Vacation rentals in Middleburg

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Popular amenities for Middleburg vacation rentals

Other great vacation rentals in Middleburg

Top guest favorite
A covered patio is illuminated by string lights, offering a cozy space with a round table and four chairs. A patterned rug enhances the area, while a grassy backyard is visible through the railing. A shed can be seen in the background.
Home in Bardstown
4.97 out of 5 average rating, 33 reviews

*Sweet Southern Comfort* 3 Qn bd 2+bth sleeps 6

CarolynRating, 5 stars4 weeks ago
The house was perfect for our needs! We were partaking of the bourbon trail and were also able to work a thoroughbred tour at Winstar farms in as well - would highly recommend. The decor and floor plan is very comfortable and inviting. The porch out back was very nice for a nosh and a glass of wine. We walked easily to town central for dinner. We had a delicious cocktail at Liam Ash. The server there was a wealth of information about bourbon culture. There are many great restaurants in town too. Paula is an excellent host and we hope to return soon - thank you!
Superhost
A wooden porch features several rustic chairs arranged for relaxation, with vibrant cushions adding comfort. The warm wooden texture of the walls complements the outdoor view seen through large windows. Natural light filters in, enhancing the serene ambiance of the space.
Cabin in Burnside
4.86 out of 5 average rating, 21 reviews

Relaxing escape

Gustavo AlexanderRating, 5 stars5 months ago
I don’t have words how describe this place, is to many things , I just want to said is 100 over 10.
Superhost
A rustic cabin is showcased with a sloped green metal roof and wooden siding. The front porch features seating arrangements of two chairs and a bench, creating a welcoming entry. Large windows allow natural light to illuminate the interior while an American flag adds character.
Cabin in Bronston
4.72 out of 5 average rating, 29 reviews

Tranquility Cabin

TriciaRating, 5 stars3 months ago
Comfortable and spacious for our party of 6! All beds were comfortable and everyone slept great. We loved the fire pit, Blackstone grill, and hot tub. Plenty of extras (coffee, spices, trash bags, detergents, etc). I love an owner that allows furbabies as we don’t leave our dog behind. We hiked some awesome trails in Daniel Boone National Forest. A great getaway!
Guest favorite
Home in Harrodsburg
4.94 out of 5 average rating, 18 reviews

The Luxe/Hot Tub/ King Beds/10 Mins Shaker Village

MikeRating, 5 stars6 months ago
everythi g there was awesome from the fire pit outback to the putting area to the Jacuzzis. had to figure out how to get on of them out of Eco mode, but after that everything was great.
Top guest favorite
A modern cabin is nestled among trees, with a snow-covered landscape creating a serene backdrop. The structure features multiple outdoor decks and illuminated pathways, enhancing the inviting appearance. Large windows reflect the surrounding nature, showcasing the home's integration with its tranquil environment.
Home in Jamestown
5 out of 5 average rating, 17 reviews

Onyx House

BobRating, 5 stars1 month ago
We stayed here for a weekend trip from out of state. Clean, Beautiful cabin. Peaceful and as described. Would love to bring the whole family back for another trip.
Guest favorite
An inviting deck area is highlighted by two comfortable chairs with blue cushions. A propane grill is positioned nearby, and a striped outdoor rug adds a touch of style. Lush greenery surrounds the space, creating a tranquil outdoor atmosphere.
Home in Nancy
5 out of 5 average rating, 10 reviews

The Shore Great Getaway

GraceRating, 5 stars1 week ago
Good location, exceptionally clean & well kept. Friendly neighbors and close to many attractions. Highly recommend and hope to stay again in the future. TV was exceptional and laundry facilities top notch. Very comfortable. Thank you for your hospitality
Guest favorite
Home in Lancaster
4.79 out of 5 average rating, 48 reviews

The Herrington

EthanRating, 5 stars8 months ago
Very Responsive. Friends and I had a great weekend
Top guest favorite
A gravel driveway leads towards a rustic farmhouse set among sparse trees and dry grass, framed by a wooden fence. The clear sky and distant building evoke a sense of calm in a rural setting.
Cottage in Berea
4.97 out of 5 average rating, 30 reviews

Country Cottage

AmyRating, 5 stars5 days ago
Our family loved our time at the country cottage. From sunrises to sunsets, the views and fresh air filled our cups. We were greeted by the sweetest barn cat. Our boys loved watching the cows come home and the tractors at work. The cottage floor plan made the home feel spacious. 10/10 we hope to stay again!

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Casey County
  5. Middleburg