Vacation Rentals in Lovers Leap Vineyards and Winery, KY: Compare 10+ Sites & Save

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  6.  Lovers Leap Vineyards and Winery

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73 Best Vacation Rentals in Lovers Leap Vineyards and Winery (Starting from $165)

#4 Kentucky Bourbon Trail Bourbon Barrel Cottages
#4 Kentucky Bourbon Trail Bourbon Barrel Cottages
Ski Chalet
Lawrenceburg, KY, USA
2.3k from Lovers Leap Vineyards and Winery center

View, Parking, Security/Safety, Air Conditioner, Internet, Pet Friendly, Barbecue/Outdoor Cooking

2 Bedrooms4 Guests
9.9

Exceptional

8 reviews

$309
Average price / night
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Luxe Bourbon Trail Cabin– Hot Tub/Pickleball/Fire Pit/Pool/Game Room
Luxe Bourbon Trail Cabin– Hot Tub/Pickleball/Fire Pit/Pool/Game Room
Cabin
Lawrenceburg, KY, 40342, United States
0.5k from Lovers Leap Vineyards and Winery center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms12 Guests
9.8

Exceptional

11 reviews

$887
Average price / night
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Bourbon Barrel Cottages #2 of 5 on Kentucky trail
Bourbon Barrel Cottages #2 of 5 on Kentucky trail
Ski Chalet
Lawrenceburg, KY, USA
2.3k from Lovers Leap Vineyards and Winery center

Fireplace/Heating, Wellness Facilities, Parking, Security/Safety, Sports/Activities, Air Conditioner, Internet

2 Bedrooms4 Guests
9.8

Exceptional

43 reviews

$278
Average price / night
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Bourbon Trail Cabin-Sleeps 10-Hot Tub, Firepit by Iconiq Stays
Bourbon Trail Cabin-Sleeps 10-Hot Tub, Firepit by Iconiq Stays
House
LAWRENCEBURG, KY, 40342, United States
1.7k from Lovers Leap Vineyards and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

18 reviews

$600
Average price / night
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Bourbon Barrel Cottages #1 of 5 on Kentucky trail
Bourbon Barrel Cottages #1 of 5 on Kentucky trail
Ski Chalet
Lawrenceburg, KY, USA
2.3k from Lovers Leap Vineyards and Winery center

View, Fireplace/Heating, Wellness Facilities, Balcony/Terrace, Parking, Security/Safety, Air Conditioner

2 Bedrooms4 Guests
9.9

Exceptional

15 reviews

$309
Average price / night
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Bourbon Trail Cabin on the Farm
Bourbon Trail Cabin on the Farm
Cabin
Lawrenceburg, KY, 40342, United States
2.3k from Lovers Leap Vineyards and Winery center

AC, Balcony, Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

10.0

Exceptional

52 reviews

$199
Average price / night
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Bourbon Barrel Cottages #3 on Ky Bourbon Trail
Bourbon Barrel Cottages #3 on Ky Bourbon Trail
House
Lawrenceburg, KY, USA
2.4k from Lovers Leap Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$361
Average price / night
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Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Cottage
Lawrenceburg, KY, 40342, United States
2.3k from Lovers Leap Vineyards and Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

14 reviews

$388
Average price / night
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Bourbon Barrel Cottages #4 on Ky. Bourbon Trail
Bourbon Barrel Cottages #4 on Ky. Bourbon Trail
House
Lawrenceburg, KY, 40342, United States
2.3k from Lovers Leap Vineyards and Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$381
Average price / night
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Twin Cottages Presale Cottage 7
Twin Cottages Presale Cottage 7
House
Lawrenceburg, KY, USA
2.4k from Lovers Leap Vineyards and Winery center

Accommodations, Country houses, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$429
Average price / night
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Home in Frankfort countryside-close to distilleries, Keeneland &Churchill Downs!
Home in Frankfort countryside-close to distilleries, Keeneland &Churchill Downs!
House
Frankfort, KY, 40601, United States
2.4k from Lovers Leap Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$479
Average price / night
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Twin Cottages Presale Bourbon Barrel Cottages 6
Twin Cottages Presale Bourbon Barrel Cottages 6
House
Lawrenceburg, KY, USA
2.4k from Lovers Leap Vineyards and Winery center

Accommodations, Country houses, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

2 Bedrooms4 Guests
New to Booking
$466
Average price / night
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Bourbon Barrel Cottages #6 Kentucky Bourbon Trail Hot Tub and Fire Pit
Bourbon Barrel Cottages #6 Kentucky Bourbon Trail Hot Tub and Fire Pit
Apartment
Lawrenceburg, KY, 40342, United States
2.4k from Lovers Leap Vineyards and Winery center

AC, Barbecue, Breakfast Available, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$468
Average price / night
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Bourbon Barrel Cottages Main House
Bourbon Barrel Cottages Main House
House
Lawrenceburg, KY, USA
2.6k from Lovers Leap Vineyards and Winery center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis

6 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$1150
Average price / night
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Bourbon Barrel Cottages #7 on Kentucky's Bourbon Trail with Hot Tub and Firepit
Bourbon Barrel Cottages #7 on Kentucky's Bourbon Trail with Hot Tub and Firepit
Cottage
Lawrenceburg, KY, 40342, United States
2.4k from Lovers Leap Vineyards and Winery center

AC, Breakfast Available, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$515
Average price / night
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Historic Downtown Spot - On The Bourbon Trail
Historic Downtown Spot - On The Bourbon Trail
House
Lawrenceburg, KY, USA
5.7k from Lovers Leap Vineyards and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom6 Guests
9.3

Superb

3 reviews

$266
Average price / night
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Bourbon Barrel Cottages # 1 on Bourbon Trail HOT TUB close to all distilleries
Bourbon Barrel Cottages # 1 on Bourbon Trail HOT TUB close to all distilleries
Cabin
Lawrenceburg, KY, 40342, United States
2.4k from Lovers Leap Vineyards and Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

26 reviews

$377
Average price / night
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Whiskey Woods
Whiskey Woods
House
Frankfort, KY, USA
7.3k from Lovers Leap Vineyards and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$279
Average price / night
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Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Cottage
Lawrenceburg, KY, 40342, United States
2.4k from Lovers Leap Vineyards and Winery center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

12 reviews

$381
Average price / night
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The Kentucky Bluegrass Retreat
The Kentucky Bluegrass Retreat
House
Frankfort, KY, USA
9.0k from Lovers Leap Vineyards and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

3 Bedrooms6 Guests
9.2

Superb

13 reviews

$168
Average price / night
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Close to ALL main distilleries Bourbon Trl HOT TUB
Close to ALL main distilleries Bourbon Trl HOT TUB
House
Lawrenceburg, KY, 40342, United States
2.6k from Lovers Leap Vineyards and Winery center

AC, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

6 Bedrooms16 Guests
New to Booking
$1639
Average price / night
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Riverside Roost -bourbon themed waterfront home
Riverside Roost -bourbon themed waterfront home
House
Versailles, KY, 40383, United States
3.4k from Lovers Leap Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$253
Average price / night
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Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Cottage
Frankfort, KY, 40601, United States
3.9k from Lovers Leap Vineyards and Winery center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
9.8

Exceptional

41 reviews

$198
Average price / night
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The Green Cabin-on-The Bourbon Trail-    High Proof Since 2018! Recent Upgrades.
The Green Cabin-on-The Bourbon Trail- High Proof Since 2018! Recent Upgrades.
Cabin
Lawrenceburg, KY, 40342, United States
4.1k from Lovers Leap Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

226 reviews

$222
Average price / night
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Lux Estate-Poker Room-Hot Tub-near Bourbon Trail
Lux Estate-Poker Room-Hot Tub-near Bourbon Trail
House
Lawrenceburg, KY, 40342, United States
4.2k from Lovers Leap Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater

6 Bedrooms16 Guests
10.0

Exceptional

6 reviews

$881
Average price / night
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The Gathering at Old Frankfort
The Gathering at Old Frankfort
House
Lawrenceburg, KY, 40342, United States
4.2k from Lovers Leap Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

7 Bedrooms20 Guests
10.0

Exceptional

4 reviews

$1499
Average price / night
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Bourbon Trail , Cheerful 2 bedroom home
Bourbon Trail , Cheerful 2 bedroom home
House
Lawrenceburg, KY, 40342, United States
4.5k from Lovers Leap Vineyards and Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms4 Guests
9.6

Exceptional

27 reviews

$165
Average price / night
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Other accommodation types in Lovers Leap Vineyards and Winery:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Lovers Leap Vineyards and Winery.

Lovers Leap Vineyards and Winery Vacation Rentals on the Map

Frequently Asked Questions

You can explore 73 verified vacation rentals in Lovers Leap Vineyards and Winery. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Lovers Leap Vineyards and Winery vary depending on the season, property size, and location. Rates typically start from around $165 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Lovers Leap Vineyards and Winery include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Lovers Leap Vineyards and Winery welcome pets. Currently, 36 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Lovers Leap Vineyards and Winery often include amenities such as Fireplace/Heating, Wellness Facilities, and Barbecue/Outdoor Cooking. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.