House holiday rentals in Frankfort

A dining area features a round wooden table set with glassware and green accents. A striking mural of bourbon barrels lines one wall, illuminated by a modern pendant light, while a doorway leads to other spaces in the home.

5 out of 5 average rating, 107 reviews

*Long Pour: Your Luxury Downtown Bourbon Home*

Welcome to bourbon heaven. Really. 🥃 Long Pour is located in the heart of Frankfort and bourbon country, - walking distances from Buffalo Trace, downtown restaurants, bars, and historic neighborhoods. Our place is a luxury home away from home featuring two bedrooms, an iconic shower, free parking, and not to mention the bourbon features all throughout the home. No matter your reason for visiting Frankfort, this home is the perfect getaway to enjoy the best of Kentucky. Can't wait to host y'all!

4.96 out of 5 average rating, 373 reviews

A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.

Home in Lexington

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

4.97 out of 5 average rating, 164 reviews

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

The modern kitchen showcases white cabinetry and stainless steel appliances. A central island with seating is complemented by decorative pendant lights overhead. Natural light brightens the space, highlighting the elegant granite countertops and a small decorative plant on a wooden tray.

4.95 out of 5 average rating, 172 reviews

The Julep - Cozy yet spacious, near local hotspots

Families or groups will love the open & welcoming floor plan that makes it easy for all to spend time together OR a quiet moment alone. Restaurants, shopping, Bourbon tours, family entertainment, canoe, river & nature trails are only a short drive away. Situated between Lexington & Louisville, "The Julep" allows you to explore Kentucky while staying in the charm of the Capital City. Newly renovated 5BR/3BA, "The Julep" is ideal for a short or long term stay, whether it's for work or play.

A modern kitchen is showcased, featuring stainless steel appliances and white cabinetry. The spacious marble countertop is complemented by decorative elements, including teal accents. A cutting board rests on the counter while colorful artwork adorns the wall, adding a touch of vibrancy to the space.

4.95 out of 5 average rating, 239 reviews

Lil Bit O' History on Main- Historic Downtown!

Built in 1867, with original deed of 1813, this beautiful piece of Frankfort's history has been fully restored! This cozy shotgun home offers magnificent views of the State Capital in front and of the Old Capital from the side! Located along the Bourbon Trail, it offers a short walk to BOM, local breweries, downtown coffee at Kentucky Coffee Tree, and all the shops of Broadway. The History Center is close, as is The Kentucky Military Museum. Buffalo Trace and Castle and Key are minutes away.

A game room is presented with a pool table at its center, surrounded by wooden flooring. A vintage slot machine and an air hockey table are visible against a wall. Natural light enters through a window covered by sheer curtains, and a flat-screen TV is mounted on an adjacent wall.

4.88 out of 5 average rating, 115 reviews

Bourbon Trail Downtown Frankfort w/Game Room

Close to several Bourbon Distilleries, Buffalo Trace, Keeneland, and breweries. Home has kitchen, dining room, living room, game room, bathrooms, laundry, outdoor space, and private bedrooms. The bedrooms have a tv, king bed, dresser & sofa. Futon and kids table located in one bedroom. Downtown Frankfort is a scenic 20 minute walk along the river and hosts an active scene of local restaurants, bars, shops & history. This house has everything you need for a fun enjoyable stay! #BourbonTrail

A welcoming view of The Spencer cottage is presented, showcasing lush greenery and carefully tended landscaping. A sign is positioned in the foreground, displaying the name of the property. The brick exterior of the cottage is framed by trees, enhancing its charming appeal.

4.9 out of 5 average rating, 131 reviews

Frankfort’s Capitol view cottage

Frankfort's Capitol View Cottage Named for architect Spencer Cryer, the Spencer offers a unique charm with the comforts of home on your central Kentucky travels. An off the beaten path yet still downtown cottage with a seasonal view of the Capitol, the home offers both inside and outside amenities. Steps from the Capitol grounds and 20 miles to Lexington 50 miles to Louisville and within an hour drive of at least 10 distilleries on the Bourbon Trail including Buffalo Trace a local favorite!

The exterior of the home features a welcoming porch with rocking chairs framed by neatly trimmed hedges. A manicured lawn with shrubs enhances the inviting approach to the entrance. Surrounding trees provide a natural backdrop, contributing to the overall charm of the property.

4.94 out of 5 average rating, 196 reviews

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

Wake up & smell the mash! Located just steps away from Buffalo Trace Distillery. Enriched with history & tradition is where you will find Wilkinson. This historic home has recently undergone renovations & no expense was spared. Guests will enjoy the walkability to Downtown Frankfort & many of the local attractions. Featuring 2 bedrooms & 2 baths, guests are able to experience life like a local with all the modern-day amenities. We are also only a 7.2-mile drive to Castle & Key Distillery.

4.97 out of 5 average rating, 702 reviews

The entrance to the historic Buffalo Springs Distilling Company is showcased, featuring sturdy stonework and a wooden door. A sign hangs above the entrance, indicating the building's name. Nearby, green grass is visible, hinting at the surrounding area.

Home in Stamping Ground

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

4.98 out of 5 average rating, 112 reviews

A charming cottage exterior is framed by lush greenery and mature trees. The light gray siding is complemented by white columns at the entrance. A brick walkway leads to the front door, bordered by neatly manicured bushes and seasonal flowers.

Home in Georgetown

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our 3 newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

A spacious living area features a plush blue sofa and two vibrant yellow chairs. A flat-screen TV is positioned on a white console. Natural light filters through multiple windows, illuminating a decorative area rug placed on the warm wood flooring.

4.95 out of 5 average rating, 102 reviews

Whiskey Woods: Newly Remodeled w/ HOT TUB!

Discover Whiskey Woods in picturesque Frankfort, KY! This 3-bed, 2-bath retreat on 3.6 acres offers modern amenities. Enjoy open-concept living, a fully equipped kitchen, and outdoor dining. Explore the lush property with grill. Sleep in plush beds, including a king-sized Whiskey Suite. Stay connected with Wi-Fi, laundry, and parking. Only 1.4 miles from Castle and Key Distillery, and 4.9 miles from Woodford Reserve. Minutes from downtown attractions. Book your Frankfort getaway today!

4.95 out of 5 average rating, 220 reviews

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Popular amenities for house rentals in Frankfort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.99 out of 5 average rating, 83 reviews

MacAttie Acres

4.97 out of 5 average rating, 131 reviews

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

Home in Lexington

Lexington Holiday FUN-ZONE! Pool! Hottub! GameRm!

5 out of 5 average rating, 119 reviews

A cozy living area is highlighted by a fireplace and large windows allowing natural light. A round coffee table is positioned at the center of a comfortable seating arrangement that includes a sectional sofa and armchairs. Potted plants add a touch of greenery.

Home in Prospect

Peppermint Cottage Norton Commons w Breakfast

4.95 out of 5 average rating, 20 reviews

Home in Bloomfield

Luxury Estate: Bourbon Room, Sauna, Spa, & Cinema!

4.98 out of 5 average rating, 132 reviews

Home in Lexington

Game room! 6 beds 2 baths

5 out of 5 average rating, 4 reviews

Unique YEAR-ROUND Pool + Hibachi Grill + Game Room

4.88 out of 5 average rating, 125 reviews

A welcoming front porch is presented, featuring two blue rocking chairs flanking a small table. Lush green bushes and colorful plants are visible. The porch leads to a red door, surrounded by large windows that reflect natural light and the scenic surroundings.

Home in Taylorsville

Kentucky Sunrise 18- Greet the Sun As it Rises

4.98 out of 5 average rating, 113 reviews

The entrance of the modern home is framed by neatly trimmed hedges and colorful flower pots. A decorative walkway leads up to large glass doors, providing an inviting glimpse into the interior.

Home in Georgetown

Modern Farmhouse/20 acres/9 miles from Horse Park

Weekly house rentals

4.98 out of 5 average rating, 54 reviews

A modern rural structure is showcased with a spacious wooden deck that extends across the front. String lights are suspended above, adding a soft glow. The surrounding landscape features a grassy area and a black wooden fence, with trees in the background.

Home in Shelbyville

The Back 40 ~ Modern*Scenic*Convenient*EV Charger

The exterior features a charming white and wood panel facade with a covered porch. Two entry doors are framed by large windows, inviting natural light. A small seating area includes a sleek bench and two chairs, positioned on a textured rug amidst a landscaped pathway.

4.93 out of 5 average rating, 94 reviews

Bourbon Crossing II

The exterior of a brick home is shown, featuring a welcoming front door in a light teal shade. Surrounding landscaping includes neatly trimmed shrubs and flowering plants, with a concrete pathway leading to the entrance. A well-maintained lawn stretches out in front.

4.99 out of 5 average rating, 97 reviews

Backyard Bourbon Retreat

4.98 out of 5 average rating, 41 reviews

The exterior of the property showcases a spacious backyard with well-maintained grass, an outdoor fire pit surrounded by seating, and a hot tub visible beneath the deck. Soft lighting provides illumination as the sky transitions into dusk, highlighting the inviting atmosphere of the outdoor space.

Home in Versailles

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

A wooden shelf displays six barrels, each marked with labels and handwritten notes, reflecting a bourbon-tasting theme. Bar stools are positioned in front of the shelf, providing seating for guests in a welcoming space.

5 out of 5 average rating, 99 reviews

Van Winkle's Secret/Speakeasy (Hidden Room)

A rustic living room features a large leather sofa and a matching loveseat, complemented by a cozy armchair. A wooden coffee table sits centrally on a patterned rug, while framed artwork depicting bourbon barrels and glasses adorns the walls. Natural light fills the space through large windows.

4.98 out of 5 average rating, 60 reviews

Stave 32 “Bourbon Trail Retreat”

A spacious great room features a large sectional sofa with soft cushions and a coffee table placed on a vibrant area rug. A wall-mounted smart TV displays a selection of apps, while a modern kitchen with bar seating is visible in the background. Ambient lighting adds warmth.

5 out of 5 average rating, 87 reviews

Bourbon Central Waterfront Luxe near Buffalo Trace

An outdoor seating area features plush, wicker couches and a wooden coffee table, situated under a covered deck. A hot tub bubbles nearby, with peaceful lake views in the background. String lights create a soft illumination, enhancing the inviting atmosphere of the space.

4.91 out of 5 average rating, 54 reviews

Lakefront. Boat Dock. Private Bar. Hot Tub

Private house rentals

4.89 out of 5 average rating, 9 reviews

Bourbon Trail Getaway - 3 miles Buffalo Trace

A cozy living area features a grey sofa adorned with decorative pillows, accompanied by a patterned armchair. A round floral area rug sits on polished wooden flooring, while an open kitchen area with wooden cabinetry and modern appliances is visible in the background.

4.97 out of 5 average rating, 39 reviews

Bourbon Trail Hideaway

A charming stone home is surrounded by lush greenery and vibrant flowering shrubs. A stone pathway leads to the front door, framed by a variety of trees that provide shade and tranquility. Sunlight filters through the leaves, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 20 reviews

Bourbon Trail-Hot tub-Riverview-2.5miles BuffaloTr

4.86 out of 5 average rating, 59 reviews

Kentucky Bluegrass Retreat - Large Deck - lvl 2 EV

5 out of 5 average rating, 62 reviews

A circular seating area features six Adirondack chairs arranged around a stone fire pit. The surrounding grassy space is dotted with trees, with a vibrant sunset illuminating the sky in the background.

Home in Finchville

Country Retreat on Bourbon Trail - Fire Pit - King

4.99 out of 5 average rating, 84 reviews

Bennett House 4 full baths/5 bedrooms/private

A charming bungalow exterior is highlighted by vibrant green siding and white accents. A covered porch with intricate railing invites guests, while a pathway leads through well-maintained landscaping adorned with flowers and fresh grass. The setting sun casts a warm glow over the home.

4.96 out of 5 average rating, 96 reviews

River Row Bungalow

A modern farmhouse is depicted, showcasing a wraparound porch with rocking chairs. Lush greenery surrounds the property, which rests on a spacious lawn. The sky displays a gradient of vibrant colors during sunset, enhancing the peaceful setting.