Midway Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Midway holiday rentals

Interior

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!
Midway
10.0 out of 10, Exceptional, (2 reviews)
"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$2,029
HK$3,682 total
includes taxes & fees
11 Feb - 12 Feb
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!
Interior

Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (38 reviews)
"Loved every aspect of this unique stay! From the very cool caboose to friendly farm animals, we hope to be back again!"
United States
Cindi M.
The price is HK$1,108
HK$1,837 total
includes taxes & fees
16 Feb - 17 Feb
Bourbon Trail: Caboose on the Farm
Interior

Five Minutes from Keeneland!

Five Minutes from Keeneland!
Versailles
10.0 out of 10, Exceptional, (23 reviews)
"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 HK$1,414
HK$2,506 total
includes taxes & fees
12 Feb - 13 Feb
Five Minutes from Keeneland!
Exterior

2 Bed/2 Bath/Game Room

2 Bed/2 Bath/Game Room
Lawrenceburg
10.0 out of 10, Exceptional, (122 reviews)
"Great central location for our stay! Than you so much. Would absolutely recommend this to everyone!"
United States
Patrick
The price is HK$1,016
HK$1,637 total
includes taxes & fees
11 Feb - 12 Feb
2 Bed/2 Bath/Game Room
Property grounds

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Frankfort
9.8 out of 10, Exceptional, (15 reviews)
"Property was clean and comfy! Would stay again. "
United States
Amy L.
The price is HK$1,094
HK$1,915 total
includes taxes & fees
12 Feb - 13 Feb
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Interior

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 reviews)
"Very cozy! The owners are incredibly kind and available if you need anything. Their hospitality is top notch, and we will definitely be back! "
United States
Whitney M.
The price is HK$1,024
HK$1,732 total
includes taxes & fees
10 Mar - 11 Mar
Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky
Property grounds

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (12 reviews)
"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 HK$1,641
HK$2,728 total
includes taxes & fees
11 Mar - 12 Mar
Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Property grounds

Bourbon Trail Cabin on the Farm

Bourbon Trail Cabin on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (49 reviews)
"Awesome place. Just stayed overnight but will be back just to relax in the cabin. The surroundings are so peaceful and the animals were fun. "
United States
Rachel P.
The price is HK$739
HK$1,392 total
includes taxes & fees
22 Feb - 23 Feb
Bourbon Trail Cabin on the Farm
Interior

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Georgetown
10.0 out of 10, Exceptional, (60 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
The price is HK$977
HK$1,766 total
includes taxes & fees
1 Mar - 2 Mar
East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Terrace/patio

Bourbon Trail Getaway | Hot Tub • Fire Pit

Bourbon Trail Getaway | Hot Tub • Fire Pit
Lawrenceburg
10.0 out of 10, Exceptional, (25 reviews)
"Convenient location for the purpose of our stay."
United States
Scott S.
The price is HK$774
HK$3,181 total
includes taxes & fees
26 Feb - 27 Feb
Bourbon Trail Getaway | Hot Tub • Fire Pit
Outdoor dining

Original Circa 1818 Oak Lodge

Original Circa 1818 Oak Lodge
Lawrenceburg
9.4 out of 10, Exceptional, (53 reviews)
"Great communication. Very clean property."
United States
Alan D.
The price is HK$1,172
HK$2,162 total
includes taxes & fees
2 Mar - 3 Mar
Original Circa 1818 Oak Lodge
Terrace/patio

Scenic Highgrounds Modern Cabin - Chicory

Scenic Highgrounds Modern Cabin - Chicory
Frankfort
9.6 out of 10, Exceptional, (4 reviews)
"The cabin is located on a huge beautiful farm. When it wasnt raining we enjoyed hiking the trails and checking out the wild life.will definitely consider staying again!"
United States
Crystal S.
The price is HK$1,042
HK$2,226 total
includes taxes & fees
11 Feb - 12 Feb
Scenic Highgrounds Modern Cabin - Chicory
Outdoor spa tub

Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark

Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark
Georgetown
9.6 out of 10, Exceptional, (25 reviews)
"Worked out perfect for a game day weekend."
United States
Colby H.
The price is HK$950
HK$2,641 total
includes taxes & fees
11 Feb - 12 Feb
Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark
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.
Frankfort
10.0 out of 10, Exceptional, (33 reviews)
"very clean, bedrooms spacious, horses and other animals made for very nice stay."
United States
Richard N.
The price is HK$1,118
HK$2,297 total
includes taxes & fees
19 Feb - 20 Feb
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Dining

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
Lexington
10.0 out of 10, Exceptional, (9 reviews)
"Nice and quiet street. Easy check in. Host was very responsive and made sure we were taken care of. "
United States
Michael D.
The price is HK$953
HK$2,531 total
includes taxes & fees
11 Feb - 12 Feb
Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's
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, (33 reviews)
"It was very nice and clean and very comfortable! "
United States
Denise N.
The price is HK$1,446
HK$3,016 total
includes taxes & fees
11 Mar - 12 Mar
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Exterior

Bourbon Trail Lakehouse - Pet Friendly!

Bourbon Trail Lakehouse - Pet Friendly!
Frankfort
9.8 out of 10, Exceptional, (51 reviews)
"Great place to stay!"
United States
Jeff S.
The price is HK$657
HK$1,969 total
includes taxes & fees
11 Feb - 12 Feb
Bourbon Trail Lakehouse - Pet Friendly!
Exterior

# 1 on Ky. Bourbon Trail HOT TUB all distilleries

# 1 on Ky. Bourbon Trail HOT TUB all distilleries
Lawrenceburg
10.0 out of 10, Exceptional, (26 reviews)
"Great, secluded location far enough away for peace and quiet yet close enough to lots of fun activities."
United States
Kevin B.
The price is HK$1,641
HK$2,789 total
includes taxes & fees
11 Feb - 12 Feb
# 1 on Ky. Bourbon Trail HOT TUB all distilleries
Smart TV

My Old Kentucky Home

My Old Kentucky Home
Lexington
10.0 out of 10, Exceptional, (27 reviews)
"Great place for a nice weekend visit."
United States
brian g.
My Old Kentucky Home
Fridge, microwave, oven, stovetop

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
10.0 out of 10, Exceptional, (19 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is HK$1,140
HK$3,455 total
includes taxes & fees
11 Feb - 12 Feb
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
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
"Friendly and attentive staff. Great location, bar and onsite restaurant. "
Donna 1-night trip
Posted 23 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?

Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28: This holiday home rental outside of Midway is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.