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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Kentucky

  5.  Lexington
  6.  Lovers Leap Vineyards and Winery

Refine your search

Price per night

Amenity Filter

Rating

30 Best Family Vacation Rentals in Lovers Leap Vineyards and Winery (Starting from $168)

#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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
Bourbon Barrel Cottages #5 on Ky Bourbon Trail
Bourbon Barrel Cottages #5 on Ky Bourbon Trail
House
Lawrenceburg, KY, USA
2.4k from Lovers Leap Vineyards and Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$309
Average price / night
Check Availability
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
Check Availability
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
Check Availability
Restful Bourbon Trail Lodge with Pool and Hot Tub
Restful Bourbon Trail Lodge with Pool and Hot Tub
House
Lawrenceburg, KY, 40342, United States
5.6k from Lovers Leap Vineyards and Winery center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

28 reviews

$412
Average price / night
Check Availability
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
Check Availability
Award-winning 3 king bedroom retreat in historic downtown Lawrenceburg, steps from Main Street and minutes to the Kentucky Bourbon Trail.
Award-winning 3 king bedroom retreat in historic downtown Lawrenceburg, steps from Main Street and minutes to the Kentucky Bourbon Trail.
House
Lawrenceburg, KY, 40342, United States
5.7k from Lovers Leap Vineyards and Winery center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$337
Average price / night
Check Availability
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
Check Availability
Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi
Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi
House
Frankfort, KY, 40601, United States
5.7k from Lovers Leap Vineyards and Winery center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$393
Average price / night
Check Availability
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
Check Availability
Luxury 6BR Bourbon Farmhouse w/ Spa & SpeakEasy
Luxury 6BR Bourbon Farmhouse w/ Spa & SpeakEasy
House
Lawrenceburg, KY, 40342, United States
6.1k from Lovers Leap Vineyards and Winery center

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

6 Bedrooms14 Guests
10.0

Exceptional

75 reviews

$1062
Average price / night
Check Availability
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
Check Availability
Bourbon Trail/8 mins to distilleries/Fenced Yard/Pet-Friendly/Entire House
Bourbon Trail/8 mins to distilleries/Fenced Yard/Pet-Friendly/Entire House
House
Lawrenceburg, KY, 40342, United States
6.2k from Lovers Leap Vineyards and Winery center

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

3 Bedrooms6 Guests
9.8

Exceptional

45 reviews

$246
Average price / night
Check Availability
1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!
1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!
House
Lawrenceburg, KY, 40342, United States
6.3k from Lovers Leap Vineyards and Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

91 reviews

$463
Average price / night
Check Availability
Limestone Landing - Cozy Luxury Retreat w/ Hot Tub
Limestone Landing - Cozy Luxury Retreat w/ Hot Tub
House
Frankfort, KY, 40601, United States
6.8k from Lovers Leap Vineyards and Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

61 reviews

$237
Average price / night
Check Availability
Greenwood Farm log cabin close to the Bourbon Trail and Keeneland
Greenwood Farm log cabin close to the Bourbon Trail and Keeneland
Cabin
Versailles, KY, 40383, United States
7.0k from Lovers Leap Vineyards and Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

33 reviews

$466
Average price / night
Check Availability
Original Circa 1818 Oak Lodge
Original Circa 1818 Oak Lodge
Cabin
Lawrenceburg, KY, 40342, United States
8.3k from Lovers Leap Vineyards and Winery center

AC, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space

1 Bedroom5 Guests
9.4

Superb

53 reviews

$282
Average price / night
Check Availability
7 min to Wild Turkey and Four Roses - Sleeps 10 - Patio with Grill and View
7 min to Wild Turkey and Four Roses - Sleeps 10 - Patio with Grill and View
House
Lawrenceburg, KY, 40342, United States
8.5k from Lovers Leap Vineyards and Winery center

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

4 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$550
Average price / night
Check Availability
The Stagg House on the Ky River
The Stagg House on the Ky River
House
Frankfort, KY, 40601, United States
8.7k from Lovers Leap Vineyards and Winery center

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

2 Bedrooms7 Guests
9.8

Exceptional

19 reviews

$287
Average price / night
Check Availability
Encounter the Bluegrass & relax comfortably
Encounter the Bluegrass & relax comfortably
House
Frankfort, KY, 40601, United States
9.3k from Lovers Leap Vineyards and Winery center

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

3 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$363
Average price / night
Check Availability

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 Family Vacation Rentals in Lovers Leap Vineyards and Winery.

Lovers Leap Vineyards and Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 30 verified family-friendly vacation rentals in Lovers Leap Vineyards and Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Lovers Leap Vineyards and Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $168 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Lovers Leap Vineyards and Winery offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Lovers Leap Vineyards and Winery are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Lovers Leap Vineyards and Winery often include amenities such as Child Friendly, Wellness Facilities, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.