House vacation rentals in Woodford County

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Popular amenities for Woodford County house rentals

House rentals with a pool

Top guest favorite
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
Superhost
A spacious living area is centered around a decorative stone fireplace, complemented by a large flat-screen television mounted above. Comfortable leather seating and a wooden coffee table are arranged on a patterned area rug, with natural light entering through a nearby window.
Home in Lexington
4.89 out of 5 average rating, 28 reviews

My Old Kentucky Home

JacobRating, 5 stars1 month 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.
Superhost
A spacious outdoor area features a rectangular pool surrounded by a concrete patio. A slide is positioned at one end of the pool, while lounge chairs and a table with umbrellas provide shaded seating nearby. The two-story home, with various windows, overlooks the pool.
Home in Lexington
4.64 out of 5 average rating, 45 reviews

Private for 4 No cleaning fee Discounts up to 20%

BrittanyRating, 5 stars3 days ago
Sherrie was a great host and we enjoyed our stay at the hidden gem! She has gone out of her way to make her space full of amenities and comfortable. The large living area in the basement was nice to relax in and we enjoyed looking at the available books and games. Our space was clean and the upstairs bed was extremely comfortable! The neighborhood is quiet with lots of convenient stores and restaurants. Only small downside of the property is that it is a shared space so there is some sound carryover. Sherrie was respectful and friendly when we crossed paths! Loved her great communication! Overall a great stay, we would come back!
Top guest favorite
An aerial view of the rustic country home showcases a spacious outdoor area. A round above-ground pool is situated prominently among the green lawn, surrounded by wooden decking. Nearby, several tables and a picnic space are visible, inviting relaxation and gatherings in a tranquil setting.
Home in Frankfort
4.98 out of 5 average rating, 62 reviews

MacAttie Acres

TriciaRating, 5 stars1 week ago
Well, our group of 9 had an enjoyable time in this home! It was as advertised and extremely clean, comfortable and quiet. Cindy was just the sweetest and most respectful host always available to answer questions or give recommendations. Close to great distilleries and downtown Frankfort with cute shops and dining. The pool and hot tub were clean and working and the home was well stocked with basic necessities. Highly recommended and can't wait to come back!
Top guest favorite
A bright and inviting outdoor area features a refreshing swimming pool with clear blue water. Surrounding the pool are sun loungers and a shaded gazebo, set against a backdrop of lush trees and well-maintained landscaping.
Home in Lexington
4.97 out of 5 average rating, 116 reviews

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

NicoleRating, 5 stars3 days ago
This home was amazing. The pool was great and exactly as described. Harrison was a great host!!
Top guest favorite
A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.
Home in Midway
4.99 out of 5 average rating, 88 reviews

The Bees Wing

JessieRating, 5 stars1 week ago
We went for a girls weekend it was the perfect get away! The screened on in porch was our save haven for the weekend . So peaceful and loved walked to downtown areas .
Top guest favorite
A refreshing pool is surrounded by a wooden deck, featuring lounge chairs and a table with an umbrella. Floating toys are visible in the clear water, while lush greenery and trees provide a natural backdrop to the inviting outdoor space.
Home in Lexington
5 out of 5 average rating, 102 reviews

Game room! 5 beds an 4 bedrooms

StephanieRating, 5 stars2 weeks 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!
Superhost
A dual-level deck houses an above-ground swimming pool with clear blue water. Two custom wooden chairs provide seating near the pool's edge, framed by a brown fence and lush greenery in the background. The deck surface is finished in light grey, enhancing the outdoor space.
Home in Lawrenceburg
4.81 out of 5 average rating, 166 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

SuzanneRating, 5 stars3 days ago
Fantastic stay at this beautiful home. Hot tube and pool were clean and were very accessible. Kitchen and grill were also clean and easy to use. Every part felt very homey and comfortable. This is a great place to stay for all things Bourbon Trail because it’s very centrally located.

Weekly house rentals

Top guest favorite
The exterior of the cottage is framed by lush greenery, highlighting its rustic wooden facade. A red umbrella provides shade over the entrance, while an American flag adds a patriotic touch. A driveway leads to off-street parking beside the structure.
Home in Midway
4.96 out of 5 average rating, 78 reviews

The Cottage

AllisonRating, 5 stars2 months ago
We had a wonderful stay at Steve’s house in Midway. The house is SO charming… even more so than the pictures convey. Perfectly outfitted, totally comfy and the perfect location for a fun weekend of Keeneland racing and Midway dining (be sure not to miss Holy Hill Inn and Heirloom for two of the best dining experiences you’ll ever have!). The location is both convenient and beautifully picturesque. Don’t pass this one up! You won’t regret it!
Guest favorite
The historic home features a yellow exterior with subtle white trim, outlined by mature trees and manicured shrubs. A wide brick pathway leads to the front entrance, accentuated by a spacious porch with several windows and decorative elements. The two-story structure embodies classic architectural charm.
Home in Versailles
5 out of 5 average rating, 5 reviews

Near Keeneland and on Bourbon Trail Lexington area

MelissaRating, 5 stars1 week ago
The photos do not do this home justice, it is beautiful and still very true to the era it was built while having upgraded amenities. Check-in was easy. Janie is very friendly and has thought of everything you might need on your stay. It feels like home right when you walk in. The rooms are super spacious and comfy and the whole house was spotless. Downtown is only a short walk with some shops and good restaurants. We loved our stay and would definitely recommend this home.
The kitchen features a central island crafted from wooden barrels, complemented by modern stainless steel appliances. Open shelving displays glassware. Light bamboo flooring enhances the space, while a cozy living area with a soft grey sofa and patterned rug is visible in the background.
Home in Midway
5 out of 5 average rating, 25 reviews

Bit and Bourbon

KrisRating, 5 stars26 months ago
Great place to stay if you are in town for Bourbon, wine and horses! Host gave us great recommendations on places to visit and eat. They had all the essentials for us. Less than a block away from downtown Midway with plenty of great places to eat. Will definitely be back!
Top guest favorite
A spacious living area features a comfortable leather sofa with patterned throw pillows, complemented by a round coffee table. Nearby, a dining table accommodates four, and large windows provide natural light, showcasing a serene outdoor view. The decor includes earthy tones and textures.
Home in Midway
5 out of 5 average rating, 17 reviews

Cottage in horse country!

DeniseRating, 5 stars1 month ago
We were in town to attend 3 Day Event at Kentucky Horse Park . We enjoyed our stay, loved the porch and comfortable furniture and beds. Kitchen was very well stocked and large dining table allowed for us to all gather for meals and enjoy cards at the end of our day. Being all horse people, we so loved seeing the surrounding farms with mares and their foals. Close by restaurants, Wallace Station and Barrel and Brown were great as well as Midway Bakery for homemade bread and quiche. Hope to return some time!
A cozy living area is highlighted by a soft sectional sofa arranged around a wooden coffee table. A stone fireplace serves as the focal point, complemented by a flat-screen TV mounted above. Large windows allow natural light to fill the space, enhancing its inviting feel.
Home in Frankfort
4.91 out of 5 average rating, 11 reviews

Spacious Frankfort Retreat on Bourbon Trail!

StevenRating, 5 stars1 month ago
Perfect location for Bourbon Trail, very close to Buffalo Trace.
A sunroom features a comfortable blue sofa adorned with decorative pillows. Two poufs provide additional seating. Lush plants are placed around the space, while large windows allow natural light to fill the room. Framed botanical prints decorate the white brick walls.
Home in Versailles
4.88 out of 5 average rating, 17 reviews

Historic Sugar Hill Farm w/ Pool! Incredible View!

LoriRating, 5 stars2 weeks ago
Beautiful home and property! It was perfect for our annual girl's weekend! The weather kept us inside more than we had hoped, but we did get a couple of sunny hours to enjoy the pool. Even when the rain kept us indoors, there was plenty of room to just relax and enjoy each other's company. There were plenty of windows to keep us connected to the outdoors and the view was perfect from every direction. Rolling green pastures speckled with horses! Very private! Highly recommend!
A charming farmhouse is framed by lush green pastures and a rustic black wooden fence. Trees dot the landscape, providing natural beauty against a cloudy sky. A gravel path leads up to the house, enhancing the inviting rural setting.
Home in Lexington
4.89 out of 5 average rating, 18 reviews

Malcomb Farm

ConnieRating, 5 stars14 months ago
We LOVE this home! I was there on business and my tram and myself stay at this home and it was the perfect place to come back to after a busy day! The host was wondereful and helpful! We even say horses in the field across the way
Top guest favorite
A collection of five framed portraits is arranged on a bright green wall. Below, a cozy orange couch is complemented by a textured throw blanket in a gradient of blue and green hues. A wooden coffee table is partially visible, enhancing the warm atmosphere.
Home in Lexington
5 out of 5 average rating, 31 reviews

CINDERELLA'S GUEST HOUSE

NicoleRating, 5 stars1 month ago
The place was lovely and everything we expected from the posting. Beautiful natural lighting and homey feel.

Private house rentals

Top guest favorite
The outdoor space features a DIY pickleball court, surrounded by well-maintained grass and bordered by planters. A gazebo and hot tub are visible adjacent to the brick house, while tall trees provide a serene backdrop to the inviting courtyard area.
Home in Midway
5 out of 5 average rating, 37 reviews

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

AbbeyRating, 5 stars4 days ago
This is our second time here. Even better this time! We’ve been in the winter and now in the summer. I brought the kids down and they have so much fun. We went horse back riding and drove down to red river gorge for a day too. Lots to do and beautiful.
Top guest favorite
A charming cottage exterior is framed by a large tree, with a well-maintained lawn and shrubs lining the front. The entrance features a porch with a welcoming door and matching window shutters, all under a sloped metal roof.
Home in Midway
4.99 out of 5 average rating, 128 reviews

Country Cottage in Horse and Bourbon Country

DanaRating, 5 stars1 week ago
Awesome place! Clean, updated, and modern. The thing that set it apart from any other AirBNB that I have stayed at were all of the amenities that were included. Snacks and drinks waiting for us were an unexpected and welcome surprise. Thanks!
Top guest favorite
A bright living area features a comfortable gray sofa adorned with colorful throw pillows. A round coffee table sits atop a soft area rug, complemented by wooden chairs nearby. Natural light streams through multiple windows, creating a welcoming atmosphere in this open space.
Home in Frankfort
5 out of 5 average rating, 164 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

LeaRating, 5 stars2 weeks ago
Great home, very well maintained, friendly responsive host nearby, so much to do, the road is a bit busy out front but the backyard is peaceful and private, great restaurants and places to explore within a short distance
Superhost
A cozy living area features two large sofas, complementing a rustic wooden coffee table. The space is illuminated by a floor lamp next to one sofa. Artwork, including butterfly prints and nature scenes, decorates the walls, while a patterned area rug adds texture.
Home in Versailles
4.84 out of 5 average rating, 89 reviews

Woodford Stables / Walk to Eckert's Orchard

MasonRating, 5 stars3 weeks ago
great place and very nice host will definetly stay again
Top guest favorite
An open-concept living area features comfortable seating arranged around a circular rug. A well-equipped kitchen is visible in the background, complemented by a dining table for four. Natural light enters through multiple windows, creating a bright and welcoming atmosphere.
Home in Versailles
4.97 out of 5 average rating, 37 reviews

Willow Springs 2br/1ba- Sleeps 8 33 acres w/trails

StaceyRating, 5 stars1 month ago
The place was so homey!!! The trails were fun to walk and see the flowers and butterflies. Location is great! Close to SO many things!!! Will stay here again for sure!
Top guest favorite
Home in Versailles
5 out of 5 average rating, 7 reviews

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

JamesRating, 5 stars6 days ago
Place was amazing! John was responsive and recommended some local restaurants that were great! Close to distilleries. Beautiful country. The hot tub controls are on the back "under the cover once you open it". Maybe the bourbon didn't help us lol. Golf simulator was a blast! We actually cut our evening short to go back to the place and hang out! Don't miss this special gem!
Top guest favorite
A charming, two-story house is nestled between two large trees, with a wide lawn surrounding it. The home features a porch area and is partially shaded, while warm sunlight casts a long shadow across the grassy yard. A serene, rural setting is highlighted by a wooden fence in the background.
Home in Versailles
4.95 out of 5 average rating, 187 reviews

Quaint little farm house close to Keeneland/horses

LaurieRating, 5 stars3 days ago
Our stay was very enjoyable and everything we needed for the weekend. We were close to Lexington, but the location is quiet and relaxing. The view is beautiful with pastures, horses, and picturesque sunsets.
Guest favorite
The image captures a serene view along the Kentucky River. Tree branches frame the scene, with some trees showing signs of early spring. The calm, green water reflects the surrounding landscape, creating a peaceful natural environment.
Home in Kentucky
4.9 out of 5 average rating, 111 reviews

The Stagg House on the Ky River

ChristopherRating, 5 stars2 months ago
Myself and three friends stayed at the Stagg House during our visit to the bourbon trail. Private and peaceful location along the Kentucky river. Perfect place to stay during our visit to the area.

Destinations to explore