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 modern kitchen with a marble countertop, stainless steel appliances, and a built-in oven.

1. 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 CA $364
CA $661 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 dining room with a wooden table, black chairs, a chandelier, and floral wallpaper.

2. 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 CA $238
CA $477 total
includes taxes & fees
Sep 28 - Sep 29
Family Fun Retreat - Pickleball, 9 Hole Mini Golf, Hot Tub + Fire Pit + Jukebox
A white house with a porch, stone wall, and a small garden.

3. 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 CA $210
CA $369 total
includes taxes & fees
Sep 28 - Sep 29
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
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, (70 reviews)
"Always love staying at the Bluebird!"
United States
Julia A.
The price is CA $175
CA $325 total
includes taxes & fees
Sep 28 - Sep 29
East Suite-🕊️ at Bleubird Studio, Luxury stay, Walk to 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.

5. 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, (45 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 CA $260
CA $593 total
includes taxes & fees
Sep 28 - Sep 29
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
A modern kitchen with a wooden bar counter, two stools, a television, and a window with blinds.

6. 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 CA $260
CA $593 total
includes taxes & fees
Sep 28 - Sep 29
Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
A covered outdoor seating area with a view of a river and trees.

7. Modern creekside cabin on 32 private acres. 15 minutes from Buffalo Trace!

Modern creekside cabin on 32 private acres. 15 minutes from Buffalo Trace!
Frankfort
10.0 out of 10, Exceptional, (11 reviews)
"We had a fantastic stay. Highly recommend everyone to stay at this house. The house was very clean and had beautiful views. The Host was responsive and was very polite."
United States
Brendan H.
The price is CA $491
CA $955 total
includes taxes & fees
Sep 29 - Sep 30
Modern creekside cabin on 32 private acres. 15 minutes from Buffalo Trace!
A brick exterior with a welcome mat, two white sofas, and a red chair.

8. 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 CA $154
CA $201 total
includes taxes & fees
Sep 28 - Sep 29
Quiet-Country and Spacious Grandma's Duplex
A large, multi-story house with a central driveway and a pond in the background.

9. 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 CA $144
CA $398 total
includes taxes & fees
Sep 29 - Sep 30
Bourbon Trail Lakehouse
A single-story house with a porch, a small garden, and a visible window.

10. Greenwood Farm log cabin close to the Bourbon Trail and Keeneland

Greenwood Farm log cabin close to the Bourbon Trail and Keeneland
Versailles
10.0 out of 10, Exceptional, (34 reviews)
"My co workers and I had a great stay."
United States
accounting
The price is CA $344
CA $614 total
includes taxes & fees
Oct 6 - Oct 7
Greenwood Farm log cabin close to the Bourbon Trail and Keeneland
A bedroom with a bed, a ceiling fan, a large window, and a view of the outdoors.

11. 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 CA $176
CA $503 total
includes taxes & fees
Sep 28 - Sep 29
Hot Tub/Playground/12 min to Horse Park/30min Ark
A covered outdoor area with a wooden deck, a bench, and a fire hydrant.

12. Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!

Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!
Frankfort
10.0 out of 10, Exceptional, (37 reviews)
"Lovely home with lots of amenities. Loved watching the deer and hearing all the birds really made our visit enjoyable."
United States
Linda C.
The price is CA $253
CA $465 total
includes taxes & fees
Sep 28 - Sep 29
Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!
A hot tub with a bottle and a glass of water on its edge.

13. 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 CA $189
CA $519 total
includes taxes & fees
Sep 29 - Sep 30
Hot Tub & Fireplace/12min to Horse Park/30 Min to Ark
A modern kitchen with white cabinets, a black refrigerator, granite countertops, and pendant lighting.

14. 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 CA $122
CA $424 total
includes taxes & fees
Sep 28 - Sep 29
Game Room | King Suite | Firepit | Patio | Grill
A single-story house with a front porch, a garage, and a small front yard.

15. 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 CA $155
CA $435 total
includes taxes & fees
Sep 28 - Sep 29
Sleeps 8. Cozy Bungalow in Downtown Georgetown
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.

16. 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 traveller
The price is CA $87
CA $96 total
includes taxes & fees
Oct 6 - Oct 7
2 Full Beds | Non-Smoking, Micfridge
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.

17. High style on the Bourbon Trail

High style on the Bourbon Trail
Versailles
10.0 out of 10, Exceptional, (121 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 CA $153
CA $280 total
includes taxes & fees
Sep 29 - Sep 30
High style on the Bourbon Trail
A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

18. 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 CA $98
CA $231 total
includes taxes & fees
Sep 24 - Sep 25
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
A neatly arranged bedroom with a large bed, two bedside lamps, a wooden floor, a wall-mounted painting, and a sliding door.

19. "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 price is CA $157
CA $439 total
includes taxes & fees
Sep 27 - Sep 28
"The Meridian" Modern Stay near Downtown / Airport with Hot Tub
A living room with a sofa, a coffee table, a rug, and a bookshelf.

20. 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 CA $98
CA $231 total
includes taxes & fees
Sep 24 - Sep 25
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
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

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

10/10 Excellent
"Loved it here!"
Leslie 2-night trip
Posted 3 hours ago
Origin Lexington a Wyndham Hotel

Find out more about Midway

Everything you need to know about Midway vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Midway vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Midway vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Midway vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Midway. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Midway vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Midway vacation rentals we have selected for you start as low as CA $96 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Midway rentals

At Expedia, we put the best Midway vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Midway rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Midway vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Midway. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.