Vacation rentals in Midway

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Top-rated vacation rentals in Midway

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

Guest favorite

Home in Stamping Ground

4.97 out of 5 average rating, 596 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

Feb 26 – Mar 5

G$33,048 GYD per night
Guest favorite

Apartment in Versailles

4.99 out of 5 average rating, 260 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.

Aug 20 – 27

G$25,656 GYD per night
Guest favorite

Train in Lawrenceburg

4.98 out of 5 average rating, 250 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!

Aug 30 – Sep 6

G$31,868 GYD per night

Popular amenities for Midway vacation rentals

Stay near Midway's top sights

The Brown Barrel & Blind Harry's12 locals recommend
The Goose & Gander11 locals recommend
Mezzo Italian Cafe and Provisions7 locals recommend
Darlin Jean's Apple Cobbler Cafe9 locals recommend
Heirloom Restaurant30 locals recommend
Holly Hill Inn26 locals recommend

Other great vacation rentals in Midway

Guest favorite

Farm stay in Georgetown

4.95 out of 5 average rating, 211 reviews

Horse Country Heaven

Dec 28 – Jan 4

G$40,270 GYD per night
Guest favorite

Apartment in Midway

4.97 out of 5 average rating, 72 reviews

Modern Remodeled Downtown Midway Studio

Aug 28 – Sep 4

G$24,186 GYD per night
Guest favorite

Apartment in Midway

4.89 out of 5 average rating, 90 reviews

Downtown Midway Loft--Walk Everywhere!

May 15 – 22

G$29,184 GYD per night
Guest favorite

Home in Midway

4.99 out of 5 average rating, 94 reviews

Country Cottage in Horse and Bourbon Country

Jul 24 – 31

G$29,369 GYD per night
Guest favorite

Farm stay in Midway

5.0 out of 5 average rating, 5 reviews

Peaceful Country Setting

Dec 22 – 29

G$19,124 GYD per night
Guest favorite

Home in Midway

5.0 out of 5 average rating, 61 reviews

Midway Cottage, Keeneland, Distilleries, Pool

Sep 5 – 12

G$70,827 GYD per night
Guest favorite

Home in Midway

4.99 out of 5 average rating, 67 reviews

The Bees Wing

Dec 29 – Jan 5

G$91,029 GYD per night
Guest favorite

Home in Midway

5.0 out of 5 average rating, 53 reviews

Midway Cottage-Vineyard, Bourbon Trail, Horses

Dec 11 – 18

G$54,095 GYD per night
Guest favorite

Cabin in Midway

4.96 out of 5 average rating, 24 reviews

Kentucky breeze cabin

Jan 22 – 29

G$60,255 GYD per night
Guest favorite

Farm stay in Stamping Ground

5.0 out of 5 average rating, 64 reviews

Step into our World of Horses. Share our Dream!

Jun 19 – 26

G$29,586 GYD per night
Guest favorite

Loft in Georgetown

4.98 out of 5 average rating, 47 reviews

New! Loft above Horse Barn on Bourbon Trail!

Oct 30 – Nov 6

G$65,370 GYD per night
Guest favorite

Home in Georgetown

4.94 out of 5 average rating, 36 reviews

Horse Country Getaway in Charming Georgetown

Nov 30 – Dec 7

G$27,084 GYD per night

Quick stats about vacation rentals in Midway

Total rentals

10 properties

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

10 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

820 reviews

Nightly prices starting at

G$8,378 GYD before taxes and fees

Frequently Asked Questions

  • Do house rentals in Midway have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Midway. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Midway?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Midway have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Midway. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Midway?

    Experience the best of Midway with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Woodford County
  5. Midway