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Midway Holiday Rentals

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Midway holiday rentals

Fridge, microwave, oven, stovetop
Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Book now for a perfect stay!

Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Book now for a perfect stay!

Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Book now for a perfect stay!
2.0 star property
Midway
10.0 out of 10, Exceptional, (2)
"We had the most amazing time at FarRhode! The owners thought of everything. The place is so beautiful and well stocked with everything you could need. The view from any window is stunning and the star gazing off the deck at night was spectacular. We saw cows, horses, geese, a skunk and “Bobby” the donkey. The location is perfect for the bourbon trail and Keeneland. We will definitely be renting again!"
United States
Stephanie P.
The price is HK$2,019
HK$3,665 total
includes taxes & fees
29 Dec - 30 Dec
Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Book now for a perfect stay!
Smart TV, fireplace, books
Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (38)
"Staying in the Caboose on the Farm was such a fun and relaxing escape. The space was clean, cozy and full of charm with beautiful views and friendly animals. It was the perfect mix of comfort and nature. Highly recommend for anyone looking for a unique getaway!"
United States
Lindsey
The price is HK$1,102
HK$1,818 total
includes taxes & fees
26 Jan - 27 Jan 2026
Bourbon Trail: Caboose on the Farm
Fridge, microwave, oven, stovetop
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

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

This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
2.0 star property
Downtown Lexington
9.4 out of 10, Exceptional, (13)
"Great location and huge place. Gorg windows and high ceilings. I stayed here for a friends wedding and loved it. Will stay again next time I’m in town! "
United States
Londyn
The price is HK$894
HK$1,696 total
includes taxes & fees
29 Dec - 30 Dec
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior detail
Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK

Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK

Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK
2.0 star property
Downtown Lexington
10.0 out of 10, Exceptional, (7)
"This place is super cute, very well maintained, and is easily accessible. The host was friendly and quick to respond to any messages sent. I would 100% stay here again when coming back to Lexington!"
United States
Chelsey G.
Safe & Secure 2br near UKPD in Lex - Rest easy, walk 2 UK
Property grounds
Treetops Solar Sanctuary

Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (84)
"Great location in beautiful neighborhood! "
United States
Tiffany S.
The price is HK$420
HK$1,155 total
includes taxes & fees
28 Dec - 29 Dec
Treetops Solar Sanctuary
2 bedrooms, desk, iron/ironing board, travel cot
175 LEX - Spacious Two Bedroom Downtown Lexington

175 LEX - Spacious Two Bedroom Downtown Lexington

175 LEX - Spacious Two Bedroom Downtown Lexington
Downtown Lexington
9.6 out of 10, Exceptional, (33)
"Location, location, location! Great views of Main Street from the bedrooms and living rooms."
United States
Fisher S.
The price is HK$972
HK$1,924 total
includes taxes & fees
11 Jan - 12 Jan 2026
175 LEX - Spacious Two Bedroom Downtown Lexington
Fridge, microwave, oven, stovetop
My Old Kentucky Home

My Old Kentucky Home

My Old Kentucky Home
Lexington
10.0 out of 10, Exceptional, (27)
"Cool property, with a great location. Owner had great communication."
United States
Anonymous traveller
The price is HK$607
HK$1,922 total
includes taxes & fees
29 Dec - 30 Dec
My Old Kentucky Home
Interior
175 LEX - Spacious Two Bedroom - Near Rupp Arena!

175 LEX - Spacious Two Bedroom - Near Rupp Arena!

175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Downtown Lexington
9.6 out of 10, Exceptional, (16)
"Great location, easy access to all things downtown"
United States
Alex
The price is HK$894
HK$1,795 total
includes taxes & fees
28 Dec - 29 Dec
175 LEX - Spacious Two Bedroom - Near Rupp Arena!
Interior
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Frankfort
8.8 out of 10, Excellent, (97)
"We enjoyed our stay while we were down for Breyer Fest. It was close to places we wanted to go and quiet. We would definitely stay here again."
United States
Jacob Y.
The price is HK$544
HK$1,281 total
includes taxes & fees
28 Dec - 29 Dec
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Exterior
2BD 2Bath, Ideally Located Cottage

2BD 2Bath, Ideally Located Cottage

2BD 2Bath, Ideally Located Cottage
Frankfort
9.8 out of 10, Exceptional, (48)
"Cute house with everything we needed during our stay!"
United States
Debra R.
The price is HK$778
HK$2,507 total
includes taxes & fees
4 Jan - 5 Jan 2026
2BD 2Bath, Ideally Located Cottage
Exterior detail
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Lawrenceburg
10.0 out of 10, Exceptional, (121)
"This property was the perfect place to come back to and unwind after funfilled days on the bourbon trail!"
United States
Ashley C.
The price is HK$994
HK$1,627 total
includes taxes & fees
28 Dec - 29 Dec
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Property grounds
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Downtown Lexington
9.8 out of 10, Exceptional, (105)
"Worked perfectly for our budget and location"
United States
Kyle I.
The price is HK$833
HK$1,598 total
includes taxes & fees
28 Dec - 29 Dec
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Exterior
Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.2 out of 10, Wonderful, (10)
"The property was clean and well kept, the location is perfect and communication was immediate. I will definitely rent again!"
United States
Becky S.
The price is HK$497
HK$1,705 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 1-bedroom in Lexington
Exterior
Capital City Cottage

Capital City Cottage

Capital City Cottage
Frankfort
8.6 out of 10, Excellent, (43)
"A cozy cottage nestled in the mountain that felt like home away from home. "
United States
Jena B.
The price is HK$778
HK$1,912 total
includes taxes & fees
7 Jan - 8 Jan 2026
Capital City Cottage
Exterior
Lexington Apt. with parking & private entrance Preview listing

Lexington Apt. with parking & private entrance Preview listing

Lexington Apt. with parking & private entrance Preview listing
Copperfield
10.0 out of 10, Exceptional, (139)
"The apartment is very nice and comfortable. Check in was a breeze. Will stay again if available. "
United States
Beverly C.
The price is HK$622
HK$1,263 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lexington Apt. with parking & private entrance Preview listing
Smart TV
Bourbon on Broadway

Bourbon on Broadway

Bourbon on Broadway
2.0 star property
Frankfort
10.0 out of 10, Exceptional, (22)
" wanted to visit. Just a nice place to stay big enough for taking Really enjoyed it. "
United States
Anonymous traveller
The price is HK$1,050
HK$1,955 total
includes taxes & fees
4 Jan - 5 Jan 2026
Bourbon on Broadway
1 bedroom, iron/ironing board, travel cot, free WiFi
175 LEX - Stunning Downtown Views on Main Street!

175 LEX - Stunning Downtown Views on Main Street!

175 LEX - Stunning Downtown Views on Main Street!
Downtown Lexington
9.8 out of 10, Exceptional, (44)
"Very clean and convenient to Rupp arena "
United States
Randy R.
175 LEX - Stunning Downtown Views on Main Street!
Fridge, microwave, oven, stovetop
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.

3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.

3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Frankfort
10.0 out of 10, Exceptional, (31)
"Great spot to rest and recuperate after a long day on the Bourbon trail!"
United States
Jonathan F.
The price is HK$1,113
HK$2,285 total
includes taxes & fees
28 Dec - 29 Dec
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Interior
Springside Bourbon Getaway

Springside Bourbon Getaway

Springside Bourbon Getaway
Georgetown
10.0 out of 10, Exceptional, (28)
"Lovely, just right for my husband, and I coming to watch a horse show! Beautifully decorated, great shower!"
United States
Carrie D.
The price is HK$778
HK$1,697 total
includes taxes & fees
4 Jan - 5 Jan 2026
Springside Bourbon Getaway
Exterior
Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C

Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C

Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C
Lawrenceburg
10.0 out of 10, Exceptional, (4)
"Cute and comfortable place. I was very impressed and the host, Kyra was very communicative and great to work with! Will definitely be my "go-to" when I'm in the area again. "
United States
Lanita C.
The price is HK$567
HK$1,722 total
includes taxes & fees
1 Jan - 2 Jan 2026
Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Friendly staff! Great location "
Kim 2-night trip
Posted 3 days ago
Hyatt Regency Lexington

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?

Few and Proud: This holiday home rental outside of Midway is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 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 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 Lexington Ice Center, 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.