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Midway Holiday Rentals

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Holiday Rentals in Midway

Cozy cabin in the heart of horse country
10.0 out of 10, Exceptional, (29)
"The house was clean and conveniently located to Midway. It was stocked with everything we needed. The attached garage was an added bonus. Would stay again! "
Cozy cabin in the heart of horse country
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
9.6 out of 10, Exceptional, (236)
"The place was awesome and suited the bachelor party perfectly!"
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Location, Location, Location
9.2 out of 10, Wonderful, (62)
"Thank you for the use of your VRBO home. We had a wonderful stay, home is located minutes from downtown and Rupp arena. Lots of memories made, thank you again. "
The price is AU$332
includes taxes & fees
14 Oct - 15 Oct
Location, Location, Location
Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!
10.0 out of 10, Exceptional, (21)
"It's a wonderful house for a family visit, and its very convenient to Keeneland. "
The price is AU$1,456
includes taxes & fees
15 Oct - 16 Oct
Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
10.0 out of 10, Exceptional, (13)
"We had a remarkable time enjoying the entire property. Highly recommend! "
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Bourbon on Broadway
2.0 star property
10.0 out of 10, Exceptional, (15)
" wanted to visit. Just a nice place to stay big enough for taking Really enjoyed it. "
The price is AU$406
includes taxes & fees
4 Nov - 5 Nov
Bourbon on Broadway
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
2.0 star property
10.0 out of 10, Exceptional, (8)
"We absolutely loved our stay! The property was super nice and very spacious, it was in a perfect location to reach anywhere in downtown Lex. Will definitely book again!"
The price is AU$499
includes taxes & fees
26 Oct - 27 Oct
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
8.8 out of 10, Excellent, (35)
"Enjoyed our stay and location, would return in future "
The price is AU$300
includes taxes & fees
11 Nov - 12 Nov
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
10.0 out of 10, Exceptional, (115)
"Us and another couple came for a bourbon weekend. It was the perfect location between Bardstown and Frankfort. The location was a bit hard to find the first time especially at night, but the host gave great directions!"
The price is AU$349
includes taxes & fees
2 Nov - 3 Nov
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
10.0 out of 10, Exceptional, (92)
"Our family had a great time staying at this lodge! Everyone enjoyed all the activities that were available. The grand kids LOVED the pool, trampoline and playset. We all also enjoyed the firepit !! Great place to stay. Hope to stay here again in the near future!!"
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
Luxurious 1-bedroom with Free Parking
9.8 out of 10, Exceptional, (48)
"Extremely clean house with upgraded appliances. The kitchen was well stocked with everything you could need. Furnishings were comfortable. I would definitely stay here again! "
The price is AU$380
includes taxes & fees
22 Oct - 23 Oct
Luxurious 1-bedroom with Free Parking
Historic 1850 Towering Italianate Mansion
10.0 out of 10, Exceptional, (3)
"This house was perfect for us and our activity at the Kentucky Horse Park. Very close. Everything was clean, comfortable and easy. It's a great blend of historical with modern comfort. "
The price is AU$2,314
includes taxes & fees
14 Oct - 15 Oct
Historic 1850 Towering Italianate Mansion
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
8.4 out of 10, Very good, (37)
"Small but perfect for bourbon tour HQ"
The price is AU$271
includes taxes & fees
27 Oct - 28 Oct
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
9.8 out of 10, Exceptional, (146)
"Nice little home to stay in. Close to the places we wanted to visit. "
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
Lakefront Home Close to Bourbon Trail--Dog friendly!
9.8 out of 10, Exceptional, (79)
"Fantastic house and location! Close to the bourbon trail and cannot beat a morning coffee over looking the lake!"
Lakefront Home Close to Bourbon Trail--Dog friendly!
Charming 2-bedroom townhome with WiFi, AC in Lexington
2.0 out of 10, (1)
"Unfortunately my experience was less than favorable. The property was not as expected, and the response I received from the owner and from Vrbo was less than satisfactory. I would not recommend staying here until the owner finishes furnishing and cleans up inside and out. I would check to see if there are updated pictures on the site that show the front of the property, bathroom cabinet put together, clean inside and out, clean refrigerator, blinds down to ensure they are not broken and a secure...
Charming 2-bedroom townhome with WiFi, AC in Lexington
Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit
The price is AU$1,398
includes taxes & fees
11 Nov - 12 Nov
Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
10.0 out of 10, Exceptional, (5)
"Remote relaxation"
The price is AU$3,170
includes taxes & fees
15 Oct - 16 Oct
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
9.2 out of 10, Wonderful, (71)
"We so enjoyed this property. It was in a wonderful location...close to a park and convenient to shopping. Everything was just like it was described and pictured. We will definitely stay there again."
The price is AU$406
includes taxes & fees
29 Oct - 30 Oct
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
10.0 out of 10, Exceptional, (15)
"This house is very nice in a quiet neighborhood. Very clean with all the amenities. Communication with the host was excellent. Definitely would stay here again. "
The price is AU$641
includes taxes & fees
14 Oct - 15 Oct
The Luxe/Hot Tub/10 Min Keenland/12 Min Downtown/Fenced In Yard/ Pet Friendly
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

Everything you need to know about Midway holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Midway holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Midway holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Midway holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Midway holiday rentals we have selected for you start as low as AU$271 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Midway rentals

At Expedia, we put the best Midway holiday 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 holiday.

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 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 11 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.