Places to stay near Lovers Leap Vineyards and Winer

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Top-rated vacation rentals near Lovers Leap Vineyards and Winer

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Top guest favorite
The cabin exterior is nestled within a wooded landscape, showcasing a wooden facade. A welcoming porch is framed by two Adirondack chairs, with stepping stones leading toward the entrance. Twinkling lights hang across the trees, enhancing the tranquil evening ambiance.
Cabin in Lawrenceburg
4.99 out of 5 average rating, 193 reviews

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Top guest favorite
Cabin in Frankfort
5 out of 5 average rating, 115 reviews

Bourbon Trail log Cabin! Hot tub~hiking~game shed!

🌲FOR CHRISTMAS- home is transformed into cozy holiday cabin retreat! A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plenty of fun on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

Top guest favorite
A cozy bedroom features a full-sized bed draped in a patterned blue and white coverlet. A bedside lamp and a small table with decorative items complement the space. Natural light filters through a small window, creating a serene ambiance.
Apartment in Wilmore
4.97 out of 5 average rating, 346 reviews

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

Top guest favorite
A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.
Farm stay in Frankfort
4.99 out of 5 average rating, 139 reviews

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

Top guest favorite
The living area showcases a light-colored sofa with decorative pillows, positioned on a patterned rug. A coffee table with a vibrant design complements the space, while artwork adorns the walls. An open dining area features a round table surrounded by white chairs, enhancing the bright, airy atmosphere.
Apartment in Versailles
4.98 out of 5 average rating, 354 reviews

High style on the Bourbon Trail

Historic 1 bedroom apt in the heart of horse country & the bourbon trail. Quiet bedroom. Central Main St. location in charming Versailles, steps from local coffee shop & bourbon bar. Walk to food, shopping and park. Light filled apartment with vaulted ceiling and exposed brick wall. Cozy bedroom has memory foam Cal king bed and percale cotton sheets. The decor is an eclectic mix of antiques, Ferrick Mason textiles, wallpapers and Alex K Mason original art. Parking space. Free washer & dryer.

Top guest favorite
Lush green grass frames the scene, with two flowering trees prominently in the foreground. A wooden fence lines the area, leading to a cottage that is partially obscured by the trees. Natural light brightens the surroundings on a clear day.
Guesthouse in Nicholasville
4.98 out of 5 average rating, 369 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Guest favorite
The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.
Cabin in Louisville
4.98 out of 5 average rating, 249 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite
A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.
Train in Lawrenceburg
4.99 out of 5 average rating, 467 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Top guest favorite
A well-equipped kitchen features a spacious wood island with two upholstered stools. Modern appliances, including a gas range and sleek cabinetry, complement the space. Natural light streams through the windows, enhancing the inviting atmosphere, while tasteful decor adds a touch of character.
Loft in Frankfort
4.98 out of 5 average rating, 197 reviews

The Loft - Cozy Retreat in Historic Downtown

Experience the warmth and charm of The Loft your top-rated fall retreat just 8 minutes from downtown. Stroll to the Capitol, see the autumn sights, and take in Horse Country nearby. Snuggle into a cozy bed, curl up on the couch, and enjoy modern touches in your private second-floor hideaway. With parking at the door and a hygge-inspired vibe, it’s perfect for crisp days and cozy nights. Just minutes from 13 distilleries, The Loft is your ideal base for a stylish Bourbon Trail escape.

Top guest favorite
A large window allows natural light to brighten the entrance area, showcasing a view of the street and nearby shops. A modern light fixture hangs from the ceiling, complementing the open and airy feel of the space.
Apartment in Frankfort
4.97 out of 5 average rating, 218 reviews

Bing’s Downtown Guest Suite on Main

Make your home away from home at this centrally-located guest suite encompassing the entire second floor of the historic Bing’s Building in the center of downtown Frankfort, Kentucky! Historic downtown guest suite with modern amenities located in the heart of the capital city. Within blocks of great dining, shopping, entertainment, and historic sites. A short distance to Buffalo Trace and other popular distilleries, Keeneland racetrack, bluegrass horse country and much more!

Superhost
A private heated salt-water pool is surrounded by a spacious concrete deck, featuring two black lounge chairs for relaxation. Lush green trees provide a natural backdrop, enhancing the tranquil outdoor space. The pool's clear blue water invites enjoyment and leisure.
Guesthouse in Lexington
4.88 out of 5 average rating, 304 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Top guest favorite
A well-maintained backyard area is highlighted by a green hammock suspended between trees. The brick apartment is elevated with a wooden deck and stairs leading to the entrance. Surrounding the space, manicured shrubs and grass create a peaceful outdoor environment.
Guesthouse in Frankfort
4.98 out of 5 average rating, 132 reviews

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Popular amenities for vacation rentals near Lovers Leap Vineyards and Winer

  1. Airbnb
  2. United States
  3. Kentucky
  4. Anderson County
  5. Lawrenceburg
  6. Lovers Leap Vineyards and Winer