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House vacation rentals in Herrington Lake

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Top-rated house rentals in Herrington Lake

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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

4.95 out of 5 average rating, 356 reviews

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.

A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.

Home in Lexington

4.93 out of 5 average rating, 777 reviews

Restored charm! Walk to Rupp. Easy Keeneland drive

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert or sporting event at nearby Rupp Arena (5 minute walk), watch the horse races at Keeneland (10 minute drive down the road), tour the bourbon distillery right around the corner, or explore the unique offerings of downtown Lexington. Stay in the heart of it all!

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

Nestled on the Kentucky River in Frankfort, KY, our peaceful retreat is surrounded by historic chestnut trees and wildlife like deer & cardinals. Just 5 miles from Buffalo Trace, 6.7 miles from Castle & Key, and 10 miles from Woodford Reserve and Whiskey Thief, it’s ideal for bourbon enthusiasts. Enjoy the river beach, backyard BBQs in summer, or cozy nights by the fireplace in winter—wood provided. Fully stocked kitchen, pet and family-friendly, with a secluded vibe yet close to the main road.

A modern kitchen features light-colored cabinetry and a granite countertop, equipped with stainless steel appliances. A window with soft yellow curtains allows natural light to brighten the space. Decorative tile backsplashes add a subtle touch, while a rug enhances the floor area.

Home in Lexington

4.92 out of 5 average rating, 588 reviews

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

Top guest favorite

The cottage exterior features a welcoming front porch with wooden rocking chairs and a swing. Colorful artwork adorns the walls, complemented by a garden of flowers. The door is a vibrant blue, and tall trees provide shade overhead, creating a peaceful entrance.

4.93 out of 5 average rating, 738 reviews

Berea Painter's Cottage

Eclectic, clean, comfortable cottage featuring original artwork, located in walking distance of Berea College Campus, Artisan Village/Old Town area, Art Galleries, Unique Shops, The Lot, Rebel Rebel, Nightjar, Sunhouse Craft, and Native Bagel. A short drive to the Pinnacles and Kayaking at Owsley Fork Lake. The location is great. A cozy patio in front of the home with a swing and a tree canopied deck in back that feels like being in a treehouse. Basic TV channels and high-speed internet.

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

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

A large, in-ground pool reflects the surroundings, framed by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a spacious deck attached to the house. The inviting outdoor space is ideal for relaxation and enjoyment.

Home in Lexington

4.87 out of 5 average rating, 115 reviews

4 BR 3 Bath 9 beds! Hot Tub, Pool, Movie room!

Welcome to The Komi. This 4 bed, 3 bath home is an oasis in the middle of Lexington. This cozy getaway has SO much to offer; in ground pool, hot tub, stone fire pit, basketball court, and thats just the outside! Inside boasts an open floor plan living area with a HUGE dining table. Three bedrooms upstairs along with two baths. Downstairs is the perfect place for the kids with bunk bed trundles that sleeps up to 8. Oh, and did I mention the home movie theater! The Komi has it all!

A serene outdoor area is highlighted by a covered patio featuring comfortable seating and a hot tub. Ambient lighting creates a cozy atmosphere, while lush green grass and carefully placed shrubs enhance the inviting outdoor space.

Home in Georgetown

4.97 out of 5 average rating, 152 reviews

The Luxe/Hot Tub/12min to Horse Park/30 Min to Ark

Where elegant vintage meets modern design. Come and enjoy this historic home on a quiet street in downtown Georgetown. You will be within walking distance of shops, restaurants, Georgetown College, and parks. Home is also a ten minute commute to the Kentucky Horse Park and interstate. Equipped with a fully stocked kitchen, full dining room, and a Loft office space. You can enjoy your Private backyard oasis boasting a relaxing hot tub, fire pit, black stone grill, and outdoor tv.

Top guest favorite

The entrance of the cottage features a wooden door framed by two windows, offering natural light. A decorative wreath adorns the door, and wall sconces provide additional illumination. The exterior showcases white siding with teal accents, complemented by a brick pathway leading to the door.

Home in Winchester

4.91 out of 5 average rating, 813 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Top guest favorite

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

4.97 out of 5 average rating, 116 reviews

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

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, a sporting event, or just looking for a fun getaway, we have all the entertainment you need! Featuring a pool, hot tub, arcade machine, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!

The cottage's exterior features a charming red facade with a steep roof, framed by lush greenery. A pathway leads to the welcoming front door, flanked by two tall shrubs. The landscaped garden includes various plants and decorative stones, creating an inviting entrance.

Home in Harrodsburg

4.93 out of 5 average rating, 142 reviews

The Betsy Sweat Cottage.

****This home is all Electric . Carbon Monoxide detector located beside bed .This is a Small Home..The plant collection will provide you with natural oxygen and new split heating and cooling will clean the air providing you with a restful sleep (day or nite) Close to Danville 9.5 miles (15 minutes away). , Frankfort 32 miles (40 minutes away) Lexington ****FYI- There is an additional charge of $30 extra charge for more than 2 guest.. children no extra charge.

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

Limestone Landing is a modern, fully renovated, open space home in a country neighborhood setting. The home is the perfect retreat for your next getaway to Kentucky. Conveniently situated only a 1/4 mile from Castle and Key Distillery and 2 miles from Woodford Reserve. 1/2 mile from the highly rated restaurant and bourbon bar, The Stave. Indulge in the ultimate bourbon tasting experience, knowing that comfort awaits you at your cozy haven.

Vacation rentals for every style

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Popular amenities for Herrington Lake house rentals

Free parking on premises

Air conditioning

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

A sparkling pool is surrounded by a stone patio and six lounge chairs, inviting relaxation. Umbrella shade provides a resting area, while string lights illuminate the scene as dusk sets in. Lush trees add a natural backdrop, enhancing the tranquil outdoor atmosphere.

Home in Shelbyville

4.97 out of 5 average rating, 30 reviews

Pool is Open! + Hot Tub, 10 min to Bulleit

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

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

An aerial view captures a spacious property surrounded by lush greenery. A large pool is situated in the backyard, with a fenced area visible. The home, featuring a combination of roof styles, is nestled in a semi-rural setting with nearby residential structures.

Home in Shelbyville

4.76 out of 5 average rating, 59 reviews

Pool*HOT TUB*Bourbon Trail

Top guest favorite

A spacious, single-story house features a clean white exterior with dark roofing and large arched windows. Manicured grass surrounds a central pathway that leads to the front door, framed by evenly spaced shrubs. A clear blue sky adds to the welcoming atmosphere.

5 out of 5 average rating, 31 reviews

Private Estate on Bourbon Trail w/ Beautiful Pool

Home in Richmond

5 out of 5 average rating, 11 reviews

Heart of Richmond

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

Weekly 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.

5 out of 5 average rating, 37 reviews

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

Top guest favorite

A modern farmhouse exterior is showcased, featuring a light grey façade with stone accents. A spacious driveway leads to a two-car garage on the right. Lush green grass surrounds the home, complemented by a clear blue sky and wispy clouds overhead.

Home in Lancaster

5 out of 5 average rating, 35 reviews

Home on the Dix River with Movie Theater & Hot Tub

An airy kitchen is presented with a marble countertop, showcasing a modern sink and stylish faucet. In the background, large windows allow natural light to fill the open living space, revealing a cozy seating area with a fireplace and lake view.

Home in Lancaster

4.83 out of 5 average rating, 60 reviews

Lakefront property - Higher Ground

A serene view of a cove on Herrington Lake is captured, showcasing a covered dock gently resting on calm water. A lush, tree-lined hill rises in the background, with a path leading upwards. Morning mist softly hovers over the water, adding to the peaceful atmosphere.

Home in Harrodsburg

5 out of 5 average rating, 18 reviews

Tranquility Cove: 5-Bedroom on Herrington Lake

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.

Home in Lawrenceburg

4.95 out of 5 average rating, 61 reviews

Bourbon Crossing II

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

A living area features two textured armchairs and a gray sofa, positioned near a wooden coffee table. A patterned rug lies beneath, complementing the space. Natural light floods in through multiple windows, while a dining table is visible in the background with wooden chairs.

Home in Danville

4.86 out of 5 average rating, 21 reviews

Fore the Lake

Top guest favorite

A spacious fire pit area features comfortable Adirondack chairs arranged around a stone fire pit, surrounded by a gravel patio. String lights overhead create a warm atmosphere against the backdrop of rolling hills and a sunset sky.

5 out of 5 average rating, 87 reviews

LUX | HotTub | Firepit | Man Cave | On BRBN Trail!

Private house rentals

Top guest favorite

A new six-seater hot tub is showcased, illuminated by soft blue lights. A small platter rests on the edge, accompanied by two wine glasses. In the background, warm light spills from an inviting seating area visible through the glass doors.

Home in Frankfort

4.97 out of 5 average rating, 36 reviews

Hot Tub > 3 King Beds > 7 mins to Buffalo Trace

The charming exterior of the Bluegrass & Bourbon Bungalow features a welcoming porch with white railing and hanging plants. A well-maintained stone pathway leads to the entrance, framed by landscaped grass and flower beds. The light-colored house is surrounded by mature trees, offering a peaceful setting.

Home in Harrodsburg

4.97 out of 5 average rating, 29 reviews

Elegant Retreat | Hot Tub, 3 Kings, Bourbon Trail

Top guest favorite

The entrance features a pair of elegantly crafted wooden doors with intricate glass designs, set against a stone facade. Flanking the doors are potted flowers and rustic elements, such as a barrel and a vintage container, enhancing the welcoming ambiance.

Home in Harrodsburg

5 out of 5 average rating, 22 reviews

Braxton Manor at Creekside Retreat

Top guest favorite

A two-story home is surrounded by trees, featuring a spacious deck and an outdoor gathering area. The fire pit is surrounded by multiple seating arrangements, all set on gravel. String lights add a touch of warmth to the outdoor space, creating an inviting atmosphere.

Home in Lawrenceburg

5 out of 5 average rating, 22 reviews

Hot Tub, Sauna & Games at Bourbon Trail Escape!

Top guest favorite

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

5 out of 5 average rating, 29 reviews

The Back 40 ~ Modern*Bourbon*Scenic*Private

Top guest favorite

A modern one-story home is showcased, featuring a dark exterior with contrasting wooden porch posts. Blue outdoor chairs are arranged invitingly on the covered porch. A spacious driveway leads to an oversized garage, with a lawn area visible in the background.

5 out of 5 average rating, 28 reviews

New Quiet Retreat Hot Tub Shaker Village Danville

Top guest favorite

A cozy backyard scene is illuminated by string lights above a fire pit surrounded by four comfortable chairs. In the background, a hammock is seen hanging between two trees, adding to the inviting outdoor space. A privacy fence provides a sense of seclusion.

Home in Springfield

5 out of 5 average rating, 43 reviews

Best Bourbon Location, Private Hottub, Walk & Eat

Top guest favorite

A welcoming living space includes a smooth wooden floor and light-colored walls. A comfortable seating area features two patterned armchairs and a modern coffee table, with a flat-screen TV mounted on the wall. Bar stools are lined up at a counter, connecting to the kitchen area.

Home in Harrodsburg

4.98 out of 5 average rating, 44 reviews

The Farmhouse at Pleasant Hill

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