A river winding through a lush green landscape with fields and trees.

Midway Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Midway holiday rentals

Dining

1. Family Fun Retreat - Pickleball, 9 Hole Mini Golf, Hot Tub + Fire Pit + Jukebox

Family Fun Retreat - Pickleball, 9 Hole Mini Golf, Hot Tub + Fire Pit + Jukebox
Midway
10.0 out of 10, Exceptional, (1 review)
"Great place for a family! Especially loved the jukebox and mini golf in the basement!"
United States
Austin P.
The price is HK$1,327
HK$2,664 total
includes taxes & fees
7 Sept - 8 Sept
Family Fun Retreat - Pickleball, 9 Hole Mini Golf, Hot Tub + Fire Pit + Jukebox
Interior

2. 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
9.6 out of 10, Exceptional, (7 reviews)
"The amenities were outstanding. The place was beautiful, clean, cozy and comfortable!"
United States
WILLIAM K.
The price is HK$2,036
HK$3,695 total
includes taxes & fees
8 Sept - 9 Sept
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!
Private kitchen

3. 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
9.4 out of 10, Exceptional, (97 reviews)
"Great property for our family. "
United States
Jake C.
The price is HK$1,184
HK$2,987 total
includes taxes & fees
8 Sept - 9 Sept
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Private kitchen

4. ⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!

⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!
Open Gates
10.0 out of 10, Exceptional, (85 reviews)
"Very grateful to stay here while we were at university of Kentucky healthcare with My Daughter! Great location"
United States
Callie W.
The price is HK$2,082
HK$4,218 total
includes taxes & fees
13 Sept - 14 Sept
⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!
Exterior

5. Bourbon Trail Lakehouse - Pet Friendly!

Bourbon Trail Lakehouse - Pet Friendly!
Frankfort
9.8 out of 10, Exceptional, (62 reviews)
"Great place to stay!"
United States
Jeff S.
The price is HK$856
HK$2,188 total
includes taxes & fees
6 Oct - 7 Oct
Bourbon Trail Lakehouse - Pet Friendly!
Interior

6. East Suite-🕊️ at Bleubird Studio, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (67 reviews)
"Always love staying at the Bluebird!"
United States
Julia A.
The price is HK$980
HK$1,824 total
includes taxes & fees
6 Sept - 7 Sept
East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Terrace/patio

7. Quiet-Country and Spacious Grandma's Duplex

Quiet-Country and Spacious Grandma's Duplex
Stamping Ground
9.6 out of 10, Exceptional, (58 reviews)
"We were in town for our granddaughters gradutation, so the location was perfect!"
United States
Sandy M.
The price is HK$862
HK$1,124 total
includes taxes & fees
8 Sept - 9 Sept
Quiet-Country and Spacious Grandma's Duplex
Room

8. 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, (33 reviews)
"Great house and yard!"
United States
Staci R.
The price is HK$884
HK$2,649 total
includes taxes & fees
7 Sept - 8 Sept
Hot Tub/Playground/12 min to Horse Park/30min Ark
Private kitchen

9. Game Room | King Suite | Firepit | Patio | Grill

Game Room | King Suite | Firepit | Patio | Grill
Georgetown
9.6 out of 10, Exceptional, (12 reviews)
"Very comfortable and beautiful! Enjoyed the lil fire pit area and that the back yard was fenced in for privacy. Excellent communication with host!!"
United States
Vicki S.
The price is HK$666
HK$2,316 total
includes taxes & fees
7 Sept - 8 Sept
Game Room | King Suite | Firepit | Patio | Grill
Outdoor spa tub

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

Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark
Georgetown
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful place. Well kept. Close to town. Kids' loft was a lot of fun. Host even provided guest robes and snacks. Would definitely stay again!"
United States
Julia B.
The price is HK$1,058
HK$2,745 total
includes taxes & fees
7 Sept - 8 Sept
Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark
Dining

11. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (348 reviews)
"Felt very comfortable during our stay,plenty of space for us both."
United States
Anonymous traveller
The price is HK$476
HK$523 total
includes taxes & fees
6 Sept - 7 Sept
2 Full Beds | Non-Smoking, Micfridge
Living area

12. Capital City Condo #2

Capital City Condo #2
Frankfort
9.2 out of 10, Wonderful, (71 reviews)
"Nice place, great host! Looking forward to coming back in October. Good location too"
United States
Country A.
The price is HK$549
HK$1,291 total
includes taxes & fees
6 Sept - 7 Sept
Capital City Condo #2
Living area

13. Capital City Condo #8

Capital City Condo #8
Frankfort
8.8 out of 10, Excellent, (41 reviews)
"This was our third time staying at this place for a bourbon trip. Overall it is a good value, has the basics and close to distilleries. "
United States
Robert V.
The price is HK$549
HK$1,291 total
includes taxes & fees
6 Sept - 7 Sept
Capital City Condo #8
Room

14. Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
Frankfort
8.8 out of 10, Excellent, (92 reviews)
"It was a nice stay"
United States
Teresa M.
The price is HK$549
HK$1,291 total
includes taxes & fees
16 Sept - 17 Sept
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
Private kitchen

15. 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, (43 reviews)
"A great stay! We enjoyed the hot tub after long days, and the living room was very comfortable. The house was easy to find, we walked to the Thai restaurant a block over nearly every night. We would stay again!"
United States
Araina R.
The price is HK$1,450
HK$3,267 total
includes taxes & fees
7 Sept - 8 Sept
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Interior

16. High style on the Bourbon Trail

High style on the Bourbon Trail
Versailles
10.0 out of 10, Exceptional, (119 reviews)
"This property was extremely clean, comfortable and in the perfect location to explore Horse and Bourbon Country. Our host, Albert, was close by in case we had any questions or problems. Would definitely rent this wonderful place again."
United States
Pamela C.
The price is HK$855
HK$1,556 total
includes taxes & fees
14 Sept - 15 Sept
High style on the Bourbon Trail
Exterior

17. Sleeps 8. Cozy Bungalow in Downtown Georgetown

Sleeps 8. Cozy Bungalow in Downtown Georgetown
Georgetown
9.8 out of 10, Exceptional, (21 reviews)
"We came in town for a UK graduation and the property was perfect for our needs. Comfortable beds and clean!"
United States
John S.
The price is HK$1,120
HK$2,662 total
includes taxes & fees
29 Sept - 30 Sept
Sleeps 8. Cozy Bungalow in Downtown Georgetown
Dining

18. Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown

Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
Georgetown
10.0 out of 10, Exceptional, (32 reviews)
"Great location for multiple bourbon trail experience."
United States
Mark S.
The price is HK$1,450
HK$3,267 total
includes taxes & fees
7 Sept - 8 Sept
Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
Interior

19. Capital City Condo #10

Capital City Condo #10
Frankfort
8.4 out of 10, Very good, (9 reviews)
"Such a great little place. Hosts are wonderful!"
United States
Amanda L.
The price is HK$549
HK$1,291 total
includes taxes & fees
12 Sept - 13 Sept
Capital City Condo #10
Living area

20. The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
10.0 out of 10, Exceptional, (30 reviews)
"Great property and wonderful hosts! "
United States
Jacinda C.
The price is HK$755
HK$1,857 total
includes taxes & fees
29 Sept - 30 Sept
The Bourbon Garage- walking distance to Buffalo Trace!
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

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

8/10 Good
"Perfect weekend, wonderful staff!"
Jamie 2-night trip
Posted 2 hours ago
Holiday Inn Express Lexington - Horse Park Area by IHG

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?

💙 BOURBON TRAIL on LAKE, HEATED POOL, GAME RM, PICKLEBALL, THEATRE, GOLF SIMULATOR!: This holiday home rental outside of Midway is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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 Masterson Station Park. In the wider area, you’ll find Equus Run Vineyard & Winery and The Kentucky Castle.

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.