Skip to content

Vacation rentals in Midway

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Midway

Guests agree: these stays are highly rated for location, cleanliness, and more.

New! Downtown Midway Loft
Entire rental unit · 2 guests · 1 bed · 1 bath
New! Downtown Midway LoftLocated in the heart of downtown Midway, this renovated studio apartment in an 1890's Whiskey Warehouse makes for the perfect retreat. The bedroom features a queen sized Tempur-Pedic mattress, ROKU TV, and desk. Plan your day with a morning coffee in the full kitchen that's equipped with basic cookware for prepping light meals. The apartment is located on the third floor, so pack light as it is accessed only by stairs. We delight to host your stay in beautiful Kentucky!
A Little Peace in Midway KY
SUPERHOST
Private room · 2 guests · 1 bed · 1.5 baths
A Little Peace in Midway KYMy home is a peaceful corner of Midway with a surprising view out back
The Ainsley  Suite
SUPERHOST
Entire rental unit · 3 guests · 2 beds · 1 bath
The Ainsley SuiteHistoric upstairs apartment in Midway Kentucky, Located downtown just steps from dining, bakery and local shopping. Midway is in the middle of the Bourbon Trail, easy drive to the Kentucky Horse Park as well as Keenland Racetrack. Multiple Vineyards are also close by.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Midway

SUPERHOST
  1. Farm stay
  2. Midway
Wintergreen Cottage
$105 per night
SUPERHOST
  1. Private room
  2. Midway
Bluegrass Country, aPerfect Room for you in Midway
$48 per night
SUPERHOST
  1. Entire residential home
  2. Midway
Bit and Bourbon
$235 per night
SUPERHOST
  1. Entire rental unit
  2. Midway
Trackside Suite
$150 per night
SUPERHOST
  1. Entire residential home
  2. Midway
Minutes to Keeneland Restored 1901 Midway Cottage
$235 per night
  1. Entire residential home
  2. Midway
HORSE COUNTRY COTTAGE
$225 per night
SUPERHOST
  1. Entire residential home
  2. Midway
The Bees Wing
$400 per night
  1. Entire residential home
  2. Midway
Saddlestone Cottage-Bourbon, Horses, Outdoors
$225 per night
SUPERHOST
  1. Entire residential home
  2. Midway
HOLIDAY HOUSE - Bluegrass Horse Farm Estate
$1,545 per night
SUPERHOST
  1. Entire rental unit
  2. Midway
Bluegrass Suite
$150 per night
SUPERHOST
  1. Private room
  2. Midway
Welcome to Midway
$60 per night
  1. Entire residential home
  2. Midway
Crow's Nest- Exclusive Spot in Downtown Midway
$65 per night