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Midway Vacation Rentals

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Our top choices for Midway vacation rentals

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 ¥40,498
¥73,495 total
includes taxes & fees
Dec 29 - Dec 30
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!

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 ¥22,104
¥37,172 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Bourbon Trail: Caboose on the Farm

Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland

Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
Lexington
10.0 out of 10, Exceptional, (286)
"Great visit "
United States
Titus M.
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland

Bourbon Trail Cabin on the Farm

Bourbon Trail Cabin on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (48)
"Fantastic location and great hosts!"
United States
James S.
The price is ¥14,736
¥27,766 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bourbon Trail Cabin on the Farm

Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky

Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky
Stamping Ground
9.8 out of 10, Exceptional, (6)
"Great hidden gem "
United States
lucian v.
The price is ¥18,385
¥32,474 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky

Five Minutes from Keeneland!

Five Minutes from Keeneland!
Versailles
10.0 out of 10, Exceptional, (23)
"The cottage was wonderful! Just what we needed and wanted. Jennifer is a great host and we will certainly stay again if the opportunity arises. "
United States
Matt T.
The price is ¥28,246
¥50,418 total
includes taxes & fees
Dec 28 - Dec 29
Five Minutes from Keeneland!

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 ¥11,368
¥34,538 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C

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 traveler
The price is ¥12,163
¥38,553 total
includes taxes & fees
Dec 29 - Dec 30
My Old Kentucky Home

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

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Georgetown
8.4 out of 10, Very Good, (32)
"We enjoyed our stay here very much. Thank you!"
United States
julianne k.
The price is ¥12,475
¥27,609 total
includes taxes & fees
Jan 3 - Jan 4, 2026
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Pet-Friendly Bluegrass Retreat w/ Fenced Yard
Georgetown
9.4 out of 10, Exceptional, (28)
"Cute quaint neighborhood, big back yard space, host very responsive. "
United States
Jenny M.
The price is ¥11,711
¥32,706 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Capital City Condo #8

Capital City Condo #8
Frankfort
8.6 out of 10, Excellent, (36)
"The condo was good for an overnight stay. The owners were very responsive & kind. Very close to just about anything you want to do. The price was good for the accommodations. Thank you for the hospitality! "
United States
Pollee F.
The price is ¥10,916
¥25,687 total
includes taxes & fees
Dec 27 - Dec 28
Capital City Condo #8

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 ¥10,916
¥25,687 total
includes taxes & fees
Dec 27 - Dec 28
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

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 ¥10,680
¥35,049 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy 1-bedroom in Lexington

Bourbon Trail Lakehouse - Pet Friendly!

Bourbon Trail Lakehouse - Pet Friendly!
Frankfort
9.8 out of 10, Exceptional, (50)
"Great place to stay!"
United States
Jeff S.
The price is ¥14,081
¥40,747 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Bourbon Trail Lakehouse - Pet Friendly!

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, (120)
"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 ¥19,955
¥32,669 total
includes taxes & fees
Dec 28 - Dec 29
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

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 ¥12,475
¥25,338 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Lexington Apt. with parking & private entrance Preview listing

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 ¥15,594
¥38,347 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Capital City Cottage

Bourbon Trail Getaway | Hot Tub • Fire Pit

Bourbon Trail Getaway | Hot Tub • Fire Pit
Lawrenceburg
10.0 out of 10, Exceptional, (22)
"Convenient location for the purpose of our stay."
United States
Scott S.
The price is ¥14,685
¥60,304 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bourbon Trail Getaway | Hot Tub • Fire Pit

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 ¥8,421
¥23,168 total
includes taxes & fees
Dec 28 - Dec 29
Treetops Solar Sanctuary

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (12)
"We stayed for our anniversary and visited some of the distilleries in the area. Our cabin was so cool and our stay was great. We would definitely book again"
United States
Evan C.
The price is ¥32,747
¥55,982 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bourbon Barrel Cottages #2 on Ky. 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.
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Top Midway Hotel Reviews

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:

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

Frequently asked questions

Can I find a vacation rental in Midway?

Yes, you can find vacation rentals near top points of interest in Midway, or you can choose a more secluded option if you'd like a relaxing place to 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's the top vacation rental in Midway?

Few and Proud: Visitors like this Midway vacation home rental. It is equipped with a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Midway?

With 9 Expedia vacation rentals, you're sure 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 vacation rental in Midway like?

Vacation rentals are private properties you can stay in for several days or longer in Midway. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.