House holiday rentals in Madison County

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Popular amenities for Madison County house rentals

House rentals with a pool

Top Guest favourite
Home in Lexington
4.99 out of 5 average rating, 82 reviews

Close to Everything! Beautiful two-story home

BernardRating, 5 stars2 weeks ago
This home and it's surroundings are absolutely beautiful! We had a family vacation and had a wonderful time! The pool was amazing and each room of the house was modern and elegant at the same time. Our grandchildren also loved watching the ducks in the little creek. We usually go to the ocean but were looking for something a little closer to home this year (3 hours away) and we were certainly not disappointed! We highly recommend it and will be back some day! Thank you, Kathy! Benson & Diane Bedel & Family
Top Guest favourite
Home in Nicholasville
5 out of 5 average rating, 51 reviews

Cliff House

DavidRating, 5 stars2 weeks ago
The Cliff House is a wonderful house that has many amenities. We loved the environment, the spaciousness, the pool. The kitchen has everything we needed. We had a wonderful stay. It requires a drive to anywhere. Angela was very responsive and provided suggestions when asked. Very helpful!
Superhost
Home in Lexington
4.64 out of 5 average rating, 44 reviews

Private for 4 No cleaning fee Discounts up to 20%

ChaseRating, 5 stars2 weeks ago
Couldn’t be any happier with my stay here. Exactly what my friends and I needed for our trip. Sherrie was extremely helpful with recommendations and was a great host. Would definitely stay here if I ever come back to Lexington.
Guest favourite
Home in Lexington
4.89 out of 5 average rating, 28 reviews

My Old Kentucky Home

JacobRating, 5 stars3 weeks ago
My Old Kentucky Home hosted by Shane was a wonderful place to stay! The neighborhood was beautiful and quiet. The amenities on site were amazing. The hot tub and pool were all set and ready for our group when we arrived, which we appreciated greatly. Communication was great, and Shane was on top of everything. Our stay was wonderful and we would love to come back for another visit! Would recommend to anyone looking to stay in the Lexington area.
Top Guest favourite
Home in Lexington
4.97 out of 5 average rating, 115 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

GeorgeRating, 5 stars4 weeks ago
Harrison was an amazing Host! The house was immaculate and had everything you could want to feel at home and relax. This is a premier spot to take your family for Visiting the gorgeous and historic Lexington. Thank you so much for an amazing place to gather as we celebrated our son’s graduation.
Guest favourite
Home in Stanton
5 out of 5 average rating, 8 reviews

Hottub | Pool | Fire Pit | RV Parking | Hollerwood

JoanneRating, 5 stars1 week ago
The AC went out. The host/ co host responded immediately. Grateful for their response. It was back on in no time. A lovely house. We would definitely rent it again.
Top Guest favourite
Home in Lexington
5 out of 5 average rating, 102 reviews

Game room! 5 beds an 4 bedrooms

StephanieRating, 5 stars1 week ago
This place was very nice and Jeff was a terrific host! Perfect for a nice family getaway. Close to everything. If you are looking for fun and relaxation, this is the house. Game room was a huge bonus with 2 arcade games and several board games. The backyard is so cute, private and cozy. Kitchen was stocked with coffee and everything you need and the beds were comfy. This is a must stay. Very cute house! Loved it!
Top Guest favourite
Home in Sharpsburg
5 out of 5 average rating, 9 reviews

Firethorn’s Hilltop Haven

NormaRating, 5 stars1 week ago
Me and my family had a wonderful time during our stay here , we will definitely be coming back when available 🙏 the house is beautiful and the pool is so nice . We definitely recommend to stay here . We were here for two nights and the hosts were so welcoming and polite . So excited to come back soon !!

Weekly house rentals

Top Guest favourite
Home in Berea
4.94 out of 5 average rating, 564 reviews

Forest Street Cottage

KimberlyRating, 5 stars2 weeks ago
Amy’s cottage is comfortable and cute, and an easy stroll over to Berea College. Amy is responsive and easy to work with—we would stay there again.
Top Guest favourite
Home in Richmond
4.99 out of 5 average rating, 79 reviews

Southern Charm

NickRating, 5 stars3 weeks ago
Great place for a group of four to stay while playing golf in the area.
Superhost
Home in Berea
4.65 out of 5 average rating, 34 reviews

Lovely Laurel

ElizabethRating, 5 stars3 weeks ago
We had a wonderful stay there. Super comfy beds and a really nice neighborhood that we were able to explore. Laura and Laurel were also helpful when we needed anything. Thumbs up all the way!
Superhost
Home in Richmond
4.75 out of 5 average rating, 4 reviews

Richmond Gem

KeenaRating, 5 stars1 month ago
We were in town for our sons graduation with family. The home was easy to find, spacious and beautifully decorated. Would highly recommend !
Top Guest favourite
Home in Berea
4.95 out of 5 average rating, 630 reviews

Traveler's Cottage

MerryRating, 5 stars1 week ago
This home located just up the road from Berea College campus is clean, spacious. and in peaceful surroundings. Lovely wood finishes and artful decor. Steps to enter front and lack of walk-in shower to be considered for individuals with mobility concerns. Would book again if in area.
Top Guest favourite
Home in Richmond
4.95 out of 5 average rating, 40 reviews

Bluegrass Comfort

AvaRating, 5 stars2 weeks ago
The house was amazing!!
Guest favourite
Home in Berea
4.9 out of 5 average rating, 59 reviews

Martin House at Happiness Hills Farm

RachelRating, 5 stars14 months ago
Friendly owners. Helpful with all our questions and requests. Fun lodging for the kids! And relaxing for the parents!
Guest favourite
Home in Richmond
4.89 out of 5 average rating, 27 reviews

Frankie's Place

SaraRating, 5 stars2 weeks ago
Sherri’s property was fantastic—absolutely the perfect base camp for our wedding weekend in Richmond! The home was well-stocked, the beds were incredibly comfortable, and it’s located in a quiet, lovely neighborhood. We had easy access to the freeway, grocery stores, and great restaurants. Sherri was incredibly responsive and helpful throughout our stay. We would absolutely stay here again!

Private house rentals

Guest favourite
Home in Berea
4.94 out of 5 average rating, 207 reviews

Little House

NoahRating, 5 stars2 weeks ago
Beautiful place! we had a great time, it was very relaxing! the mountain views around the area were breathtaking! the cabin was cute and very comfortable. we had fun watching wildlife outside too, had a curious raccoon come say hello by the deck window 😄 and the hosts were friendly and very helpful with a house guild of things to do around the area. 10/10 great time!
Top Guest favourite
Home in Richmond
4.99 out of 5 average rating, 177 reviews

Richmond Retreat by Raydarr Properties, LLC

TarekRating, 5 stars1 week ago
Arnold Place was an exceptional stay! The location was quiet, serene, and exactly as described. The apartment was comfortable, well-maintained, and had all the amenities we needed. Our host was incredibly helpful, responsive, and made sure we had everything for a smooth stay. It's the perfect spot for a relaxing getaway. Highly recommend to anyone visiting Eatern Kentucky university or the area. Thank you for providing such a wonderful experience Arnold! ⭐️⭐️⭐️⭐️⭐️
Top Guest favourite
Home in Berea
4.96 out of 5 average rating, 128 reviews

Pinnacle Lodge now w/ Brand New Hot Tub!

AlexRating, 5 stars2 weeks ago
A very wonderful place that we would love to come back to in years to come. We are very grateful for Austin & the time away from our normal lives that his property gave us and the memories made.
Top Guest favourite
Home in Berea
4.94 out of 5 average rating, 564 reviews

Forest Street Cottage

KimberlyRating, 5 stars2 weeks ago
Amy’s cottage is comfortable and cute, and an easy stroll over to Berea College. Amy is responsive and easy to work with—we would stay there again.
Guest favourite
Home in Berea
4.91 out of 5 average rating, 240 reviews

Churchill Cottage- Cheerful, Historic 1 Bedroom

BrandyRating, 5 stars2 weeks ago
This was a great and affordable place to stay in Berea. It was super cozy with lots of amenities. Walkable to downtown restaurants and shops, but private and safe. A short drive to Pinecroft woodworking school. Would stay again on my next trip.
Top Guest favourite
Home in Richmond
4.99 out of 5 average rating, 108 reviews

Stylish Richmond Home. Near EKU and Downtown

AbbyRating, 5 stars1 month ago
Jamie was incredible! She is very kind and communicative. We had a very short stay but the house was very clean and very nice and in a great neighborhood.
Top Guest favourite
Home in Berea
4.95 out of 5 average rating, 630 reviews

Traveler's Cottage

MerryRating, 5 stars1 week ago
This home located just up the road from Berea College campus is clean, spacious. and in peaceful surroundings. Lovely wood finishes and artful decor. Steps to enter front and lack of walk-in shower to be considered for individuals with mobility concerns. Would book again if in area.
Guest favourite
Home in Richmond
4.89 out of 5 average rating, 187 reviews

Downtown Charm - Walk to EKU & Parks Near I-75

CraigRating, 5 stars1 month ago
Great place to stay in a quiet neighborhood. Very close to anything you might need. Host was very responsive and helpful.

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