Perfect for multigenerational families."
The price is HK$1,476
HK$3,362 total
includes taxes & fees
2 Sept - 3 Sept
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!
Property grounds

KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

9.8 out of 10, Exceptional, (118)
"Was a very nice cottage, would definitely recommend to others"
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Exterior

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

8.8 out of 10, Excellent, (55)
"The property was nice and felt cozy the entire stay"
The price is HK$471
HK$1,244 total
includes taxes & fees
3 Sept - 4 Sept
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Golden House: Sleeps 12 • Cozy + Modern - close to UK, Summit + Keeneland!
Interior

Golden House: Sleeps 12 • Cozy + Modern - close to UK, Summit + Keeneland!

10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our stay at Golden House. From the well equipped kitchen to the lovely sitting room to the fun basement, all was just as described or better!"
Golden House: Sleeps 12 • Cozy + Modern - close to UK, Summit + Keeneland!
Sleeps18|7500SqFt|Themed Spaces|Bourbon Trial|Hot Tub|Creek|Sauna|Lux Amenties
Interior

Sleeps18|7500SqFt|Themed Spaces|Bourbon Trial|Hot Tub|Creek|Sauna|Lux Amenties

9.6 out of 10, Exceptional, (5)
Sleeps18|7500SqFt|Themed Spaces|Bourbon Trial|Hot Tub|Creek|Sauna|Lux Amenties
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

9.0 out of 10, Wonderful, (29)
"The house was just as described and very clean. We would definitely stay again!"
The price is HK$699
HK$1,509 total
includes taxes & fees
11 Aug - 12 Aug
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
💙Modern Downtown with Parking - Keeneland - Horse Park
Outdoor dining

💙Modern Downtown with Parking - Keeneland - Horse Park

9.6 out of 10, Exceptional, (19)
"Enjoyed our stay. Location was great. "
The price is HK$1,095
HK$2,419 total
includes taxes & fees
10 Aug - 11 Aug
💙Modern Downtown with Parking - Keeneland - Horse Park
Modern cottage located in the heart of the Bourbon Trail
Fridge, microwave, oven, stovetop

Modern cottage located in the heart of the Bourbon Trail

9.8 out of 10, Exceptional, (24)
"Very clean and great condition. Would stay again for sure. "
The price is HK$981
HK$1,722 total
includes taxes & fees
18 Aug - 19 Aug
Modern cottage located in the heart of the Bourbon Trail
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Property grounds

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

8.6 out of 10, Excellent, (33)
"Walk anywhere! It is a great location in Frankfort. "
The price is HK$589
HK$1,362 total
includes taxes & fees
12 Aug - 13 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Property grounds

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

10.0 out of 10, Exceptional, (137)
"A lovely combination of historical charm with all the modern conveniences you need. And you can’t beat the location! Loved our stay."
The price is HK$2,084
HK$3,703 total
includes taxes & fees
8 Aug - 9 Aug
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Luxurious 1-bedroom with Free Parking
Exterior

Luxurious 1-bedroom with Free Parking

9.8 out of 10, Exceptional, (42)
"Nicely upgraded unit, relaxing and comfortable. Close to everything!"
The price is HK$699
HK$1,905 total
includes taxes & fees
13 Aug - 14 Aug
Luxurious 1-bedroom with Free Parking
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

9.4 out of 10, Exceptional, (58)
"Super location, amenities, very clean, fenced yard for our dog was a definite bonus. Would rent again for sure!"
The price is HK$903
HK$1,731 total
includes taxes & fees
27 Aug - 28 Aug
This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Peaceful Retreat on the Bourbon Trail
Interior

Peaceful Retreat on the Bourbon Trail

9.6 out of 10, Exceptional, (4)
"The yard is huge and safe from the quiet road -- perfect for pets and kids, especially with the overlooking front deck. The gorgeous home was well-stocked with everything from bedsheets to fly swatters. The experience perfectly fit what I was looking for: a peaceful Kentucky stay for my adventurous feline companion (and human partner, too)."
The price is HK$1,130
HK$2,103 total
includes taxes & fees
8 Aug - 9 Aug
Peaceful Retreat on the Bourbon Trail
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Midway Hotel Reviews

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent
"This was a very nice hotel with friendly and helpful staff. It was clean and everything looked rather new. Nice breakfast options."
Jeff 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Frequently asked questions

Can I find a holiday rental in Midway?

Yes, there are holiday rentals close to the most popular sights in Midway, or you can select a more secluded option if you're looking for a relaxing stay. Midway is known for its wineries and local tours. Make sure you have time to check out the art while you're in the area.

What are some of the best holiday rentals that Midway has to offer?

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.: This holiday home rental outside of Midway is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Midway?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Midway stay.

What’s there to see and do in Midway?

While exploring the area, visit family-friendly sights like Blue Grass Railroad Museum, or get outside and enjoy nature at Kentucky Horse Park. Equus Run Vineyard & Winery and Damselfly Gallery are other places to visit while you're in town.

What’s a holiday rental in Midway like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Midway. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family getaway.