Vacation rentals in Midway

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Top-rated vacation rentals in Midway

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Guest favorite

Apartment in Versailles

4.99 out of 5 average rating, 265 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

$106 per night

Guest favorite

Home in Stamping Ground

4.97 out of 5 average rating, 603 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

Oct 2 – 9

$138 per night

Guest favorite

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!

Mar 21 – 28

$135 per night

Guest favorite

Home in Georgetown

4.98 out of 5 average rating, 128 reviews

Hot Tub Hide-A-Way | Horse Park 11min/Ark 30min

Entire Luxury Home Hide-A-Way In Down Town Georgetown, KY. Featuring An Inflatable Hot Tub, Purple Mattress (Queen), Additional Pull Out Couch Bed, 65in 4K TV. *Please No Shoes* Security System/Cameras (Door Bell & Back Yard) 5 min Walk To Local Restaurants/Bars - Local Feed, Galvins etc 12 Min KY Horse Park 30 Min Ark Encounter 🚨 Ask about our 3 bedroom home “The Retro” directly behind this listing for traveling friends / family who would like to book close but stay in separate homes. 🚨

May 8 – 15

$122 per night

Guest favorite

Farm stay in Georgetown

4.95 out of 5 average rating, 217 reviews

Horse Country Heaven

Come check out Dunn Driftin guest cabin in the heart of horse country and have your very own cozy hideout while experiencing all that central Kentucky has to offer. Take a tour of the top-notch thoroughbred farms, go on the Bourbon Trail adventure, explore the Ky horse park, catch a race at Keeneland (April & October), or venture out to Churchill downs or the Ark Encounter. Oh, and just so you know, we love dogs! Additionally, we provide horse boarding and even massage therapy for an extra fee.

Oct 23 – 30

$167 per night

Guest favorite

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.

Jun 29 – Jul 6

$140 per night

Guest favorite

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 18 – 25

$85 per night

Guest favorite

Guesthouse in Lexington

4.91 out of 5 average rating, 161 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 27 – Oct 4

$125 per night

Guest favorite

Treehouse in Georgetown

4.94 out of 5 average rating, 166 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

$154 per night

Guest favorite

Home in Versailles

4.93 out of 5 average rating, 120 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Mar 19 – 26

$115 per night

Guest favorite

Cabin in Versailles

4.97 out of 5 average rating, 120 reviews

Handcrafted Rustic Cabin on the Bourbon Trail

The cabin has been entirely built by the owner, Doris, (with help from family and friends) from reclaimed and local salvaged materials. Located on a beautiful Kentucky Scenic byway, on a working farm, the cabin is only 15 minutes from Wild Turkey Distillery, the town of Versailles , golf courses, dining, shopping, wineries and other major distilleries. 35 minutes from Keeneland race course, downtown Lexington, UK, Rupp Arena, the Horse Park and more .

Jan 9 – 16

$127 per night

Guest favorite

Tiny home 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!

Jul 25 – Aug 1

$91 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Midway vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Apartment in Midway

4.97 out of 5 average rating, 73 reviews

Modern Remodeled Downtown Midway Studio

Jul 26 – Aug 2

$101 per night

Guest favorite

Apartment in Midway

4.89 out of 5 average rating, 92 reviews

Downtown Midway Loft--Walk Everywhere!

May 16 – 23

$115 per night

Guest favorite

Farm stay in Midway

5.0 out of 5 average rating, 6 reviews

Peaceful Country Setting

Jan 6 – 13

$76 per night

Guest favorite

Home in Midway

4.99 out of 5 average rating, 96 reviews

Country Cottage in Horse and Bourbon Country

Jul 3 – 10

$144 per night

Guest favorite

Home in Midway

5.0 out of 5 average rating, 62 reviews

Midway Cottage, Keeneland, Distilleries, Pool

Aug 11 – 18

$295 per night

Guest favorite

Farm stay in Midway

5.0 out of 5 average rating, 87 reviews

Saxony Farm - The Dew Drop In

Dec 21 – 28

$443 per night

Guest favorite

Home in Midway

5.0 out of 5 average rating, 54 reviews

Midway Cottage-Vineyard, Bourbon Trail, Horses

Mar 7 – 14

$225 per night

Guest favorite

Home in Midway

4.99 out of 5 average rating, 67 reviews

The Bees Wing

Mar 11 – 18

$376 per night

Show all

Quick stats about vacation rentals in Midway

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
840 reviews
Nightly prices starting at
$40 before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Midway?
Midway has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
Are there vacation rentals with a dedicated workspace in Midway?
Yes! Work meets play with ease at over 10 vacation rentals in Midway featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Midway

Top-rated vacation rentals in Midway

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Midway vacation rentals

Stay near Midway's top sights

Other great vacation rentals in Midway

Apartment in Midway

Apartment in Midway

Farm stay in Midway

Home in Midway

Home in Midway

Farm stay in Midway

Home in Midway

Home in Midway

Quick stats about vacation rentals in Midway

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Midway?

Do house rentals in Midway have air conditioning?

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

Do house rentals in Midway have wifi?

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

Are there vacation rentals with a dedicated workspace in Midway?

Destinations to explore