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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Midway

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Relax on the deck surrounded by lush greenery and a vineyard backdrop.

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

10.0 out of 10, Exceptional, (273)
"Peaceful, relaxing, really enjoyed it"
The price is NZ$405
includes taxes & fees
18 Aug - 19 Aug
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Perfect Bourbon Trail Couple Getaway
Enjoy a peaceful stroll along the designated path, where a serene fire pit and bench invite relaxation.

Perfect Bourbon Trail Couple Getaway

10.0 out of 10, Exceptional, (25)
"Great property with a lot of warmth and charm."
Perfect Bourbon Trail Couple Getaway
Modern cottage located in the heart of the Bourbon Trail
Enjoy cooking in this well-equipped kitchen with an oven, stovetop, and range hood.

Modern cottage located in the heart of the Bourbon Trail

9.8 out of 10, Exceptional, (24)
"Very clean and great condition. Would stay again for sure. "
The price is NZ$372
includes taxes & fees
18 Aug - 19 Aug
Modern cottage located in the heart of the Bourbon Trail
Springside BoHo Getaway
Enter a cozy bedroom with a comfortable bed, bedside table, and chair.

Springside BoHo Getaway

10.0 out of 10, Exceptional, (46)
"We truly enjoyed our stay for our girls trip! The beds were SOOOOO comfortable and the house was clean and well stocked with everything we needed. It was convenient to walk to the local restaurants. Would stay again for sure! "
The price is NZ$528
includes taxes & fees
24 Aug - 25 Aug
Springside BoHo Getaway
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Cozy cabin-style building with a covered porch and large windows.

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

9.8 out of 10, Exceptional, (10)
"We had an amazing time at this beautiful cabin! Can not recommend enough! Thank you for an amazing trip!"
The price is NZ$449
includes taxes & fees
19 Aug - 20 Aug
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Cozy 1 bedroom cottage on picturesque horse farm
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and coffee station.

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (37)
"Everything about our stay was perfect! We had everything we needed in the cottage and it was very clean. Walking out & seeing the horses & sitting on the porch was very relaxing. "
Cozy 1 bedroom cottage on picturesque horse farm
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
3 bedrooms, iron/ironing board, WiFi, bed sheets

3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark

10.0 out of 10, Exceptional, (1)
"Amazing location, horses right outside the window. Perfect for the whole family"
The price is NZ$739
includes taxes & fees
11 Aug - 12 Aug
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Capital City Cottage
Cozy home with a gabled roof and a welcoming front porch.

Capital City Cottage

9.0 out of 10, Wonderful, (33)
"We were very pleased with he place. The beds were very comfortable and the amenities well thought out and nice."
The price is NZ$409
includes taxes & fees
15 Aug - 16 Aug
Capital City Cottage
Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky
Property grounds

Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky

9.6 out of 10, Exceptional, (4)
"Great hidden gem "
The price is NZ$351
includes taxes & fees
2 Sept - 3 Sept
Charming 1-bedroom cottage with WiFi and AC in lovely Stamping ky
Orchard Park cottage
Modern kitchen with central island, sink, and ample counter space, featuring stainless steel appliances and wooden cabinetry.

Orchard Park cottage

10.0 out of 10, Exceptional, (128)
"Property was in great condition with plenty of room for our family of 6. Loved visiting the horses and cows and the peacefulness of being in the country."
Orchard Park cottage
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Terrace/patio

Bourbon Barrel Cottages #5 on Ky. Bourbon Trail

10.0 out of 10, Exceptional, (11)
"Stayed here for my birthday weekend and it didn't disappoint. Perfect location and the cabin was beautiful. Definitely will be back! "
The price is NZ$723
includes taxes & fees
19 Aug - 20 Aug
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Spacious Frankfort Retreat on Bourbon Trail!
House (4 Bedrooms) | Interior

Spacious Frankfort Retreat on Bourbon Trail!

3.0 star property
Spacious Frankfort Retreat on Bourbon Trail!
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Compact kitchen with a central island, sink, and dining area.

Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.

10.0 out of 10, Exceptional, (33)
"The Farmhouse Cottage was perfect for our Derby weekend stay. The house is well-appointed with lots of special touches to make your stay more comfortable. It feels like staying in someone's home, not just any Vrbo. It has a rural feel, but is close to many attractions. Views from the porch are incredible, and a great place to drink a cup of coffee while watching the cows. Checking in and out were very easy, and the host was responsive."
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
Escape to a serene wooded retreat, where a gentle stream flows through a lush landscape.

Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.

9.8 out of 10, Exceptional, (16)
"We just loved staying in this home. It’s very nice and well decorated and has an amazing outside area "
Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
Cozy Cottage Perfect for Girls Night Away
Relax in a stylish living room with a sofa, armchairs, and a fireplace.

Cozy Cottage Perfect for Girls Night Away

10.0 out of 10, Exceptional, (9)
"We loved everything about our stay at the charming Lady Clay!! Can't recommend it enough!"
The price is NZ$1,023
includes taxes & fees
11 Aug - 12 Aug
Cozy Cottage Perfect for Girls Night Away
Five Minutes from Keeneland!
Staircase leads to an upper level, featuring turned balusters and a handrail.

Five Minutes from Keeneland!

10.0 out of 10, Exceptional, (21)
"We have stayed at many places in the area, as we visit family at least once a year—this was, by far, the best place we have stayed. The host had everything set up, including water in the refrigerator, coffee for Keurig, and a basket of breakfast goodies and snacks—all ready for our arrival. The host was very friendly and easygoing, and it was an absolute pleasure to stay there! 10/10 for sure!"
The price is NZ$578
includes taxes & fees
2 Sept - 3 Sept
Five Minutes from Keeneland!
Lovely Sadieville Retreat w/ Deck & Grill!
Kitchen area with dishwasher, dining table, and window offering a view of the outdoors.

Lovely Sadieville Retreat w/ Deck & Grill!

2.0 star property
10.0 out of 10, Exceptional, (2)
"We loved the peaceful location. Deer in the back yard in the evening. Horses from their farm in the side of the house in morning and evening. Close to The Ark Encounter. Clean and had what we needed. Great trip."
Lovely Sadieville Retreat w/ Deck & Grill!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Enjoy meals in this kitchen with a dining table and chairs, a chandelier, and a window.

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very clean."
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Bourbon Barrel Cabin A. There are 2 Cabins A & B.
Guests can enjoy a fire pit on the deck, surrounded by trees and gravel.

Bourbon Barrel Cabin A. There are 2 Cabins A & B.

10.0 out of 10, Exceptional, (2)
"This cabin was very nice and convenient to visit the Kentucky bourbon trail."
The price is NZ$449
includes taxes & fees
19 Aug - 20 Aug
Bourbon Barrel Cabin A. There are 2 Cabins A & B.
Two Bourbon Barrel Cabins
Enjoy a cozy evening by the fire pit on the balcony.

Two Bourbon Barrel Cabins

10.0 out of 10, Exceptional, (16)
"Great property in close proximity to the Bourbon Trail. Cabins were in excellent condition. Would definitely stay here again and highly recommend. "
The price is NZ$853
includes taxes & fees
19 Aug - 20 Aug
Two Bourbon Barrel Cabins
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
"Decor and condition was fantastic. We stopped overnight on our way back East, but after our experience, we are considering making a trip back just to stay in the Manchester again. Only drawbacks were limited seating in our room (stayed in the Quad) and both bars were closed by 11 pm on a Thursday night. "
heather 1-night trip
Posted 14 hours ago
The Manchester

Frequently asked questions

How much do cottages in Midway cost?
Expect to pay between NZ$351 and NZ$1,023 per night for cottages in Midway. Whatever your budget, an excellent stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Midway?
Use up your holiday days and pick from 53 cottages in Midway. Picturing a place where you can dive into nature and forget the world? Expedia will help you find your ideal stay in just a few clicks.
What is there to do in Midway near my cottage?
Once you've unpacked your things and settled in, head out and explore the fantastic things Midway has to offer. Equus Run Vineyard & Winery is a top attraction to add to your to-do list.