Vacation rentals in Midway

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Top-rated vacation rentals in Midway

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Guest favourite

Apartment in Versailles

4.99 out of 5 average rating, 266 reviews

High style on the Bourbon Trail

Historic 1 bedroom apt in the heart of horse country & the bourbon trail. Central Main St. location in charming Versailles, steps away from local coffee shop and bourbon bar. Walk to restaurants, shopping and park. Light filled apartment with vaulted ceiling and exposed brick wall. Cozy bedroom has memory foam Cal king bed and percale cotton sheets. The decor is an eclectic mix of antiques, Ferrick Mason textiles, wallpapers and Alex K Mason original art. Parking space. Free washer & dryer.

Dec. 9 – 16

$194 CAD per night

Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 260 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Sep. 2 – 9

$248 CAD per night

Guest favourite

Home in Stamping Ground

4.97 out of 5 average rating, 604 reviews

Buffalo Springs Distilling Company

On the Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one bedroom due to the size of the structure. Queen size bed in the bedroom. There’s also a Queen Air Mattress that can be utilized in a pinch for folks that are staying at least a week

Mar. 3 – 10

$238 CAD per night

Guest favourite

Farm stay in Versailles

4.91 out of 5 average rating, 393 reviews

Bluegrass Country Cottage

Enjoy a quaint, private, quiet & charming little place to call your own, on a small, working (seasonal) Thoroughbred horse farm. Green acreage, lovely scenes and sunsets. Located in horse country, between historic Winstar Farm and Lane's End Farm, just a short drive to small town USA, Versailles; historic Midway; and to the nearby City of Lexington, home of the Kentucky Wildcats, Horse Capital of the World, Bourbon Country & so much more. Pets allowed (2 max), well behaved, pet fee applies.

Jul. 1 – 8

$260 CAD per night

Guest favourite

Guesthouse in Nicholasville

4.98 out of 5 average rating, 297 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Jun. 15 – 22

$140 CAD per night

Guest favourite

Guesthouse in Lexington

4.91 out of 5 average rating, 162 reviews

Horse Farm Cottage near Keeneland and Horse Park

PROFESSIONALLY SANITIZED EVERY VISIT! This updated and professionally decorated cottage is located on a beautiful 120 acre horse farm 5 minutes from the Horse Park, 10 minutes from Keeneland and the airport, and 20 minutes from downtown Lexington. There are many activities located close by such as: horse races, horse competitions, Woodford Reserve, Buffalo Trace, and so much more! In addition, the farm can also be rented out as a wedding and events venue. https://www.antebellumfarm.net/home

Sep. 21 – 28

$242 CAD per night

Guest favourite

Cabin in Sadieville

4.97 out of 5 average rating, 247 reviews

*Unique Country Cabin *1BR 20 min from The Ark!

No neighbors! It’s not a big or fancy place but it’s clean, simple, and relaxing. The stars are brightest in the country when enjoying the fire pit. Our two story cabin has 1BR with two double beds, full kitchen, full bathroom, recliners, and grills. It's perfect for couples, friends, or small families. The Ark Encounter, Kentucky Horse Park, Keeneland, and several distilleries are all within an hour of the cabin. This is a great place to relax between visits to these attractions.

Jul. 29 – Aug. 5

$153 CAD per night

Guest favourite

Treehouse in Georgetown

4.94 out of 5 average rating, 167 reviews

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

May 12 – 19

$270 CAD per night

Guest favourite

Farm stay in Midway

5.0 out of 5 average rating, 6 reviews

Peaceful Country Setting

If you're looking for a peaceful place to rest while visiting the Kentucky Horse Park or traveling the Bourbon Trail this 1 bedroom apartment is what you're looking for. Situated on the second floor of a charming farmhouse, this apartment boasts beautiful views of the surrounding horse properties. You're also not far from Midway University, Georgetown College, UK, Kentucky State, and Transylvania University. The apartment has a full kitchen, dining area, living room and shared laundry.

Sep. 22 – 29

$162 CAD per night

Guest favourite

Apartment in Midway

4.89 out of 5 average rating, 92 reviews

Downtown Midway Loft--Walk Everywhere!

Located 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!

May 16 – 23

$197 CAD per night

Guest favourite

Tiny homes in Frankfort

4.98 out of 5 average rating, 331 reviews

Tiny Home with Huge Charm near the Elkhorn Creek

Just minutes from downtown Frankfort, this place is a little peaceful country getaway with a lot to offer! It’s nestled on a quiet street with great access to the beautiful Elkhorn Creek! If you’re into Bourbon tours, Horses, canoeing/kayaking/fishing, or Natural and Historical sites, this place is a great location in the middle of a lot to see and do! The tiny house has a small kitchen and bath as well as a yard and private patio and grill to enjoy!

Aug. 17 – 24

$158 CAD per night

Guest favourite

Farm stay in Georgetown

4.98 out of 5 average rating, 321 reviews

Have a great stay at Great Crossings Farm!

Our solar farm lies in the heart of the bluegrass! We live near: Old Friends Farm, the KY Horse Park, and 35 minutes from UK, Keeneland, The Ark, and 5 distilleries. We live on a small 6 acre farm with cows, sheep, goats, & chickens. Drop by the barn and meet & feed the sheep and goats! You also can watch a movie with them with the little "theater" in the barn. Our house is pretty much a duplex--two houses under one roof, both separate.

Jul. 24 – 31

$205 CAD per night