House vacation rentals in Madison County

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Popular amenities for Madison County house rentals

House rentals with a pool

Top guest favorite
Home in Lexington
4.99 out of 5 average rating, 81 reviews

Close to Everything! Beautiful two-story home

BernardRating, 5 stars5 days 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 favorite
Home in Nicholasville
5 out of 5 average rating, 51 reviews

Cliff House

DavidRating, 5 stars5 days 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!
Guest favorite
Home in Lexington
4.93 out of 5 average rating, 27 reviews

My Old Kentucky Home

JacobRating, 5 stars2 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 favorite
Home in Lexington
4.97 out of 5 average rating, 115 reviews

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

GeorgeRating, 5 stars2 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 favorite
Home in Stanton
5 out of 5 average rating, 6 reviews

Hottub | Pool | Fire Pit | RV Parking | Hollerwood

JasonRating, 5 stars2 weeks ago
Thank you for allowing us to use the home. The family and I had a great time. Very peaceful, and relaxing. The creek and hot tub were great added bonuses. Still a little cold for the pool but that didn’t change the great time we had.
Top guest favorite
Home in Lexington
5 out of 5 average rating, 100 reviews

Game room! 5 beds an 4 bedrooms

AmandaRating, 5 stars1 week ago
Jeff was an outstanding host. He was quick to respond, shared helpful information, and was exceptionally accommodating. The home had many options for sleeping and the game room was a HUGE benefit, keeping both kids and adults entertained. The home is centrally located near restaurants, grocery stores and entertainment. I will definitely book again with Jeff!
Top guest favorite
Home in Sharpsburg
5 out of 5 average rating, 8 reviews

Firethorn’s Hilltop Haven

SunnieRating, 5 stars5 days ago
Beautiful place, out in the country. Pool was gorgeous and relaxing! Clean nice house! We would stay here again!
Guest favorite
Home in Georgetown
4.9 out of 5 average rating, 31 reviews

26 acre farm sleeps up to 30

DanRating, 5 stars1 month ago
This barndominium was a perfect spot for our group's annual golf trip. The living areas were incredibly spacious, the covered outdoor patio was a great size for hanging in the rain or sunshine, and there were plenty of beds on which to rest our heads. The property was well described and met all of our expectations, and its seclusion in the Kentucky horse fields added a memorable ambiance to the weekend. It was also nice to have easy driving access to Midway, Lexington, and even Louisville for a nice day trip. We would highly recommend this place to anyone gathering with a large group of friends or family.

Weekly house rentals

Top guest favorite
Home in Berea
4.94 out of 5 average rating, 563 reviews

Forest Street Cottage

KimberlyRating, 5 stars1 week 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 favorite
Home in Richmond
4.99 out of 5 average rating, 78 reviews

Southern Charm

NickRating, 5 stars2 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 stars2 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 stars3 weeks 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 favorite
Home in Berea
4.95 out of 5 average rating, 627 reviews

Traveler's Cottage

KathyRating, 5 stars3 weeks ago
Amy’s charming home was just what my daughter and I were looking for as part of our relaxing Kentucky getaway. The beds were comfortable, the art and colors used on the walls ,the furniture and the bedding were fun and whimsical, and we felt right at home. We spent a great deal of time on her cozy front porch reading on the comfortable rocking chairs. We loved how walkable the area was. We enjoyed walking through the Berea College campus and visited Native Bagel/Night Jar which was one of Amy‘s great suggestions. The artisan shops were close by. We would definitely come back again!
Top guest favorite
Home in Richmond
4.95 out of 5 average rating, 39 reviews

Bluegrass Comfort

AvaRating, 5 stars1 week ago
The house was amazing!!
Guest favorite
Home in Richmond
4.88 out of 5 average rating, 25 reviews

Frankie's Place

CaliRating, 5 stars2 weeks ago
Frankie’s place was the perfect place for my bridesmaids and I to stay the night before my wedding and also get ready in the day of! The space was so cozy, clean, and modern! We couldn’t have asked for a better place to stay! Definitely recommend for anyone looking for a place to stay in Richmond
Home in Nicholasville

Country Villa

JamesRating, 5 stars10 months ago
Our family had a wonderful time enjoying the pool, the privacy, and the beautiful country location of the property. The home was very clean and was well-stocked with everything that we needed. The outside area for grilling out and relaxing was the best. Maureen always responded quickly to any questions that we had. We could not have asked for anything more and look forward to coming back again. Thanks for sharing your home with us.

Private house rentals

Guest favorite
Home in Berea
4.94 out of 5 average rating, 206 reviews

Little House

NoahRating, 5 stars1 week 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 favorite
Home in Richmond
4.99 out of 5 average rating, 176 reviews

Richmond Retreat by Raydarr Properties, LLC

XavierRating, 5 stars1 week ago
Very nice place and clean. Very responsive host.
Top guest favorite
Home in Berea
4.96 out of 5 average rating, 127 reviews

Pinnacle Lodge now w/ Brand New Hot Tub!

NikkiRating, 5 stars2 weeks ago
Absolutely Beautiful home and views. fully stocked kitchen cabinets with pretty much everything in ur home including spices. All you need is food and clothes, everything else is provided. HIGHLY RECOMMEND!
Top guest favorite
Home in Berea
4.94 out of 5 average rating, 563 reviews

Forest Street Cottage

KimberlyRating, 5 stars1 week 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 favorite
Home in Berea
4.91 out of 5 average rating, 239 reviews

Churchill Cottage- Cheerful, Historic 1 Bedroom

PunkieRating, 5 stars3 weeks ago
Sweet Sweet place to stay. Our 2nd time to stay . Feels like home. The sunroom is my favorite area!. Lots of birds to watch and listen to. Peaceful and relaxing but close to town too. Highly recommend!
Top guest favorite
Home in Richmond
4.99 out of 5 average rating, 107 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 favorite
Home in Berea
4.95 out of 5 average rating, 627 reviews

Traveler's Cottage

KathyRating, 5 stars3 weeks ago
Amy’s charming home was just what my daughter and I were looking for as part of our relaxing Kentucky getaway. The beds were comfortable, the art and colors used on the walls ,the furniture and the bedding were fun and whimsical, and we felt right at home. We spent a great deal of time on her cozy front porch reading on the comfortable rocking chairs. We loved how walkable the area was. We enjoyed walking through the Berea College campus and visited Native Bagel/Night Jar which was one of Amy‘s great suggestions. The artisan shops were close by. We would definitely come back again!
Guest favorite
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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