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Midway Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Midway

Terrace/patio
Cozy cabin in the heart of horse country

Cozy cabin in the heart of horse country

Midway
10.0 out of 10, Exceptional, (31)
"This is a great property and was perfect for two couples. The house was clean and host was accessible if needed. We will definitely stay here again if in the area. Midway is a cute little town with several nice restaurants and shopping. "
United States
Tonya W.
Cozy cabin in the heart of horse country
Exterior
2 or 3 Bedroom/Baths House in Andover Convenient to All of Lexington

2 or 3 Bedroom/Baths House in Andover Convenient to All of Lexington

Lexington
10.0 out of 10, Exceptional, (306)
"House was great, clean and well stocked. Owner was amazing to work with, simple requirements and offered great suggestions, above and beyond! Would 100% recommend staying here! "
United States
Amanda R.
2 or 3 Bedroom/Baths House in Andover Convenient to All of Lexington
Smart TV
Bourbon on Broadway

Bourbon on Broadway

2.0 star property
Frankfort
9.8 out of 10, Exceptional, (18)
"We were in town to hit a few distilleries, so this place was perfect as is just a few minutes from Buffalo Trace! The apartment was so cute and had great character. We had 4 adults in our group so the space worked out wonderful for us.The beds were very comfortable. The kitchen was nicely stocked. "
United States
Ashley H.
The price is HK$777
HK$1,610 total
includes taxes & fees
16 Nov - 17 Nov
Bourbon on Broadway
Property grounds
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

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

Downtown Lexington
10.0 out of 10, Exceptional, (144)
"A lovely combination of historical charm with all the modern conveniences you need. And you can’t beat the location! Loved our stay."
United States
John T.
The price is HK$2,063
HK$3,667 total
includes taxes & fees
13 Nov - 14 Nov
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Terrace/patio
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

Frankfort
9.8 out of 10, Exceptional, (153)
"We enjoyed six comfortable days at this house. After spending all day on the Bourbon Trail, it was great to come back here and relax for the evening. Our host was attentive and gave us recommendations and information that made our stay enjoyable. "
United States
Patricia A.
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
Property grounds
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

Downtown Lexington
10.0 out of 10, Exceptional, (151)
"It was perfect, quaint, and clean!"
United States
Katie G.
The price is HK$770
HK$1,299 total
includes taxes & fees
16 Nov - 17 Nov
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Exterior
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28

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

Frankfort
10.0 out of 10, Exceptional, (15)
"Great place for a family vacation. Owners were very responsive. "
United States
Angela N.
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Exterior
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

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

Bagdad
9.6 out of 10, Exceptional, (238)
"This house was perfect for a ladies getaway.."
United States
Lisa B.
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Fridge, microwave, oven, stovetop
Location, Location, Location

Location, Location, Location

Northside District
9.2 out of 10, Wonderful, (65)
"We came to town to celebrate my daughter’s bday. Place was spacious, clean, an well stocked with everything we needed."
United States
Rachelle B.
The price is HK$855
HK$1,684 total
includes taxes & fees
19 Nov - 20 Nov
Location, Location, Location
Exterior
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

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

Frankfort
9.0 out of 10, Wonderful, (67)
"The beds were comfortable and everything was updated and clean. We enjoyed our stay!"
United States
Becky J.
The price is HK$466
HK$1,232 total
includes taxes & fees
16 Nov - 17 Nov
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Terrace/patio
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly

The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly

Lexington
10.0 out of 10, Exceptional, (17)
"We found this home perfect for our needs. Bedrooms all have large beds and TVs. Great space outside for the dog. Hot tub worked perfectly. Everything is a short drive away. We would pop downtown and back frequently between trips to distilleries. Half an hour to BT, WT, 4R,, etc. Hour to Bardstown and 1:15 back to Louisville. The neighborhood seemed very safe and quiet. Again, easy access everywhere. "
United States
Jason D.
The price is HK$1,133
HK$3,047 total
includes taxes & fees
19 Nov - 20 Nov
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
Exterior
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

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

Lexington
8.8 out of 10, Excellent, (38)
"The house was just as described and very clean. We would definitely stay again!"
United States
Dyone C.
The price is HK$653
HK$1,455 total
includes taxes & fees
13 Nov - 14 Nov
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop
Cecil's Cozy Cottage

Cecil's Cozy Cottage

Lexington
9.4 out of 10, Exceptional, (67)
"Property was describe very well and was very clean and comfortable. It was perfect for a visit with my daughter. Owners were super responsive and very easy to work with. Would definitely stay again when in the area."
United States
Christine W.
The price is HK$855
HK$1,702 total
includes taxes & fees
18 Nov - 19 Nov
Cecil's Cozy Cottage
Fridge, microwave, oven, stovetop
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.

This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.

2.0 star property
Downtown Lexington
10.0 out of 10, Exceptional, (14)
"We absolutely loved our stay! The property was super nice and very spacious, it was in a perfect location to reach anywhere in downtown Lex. Will definitely book again!"
United States
Anonymous traveller
The price is HK$1,554
HK$2,636 total
includes taxes & fees
16 Nov - 17 Nov
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
Interior
Solar Sanctuary

Solar Sanctuary

Chevy Chase
10.0 out of 10, Exceptional, (7)
"Great neighborhood "
United States
Michael T.
The price is HK$497
HK$1,199 total
includes taxes & fees
13 Nov - 14 Nov
Solar Sanctuary
Terrace/patio
Golf Simulator | Hot Tub | Game Room | Pool Table

Golf Simulator | Hot Tub | Game Room | Pool Table

Kenwick
10.0 out of 10, Exceptional, (65)
"This is a great place to stay. It was clean and well appointed and the property manager was prompt and helpful. "
United States
Amy B.
Golf Simulator | Hot Tub | Game Room | Pool Table
Exterior
Hot Tub/Playground/12 min to Horse Park/30min Ark

Hot Tub/Playground/12 min to Horse Park/30min Ark

Georgetown
10.0 out of 10, Exceptional, (23)
"Very nice house with everything you need for a night away"
United States
Tim S.
The price is HK$1,133
HK$2,886 total
includes taxes & fees
13 Nov - 14 Nov
Hot Tub/Playground/12 min to Horse Park/30min Ark
Exterior
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

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

Castlewood
9.6 out of 10, Exceptional, (81)
"This was a wonderful property with plenty of room. Very clean and beds were so comfortable. Will definitely stay here again. "
United States
Anonymous traveller
The price is HK$1,166
HK$2,944 total
includes taxes & fees
13 Nov - 14 Nov
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Private kitchen
Upscale 6 Bedroom Home Near Stadium and Restaurants

Upscale 6 Bedroom Home Near Stadium and Restaurants

Hollywood - Mt. Vernon
The price is HK$2,402
HK$6,280 total
includes taxes & fees
17 Nov - 18 Nov
Upscale 6 Bedroom Home Near Stadium and Restaurants
Fridge, microwave, oven, stovetop
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

Georgetown
10.0 out of 10, Exceptional, (31)
"Very nice property, private and quiet. Would definitely stay here again"
United States
Tina C.
The price is HK$1,360
HK$2,922 total
includes taxes & fees
13 Nov - 14 Nov
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
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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Top Midway Hotel Reviews

The Manchester

The Manchester

10/10 Excellent
"Well curated lobby and guest rooms"
Rob 1-night trip
Posted 16 hours ago
The Manchester

Find out more about Midway

Search for holiday rentals in Midway on Expedia! You can easily find your home rentals, villas, holiday apartments in Midway using one of the methods below:

  • View our selection of featured holiday rentals in Midway
  • Use the map to find apartments and other holiday homes in the Midway neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Midway while they last

Look no further and take a look at our great range of rental properties in Midway!

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?

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location: This holiday home rental outside of Midway is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Midway?

With 10 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 Masterson Station 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.