House holiday rentals in Madison County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Madison County

House rentals with a pool

Top guest favourite
Home in Lexington
5 out of 5 average rating, 70 reviews

House w/private pool & hot tub, dogs ok

BetsyRating, 5 stars3 months ago
Better than expected. Fantastic and well-stocked kitchen - everything we needed for a full Thanksgiving feast. So many thoughtful details for a comfortable stay. Hot tub and backyard were awesome. Nice walkable neighborhood. Close to all things horses and handy to downtown. Highly recommend and will definitely stay again when in town.
Top guest favourite
Home in Lexington
4.99 out of 5 average rating, 77 reviews

Close to Everything! Beautiful two-story home

JamesRating, 5 stars2 months ago
It was a real home not the usual stuff you see on the apps. 2 fireplaces , huge outdoors and clean as could be. It was a perfect space inside and outside especially for the holidays. Definitely worth it.
Top guest favourite
Home in Lexington
4.96 out of 5 average rating, 103 reviews

LexFunZone! Pool! Hottub! GameRm! Keeneland/Derby!

JillRating, 5 stars2 weeks ago
Cozy house in a wooded cul-de-sac. Conveniently located in Lexington. House offered many amenities for my teenagers as we celebrated a Birthday. We all enjoyed the Game Room, Pool Table, Jacuzzi and beautiful backyard. Dining room table is a nice gathering spot for a family and the kitchen was perfect for preparing meals. Thanks Harrison!
Guest favourite
Home in Midway
4.99 out of 5 average rating, 80 reviews

The Bees Wing

MelanyRating, 5 stars4 months ago
We loved this Victorian home full of character! The beds were comfortable as were the gathering room couches. (Yes a new loveseat not shown in the pictures). The back porch was perfect for relaxing any time of the day and we used the table out there for meals too. We sat in the back yard to stargaze. The kitchen was extremely well stocked!! It is just delightful when a host/hostess takes the “B and B” part of this traditionally - with some breakfast items available! SO nice! 😊 We had some trouble with the shared bathroom not draining but were able to get it resolved. Great communication with our hosts! We loved the location- one block off the main strip of shops and restaurants in Midway! And as stated 15 - 20 mins to at least 3 distilleries, more cute shops in Versailles and to Keenland. Only about 30 mins into Lexington. Just perfect!
Top guest favourite
Home in Georgetown
5 out of 5 average rating, 13 reviews

Horse Country at The Palm House-Update Ranch home

AngieRating, 5 stars1 month ago
Jenni’s house was the perfect place to gather, relax and enjoy our family time in KY. Jenni should write a “How To” book for Airbnb hosts! Jenni started communication prior to our arrival which was not only helpful, but made me comfortable if/when I needed to reach out during our stay. Next, not only is this house perfectly decorated (looks exactly like the photos), but it is perfectly appointed as well! I have been to Airbnb’s that either have nothing or the absolute bare minimum with regard to things like, kitchen accessories…even utensils! NOT this house! We made three big dinners during our stay and we had EVERYTHING we needed to cook a full spread each time-there’s an air fryer, a crock pot, frying pans, cookie sheets, baking dishes, oven mitts (yes, I stayed in a house once that did not have oven mitts…and I didn’t even realize it until I needed to take something OUT of the oven). I could go on and on, and would, but I’m out of space. Thank you for an amazing stay!
Guest favourite
Home in Lexington
4.84 out of 5 average rating, 171 reviews

Silver Streak Ranch - Horse Hideaway

HannahRating, 5 stars5 months ago
Loved our stay at Deb’s. Excellent location and tons of amenities! Huge plus for being pet friendly. Our pup felt right at home!
Guest favourite
Home in Stanton
5 out of 5 average rating, 12 reviews

Maple Place

EricaRating, 5 stars4 months ago
We had a great stay! House was beautiful and roomy. We will definitely stay again
Top guest favourite
Home in Lexington
5 out of 5 average rating, 89 reviews

Game room! 5 beds an 4 bedrooms

LeahRating, 5 stars2 weeks ago
We were traveling for volleyball. Great location if playing at Central Bank Center. Literally around the corner from plenty of shopping. The house is in a safe, quiet neighborhood. The house itself was great. We particularly liked the cleanliness. Very usable kitchen. Big enough for our group of 5 to have breathing room. Jeff was so accommodating to even mail back a pair of shoes my teenager left behind. We will not hesitate to stay here the next time we are in Lexington!

Weekly house rentals

Top guest favourite
Home in Richmond
4.98 out of 5 average rating, 66 reviews

Southern Charm

AmberRating, 5 stars4 days ago
Great home and wonderful host. It was perfect for us siblings to stay and reconnect. Would definitely book again. Thanks!!
Superhost
Home in Berea
4.64 out of 5 average rating, 33 reviews

Lovely Laurel

JohnRating, 5 stars3 months ago
Location was great to the shopping area and several good places to eat. Close to renfro valley were we saw Rhonda Vincent and the rage. The place was clean and had all we needed for our stay. You are always going to find things that you might do differently but not everyone has the same expectations. They have done a real good job in trying to bridge that gap and provide a comfortable place to stay. We recommend it for anyone looking. We rate it five stars !!!
Guest favourite
Home in Richmond
5 out of 5 average rating, 12 reviews

Frankie's Place

JeffRating, 5 stars1 week ago
Loved this house it was very beautiful on the inside…beds are amazing and the TV are great!!! Loved it here I highly recommend it to anyone!!!
Top guest favourite
Home in Richmond
4.99 out of 5 average rating, 100 reviews

Stylish Richmond Home. Near EKU and Downtown

SaraRating, 5 stars1 month ago
My family and I loved staying @ Jamie’s property while visiting my daughter who attends EKU! The property was well maintained had everything we needed to make our Galentine’s weekend the best! We will try to book the same property when we visit in the spring!
Superhost
Home in Richmond
New place to stay

Heart of Richmond

RubenRating, 5 stars4 weeks ago
This place was by far the best and prettiest I’ve ever been in

Private house rentals

Guest favourite
Home in Berea
4.94 out of 5 average rating, 201 reviews

Little House

AmandaRating, 5 stars3 months ago
so glad we finally made it! this was a lovely place to stay! the views were spectacular and star watching at night was wonderful! loved the fact that it was just a perfect drive to Berea so getting things are going out to dinner wasn't a big deal! would happily stay again.
Top guest favourite
Home in Richmond
4.99 out of 5 average rating, 164 reviews

Great older home by Raydarr Properties, LLC

JuliaRating, 5 stars1 week ago
We used Harold’s place as a quick stopover on our return to Michigan, so we didn’t get to take full advantage of a really nice older home. We will definitely keep this home on our list as a place to return to in the future.
Top guest favourite
Home in Berea
4.94 out of 5 average rating, 540 reviews

Forest Street Cottage

RaymondRating, 5 stars1 day ago
This is the second cottage of Amy's that we have stayed in and they are a great bargain! Amy has done a great job of decorating each home and providing all the amenities that are needed. Both are in great spots that allow for privacy but also are located in very walkable neighborhoods with access to restaurants and shopping. Amy has been proactive in communication and responds immediately.
Top guest favourite
Home in Berea
4.96 out of 5 average rating, 119 reviews

Pinnacle Lodge now w/ Brand New Hot Tub!

WindyRating, 5 starstoday
This Airbnb was everything we hoped for and more! Tucked away on a gorgeous property but just a few miles from town, it gave us the best of both worlds—peaceful and private, yet super convenient. It had every amenity we could possibly need, and it was spotless (which is always a big deal for us!). The bed? A Tempur-Pedic with top-notch linens—so comfortable we could’ve slept in all day. There was plenty of space to spread out, relax, and just enjoy the surroundings. We only stayed two nights, but honestly, we could’ve easily stayed longer. We didn’t have time to try out the hot tub, but that just means we’ll have to come back. And a big shoutout to Austin—super responsive and great to work with. If you’re heading to Berea, don’t even think twice—this is where you want to stay!
Guest favourite
Home in Berea
4.91 out of 5 average rating, 228 reviews

Churchill Cottage- Cheerful, Historic 1 Bedroom

AnnetteRating, 5 stars4 days ago
We had a lovely stay at Alison’s cottage in Berea. We enjoyed the walkability and the options for food and artisan shops in the area. The house was very, very cute and cozy. The beds were comfortable and the kitchen was well stocked with dishes for drinks and cooking. We ate out most of the time but enjoyed coffee in the morning. Small detail but there were ice cubes ready for us when we prepared our drinks in the evening. We had forgotten to buy ice and were happy that small detail was ready. My favorite part of the house is the little office/sunroom area. I had my coffee there in the morning and watched the rain. Great location and great communication. Will stay in the future when we come to Berea.
Guest favourite
Home in Berea
4.95 out of 5 average rating, 610 reviews

Traveler's Cottage

AbbyRating, 5 stars4 days ago
Amy was a wonderful host and was super sweet! She was extremely helpful and so knowledgeable about the area. Her home was gorgeous and cozy.
Top guest favourite
Home in Richmond
4.9 out of 5 average rating, 180 reviews

Downtown - walk to EKU, town and parks. Near I-75

VictoriaRating, 5 stars3 weeks ago
We had a lovely time staying in this very nice home. It was spotless and very well stocked. The beds were comfy (which is very important!), and there were many spots to rest and relax. You can’t beat the closeness to campus, and there are great restaurants a short walk away. I highly recommend this AirBnB.
Guest favourite
Home in Berea
4.88 out of 5 average rating, 121 reviews

Big Hill House

CarolineRating, 5 stars5 months ago
Nathan and Shannan’s place was just lovely. Just a few minutes out of town and such a unique home with lots of love built in. We had a lovely stay and as a proud Berea College alum, I loved seeing some old Berea memorabilia in the home. Very cozy for a beautiful fall weekend with my family! And my chihuahuas were happy too!

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