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

Midway Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Midway vacation rentals

A dining room with a wooden table, black chairs, a chandelier, and floral wallpaper.

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 ￥26,626
￥50,504 total
includes taxes & fees
Sep 28 - Sep 29
Family Fun Retreat - Pickleball, 9 Hole Mini Golf, Hot Tub + Fire Pit + Jukebox
A modern kitchen with a marble countertop, stainless steel appliances, and a built-in oven.

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 ￥40,846
￥69,965 total
includes taxes & fees
Sep 29 - Sep 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!
A large, multi-story house with a central driveway and a pond in the background.

3. Bourbon Trail Lakehouse

Bourbon Trail Lakehouse
Frankfort
9.6 out of 10, Exceptional, (64 reviews)
"Great place to stay!"
United States
Jeff S.
The price is ￥17,836
￥44,273 total
includes taxes & fees
Sep 28 - Sep 29
Bourbon Trail Lakehouse
A woman in a blue floral dress opening a glass door to a patio with a dog, a potted plant, and a vase of flowers.

4. East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (71 reviews)
"Always love staying at the Bluebird!"
United States
Julia A.
The price is ￥19,660
￥35,544 total
includes taxes & fees
Sep 28 - Sep 29
East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to Downtown
A white house with a porch, stone wall, and a small garden.

5. 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, (304 reviews)
"Good size kitchen and master bedroom...big tv..comfy couch...nice dining table...quiet and private."
United States
Lindi
The price is ￥27,603
￥44,819 total
includes taxes & fees
Sep 28 - Sep 29
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
A brick exterior with a welcome mat, two white sofas, and a red chair.

6. Quiet-Country and Spacious Grandma's Duplex

Quiet-Country and Spacious Grandma's Duplex
Stamping Ground
9.6 out of 10, Exceptional, (59 reviews)
"We were in town for our granddaughters gradutation, so the location was perfect!"
United States
Sandy M.
The price is ￥17,301
￥22,540 total
includes taxes & fees
Sep 28 - Sep 29
Quiet-Country and Spacious Grandma's Duplex
A backyard with a stone fire pit, two metal chairs, and a wooden table.

7. 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
8.6 out of 10, Excellent, (36 reviews)
"Very nice comfortable and clean house. We had everything we needed while staying there. Nice area, plenty of space for the 4 of us. !"
United States
Esmeralda V.
The price is ￥12,582
￥27,846 total
includes taxes & fees
Sep 30 - Oct 1
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
A single-story house with a front porch, a garage, and a small front yard.

8. Sleeps 8. Cozy Bungalow in Downtown Georgetown

Sleeps 8. Cozy Bungalow in Downtown Georgetown
Georgetown
9.8 out of 10, Exceptional, (22 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 ￥17,340
￥45,787 total
includes taxes & fees
Sep 28 - Sep 29
Sleeps 8. Cozy Bungalow in Downtown Georgetown
A hot tub with a bottle and a glass of water on its edge.

9. 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)
"Great house the kids loved the upstairs and my teenage daughter loved the downstairs room. Great location for a family and a fun walk to main street downtown. "
United States
Timette W.
The price is ￥21,233
￥54,034 total
includes taxes & fees
Sep 29 - Sep 30
Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark
A bedroom with a bed, a ceiling fan, a large window, and a view of the outdoors.

10. 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.
Hot Tub/Playground/12 min to Horse Park/30min Ark
A modern kitchen with teal cabinets, a dining area with a wooden table and white chairs, and a cozy seating area with a patterned rug and a potted plant.

11. High style on the Bourbon Trail

High style on the Bourbon Trail
Versailles
10.0 out of 10, Exceptional, (122 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 ￥17,144
￥31,037 total
includes taxes & fees
Sep 29 - Sep 30
High style on the Bourbon Trail
A modern living room with a sofa, a coffee table, and a bed.

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

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
10.0 out of 10, Exceptional, (33 reviews)
"Great property and wonderful hosts! "
United States
Jacinda C.
The price is ￥14,863
￥36,918 total
includes taxes & fees
Sep 28 - Sep 29
The Bourbon Garage- walking distance to Buffalo Trace!
A modern kitchen with a wooden bar counter, two stools, a television, and a window with blinds.

13. 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.
Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
A modern kitchen with stainless steel appliances, a built-in oven, and a refrigerator. There is a living area with a sofa, coffee table, and a flat-screen TV.

14. 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, (46 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 ￥29,097
￥61,898 total
includes taxes & fees
Sep 28 - Sep 29
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
A living room with a sofa, a coffee table, a rug, and a bookshelf.

15. 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, (110 reviews)
"Perfect location for the Bourbon Trail. Nice, clean, and affordable. 10 out of 10, would do it again!"
United States
Dwight K.
The price is ￥11,010
￥25,908 total
includes taxes & fees
Sep 30 - Oct 1
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
A reception area with a mounted TV displaying various streaming services, a wooden console with a welcome sign, and a seating area with a table and chairs.

16. Capital City Condo #10

Capital City Condo #10
Frankfort
8.2 out of 10, Very good, (10 reviews)
"Such a great little place. Hosts are wonderful!"
United States
Amanda L.
The price is ￥11,010
￥25,908 total
includes taxes & fees
Sep 28 - Sep 29
Capital City Condo #10
A hotel lobby with a flat-screen TV, a coat rack, a table with chairs, and a view of the outside through large glass doors.

17. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (348 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveler
The price is ￥9,671
￥10,638 total
includes taxes & fees
Oct 4 - Oct 5
2 Full Beds | Non-Smoking, Micfridge
A neatly arranged bedroom with a large bed, two bedside lamps, a wooden floor, a wall-mounted painting, and a sliding door.

18. "The Meridian" Modern Stay near Downtown / Airport with Hot Tub

"The Meridian" Modern Stay near Downtown / Airport with Hot Tub
Lexington
9.8 out of 10, Exceptional, (41 reviews)
"This was an amazing stay! Everything was exactly as described and the communication with hosts was the best I’ve ever had! Would highly recommend this place if you are ever in the area. Thank you for an incredibly wonderful experience!"
United States
Brian R.
"The Meridian" Modern Stay near Downtown / Airport with Hot Tub
A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

19. 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 ￥11,010
￥25,908 total
includes taxes & fees
Sep 28 - Sep 29
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
A beige sofa with patterned cushions, a dark patterned rug, and a window with blinds.

20. Capital City Condo #8

Capital City Condo #8
Frankfort
8.8 out of 10, Excellent, (42 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 ￥11,010
￥25,908 total
includes taxes & fees
Sep 28 - Sep 29
Capital City Condo #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

Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

8/10 Good
"Place was clean and comfortable."
Dennis 1-night trip
Posted 1 hour ago
Microtel Inn by Wyndham 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
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  • 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 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?

💙 BOURBON TRAIL on LAKE, HEATED POOL, GAME RM, PICKLEBALL, THEATRE, GOLF SIMULATOR!: Visitors like this Midway vacation home rental. It is located on a lake and has a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Midway?

With 11 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 Blue Grass Railroad Museum, or get outside and enjoy nature at Masterson Station Park. In the larger area, you’ll find Equus Run Vineyard & Winery and The Kentucky Castle.

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.