Rolling Hills holiday homes

We found 1,090 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Rolling Hills that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Rolling Hills

Showing deals for:4 Dec - 11 Dec

Private kitchen
Exterior
Living area
Terrace/patio
Exceptional
(11 reviews)

Castle St Matthews

Louisville

8% off
NZ$15,476
for 7 nights, 1 home
NZ$2,211 per night
includes taxes & fees
Castle St Matthews
As you open the door, this is the view you will be walking into.
To make it even more special for you, we have a 6 people private hottub with lovely views of the Ohio river!
Kentucky Kingdom and Hurricane Bay Water Park is a MUST-SEE for families! It has fun-filled rides and activities for ALL ages! Get ready for all the splashing good memories that will last your family a lifetime!
Guests Fav #1: Spacious, comfy and luxurious bedrooms
Exceptional
(28 reviews)

Luxe Waterfront Newspaper Featured w/ Fire Pit Cinema Hot Tub Sauna Pets Views

Jeffersonville

7% off
NZ$9,327
for 7 nights, 1 home
NZ$1,332 per night
includes taxes & fees
Luxe Waterfront Newspaper Featured w/ Fire Pit Cinema Hot Tub Sauna Pets Views
Family room off of foyer and next to Living room area 1 with queen bed And bunks
Exterior
Terrace/patio
Foyer as you walk in front door
Exceptional
(14 reviews)

Beautiful views and sunrises overlooking the water. Spacious home with elevator.

Jeffersonville

19% off
NZ$6,663
for 7 nights, 1 home
NZ$952 per night
includes taxes & fees
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Private kitchen
Living area
Enjoy the sunrise over the river from the enclosed sunroom
Living area
Exceptional
(29 reviews)

Fully Remodeled Exquisite Louisville Area Tranquil Riverfront Home!

Jeffersonville

8% off
NZ$5,714
for 7 nights, 1 home
NZ$816 per night
includes taxes & fees
Fully Remodeled Exquisite Louisville Area Tranquil Riverfront Home!
Outdoor dining
Dining
Room
Private kitchen
Wonderful
(17 reviews)

River City Retreat

Jeffersonville

7% off
NZ$3,172
for 7 nights, 1 home
NZ$453 per night
includes taxes & fees
River City Retreat
Living area
Pool
Exterior
Property grounds
Exceptional
(11 reviews)

Safe, scenic, and convenient. Bordering a State Park!

Louisville

13% off
NZ$6,771
for 7 nights, 1 home
NZ$967 per night
includes taxes & fees
Safe, scenic, and convenient. Bordering a State Park!
Terrace/patio
Exterior
Living area
Interior
Exceptional
(87 reviews)

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Louisville

7% off
NZ$12,868
for 7 nights, 1 home
NZ$1,838 per night
includes taxes & fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
1st floor sunroom TV
Living area
Living area
Living area
Excellent
(10 reviews)

Lovely Gem in the Vibrant Highlands close to it all!

Louisville

7% off
NZ$11,470
for 7 nights, 1 home
NZ$1,639 per night
includes taxes & fees
Lovely Gem in the Vibrant Highlands close to it all!
Catwalk adjoins the upstairs bedrooms.
Living Room, Breakfast area. Kitchen is to the right.
Front of the home.
Friendly front porch.
Exceptional
(57 reviews)

Near Highways and a 20 Min Drive to Louisville's Main Attractions

Louisville

7% off
NZ$4,862
for 7 nights, 1 home
NZ$695 per night
includes taxes & fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Terrace/patio
Interior
Exterior
Interior
Exceptional
(27 reviews)

Historic Mansion-Modern Amenities, Sauna, Fire Pit, Hot Tub, Deck, Walk to Dine

Louisville

8% off
NZ$12,198
for 7 nights, 1 home
NZ$1,743 per night
includes taxes & fees
Historic Mansion-Modern Amenities, Sauna, Fire Pit, Hot Tub, Deck, Walk to Dine
Interior
Living area
Exterior detail
Private kitchen
Exceptional
(131 reviews)

The Cozy Bungalow-Historic Highlands-Bardstown Rd

Louisville

7% off
NZ$5,301
for 7 nights, 1 home
NZ$757 per night
includes taxes & fees
The Cozy Bungalow-Historic Highlands-Bardstown Rd
Interior
Exterior
Room
Lobby
Exceptional
(147 reviews)

Ultimate Getaway: Expansive Home with Hot Tub & Relaxation

Louisville

7% off
NZ$8,619
for 7 nights, 1 home
NZ$1,231 per night
includes taxes & fees
Ultimate Getaway: Expansive Home with Hot Tub & Relaxation
Kitchen
Private kitchen
Pool
New separete entrance to a new addition
Exceptional
(24 reviews)

Spacious 5BR Getaway – Pool, Patios & Fun

Louisville

7% off
NZ$14,192
for 7 nights, 1 home
NZ$2,027 per night
includes taxes & fees
Spacious 5BR Getaway – Pool, Patios & Fun
Interior
Dining
Living area
Private kitchen
Excellent
(14 reviews)

Highlands Three Bedroom House - Walk to Restaurants and Bars!

Louisville

7% off
NZ$2,829
for 7 nights, 1 home
NZ$404 per night
includes taxes & fees
Highlands Three Bedroom House - Walk to Restaurants and Bars!
Creek on property
Front porch where you can have your gourmet breakfast and enjoy nature.
Private entrance from porch, beamed ceiling, antique furnishings.
Bathroom is adjacent to bedroom
Exceptional
(21 reviews)

Captain's Annex; close to Bourbon Trail and Churchill Downs, far from ordinary!

Louisville

8% off
NZ$1,994
for 7 nights, 1 home
NZ$285 per night
includes taxes & fees
Captain's Annex; close to Bourbon Trail and Churchill Downs, far from ordinary!
Relax in the brand new kitchen with everything you need to make a delicious meal
Interior
Property grounds
Living area
Exceptional
(127 reviews)

Charming Private Bungalow with EV Charger Near Downtown Louisville

Louisville

11% off
NZ$2,025
for 7 nights, 1 home
NZ$289 per night
includes taxes & fees
Charming Private Bungalow with EV Charger Near Downtown Louisville
Room
Front of house - just steps from "Restaurant Row" on Bardstown Road.
Living area
Living area
Exceptional
(172 reviews)

Elegant Home Steps to Restaurant Row!

Louisville

7% off
NZ$2,902
for 7 nights, 1 home
NZ$415 per night
includes taxes & fees
Elegant Home Steps to Restaurant Row!
Outdoor casual decking area
Living room w/pullout bed
Springtime in Louisville
Bedroom #2
Exceptional
(29 reviews)

Louisville GEM, newly furnished, super clean, in a safe trendy area

Louisville

10% off
NZ$1,906
for 7 nights, 1 apartment
NZ$272 per night
includes taxes & fees
Louisville GEM, newly furnished, super clean, in a safe trendy area
Room
Private kitchen
Living area
Living area
Exceptional
(37 reviews)

Charming Clifton Loft with Balcony & Free

Louisville

19% off
NZ$1,675
for 7 nights, 1 apartment
NZ$239 per night
includes taxes & fees
Charming Clifton Loft with Balcony & Free
Ideal for Bourbon Trail trips, bachelor parties, events
Cook with Ease in the Full Kitchen
Spacious Living Area with Tropical Charm
• Whiskey Row Luxury Rental
• Best Airbnb near Kentucky Convention Center
• Louisville Airbnb for bachelor party
• Bourbon trail group Airbnb Louisville
• Louisville downtown luxury group rental
Exceptional
(12 reviews)

Louisville 3BR | Walk to NuLu | Sleeps 8

Louisville

12% off
NZ$7,082
for 7 nights, 1 home
NZ$1,012 per night
includes taxes & fees
Louisville 3BR | Walk to NuLu | Sleeps 8
Room
Interior
Living area
Private kitchen
Exceptional
(39 reviews)

Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi

Louisville

15% off
NZ$1,643
for 7 nights, 1 home
NZ$235 per night
includes taxes & fees
Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
Private kitchen
Exterior
Interior
Dining
Exceptional
(6 reviews)

3-bedroom condo in Norton Commons

Prospect

8% off
NZ$4,365
for 7 nights, 1 apartment
NZ$624 per night
includes taxes & fees
3-bedroom condo in Norton Commons
Interior
Room
Games room
Private kitchen
Wonderful
(14 reviews)

Rooftop Patio & Games in Historic Highlands

Louisville

15% off
NZ$2,428
for 7 nights, 1 apartment
NZ$347 per night
includes taxes & fees
Rooftop Patio & Games in Historic Highlands
Private kitchen
Riverfront view
Room
Living area
Exceptional
(54 reviews)

Waterfront Apartment - Downstairs Unit

Jeffersonville

8% off
NZ$2,998
for 7 nights, 1 apartment
NZ$428 per night
includes taxes & fees
Waterfront Apartment - Downstairs Unit
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Rolling Hills getaway

Learn about the unique charm of Rolling Hills with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Rolling Hills

Are you looking for attractions to see in the area? Venture out of your cosy holiday rental and check out everything that makes Rolling Hills a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Valhalla Golf Club (6.4 mi / 10.3 km)
  • Louisville Zoo (8.7 mi / 14 km)
  • Kentucky Kingdom (10.9 mi / 17.6 km)
  • Churchill Downs (11.7 mi / 18.9 km)
  • Polo Fields Golf and Country Club (7.6 mi / 12.2 km)
  • Long Run Golf Course (8.3 mi / 13.3 km)

Exploring the natural landscape of Rolling Hills

Whether you're looking for fun outdoor activities or just want to take in the scenery, Rolling Hills is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • E.P. Tom Sawyer State Park (1.1 mi / 1.7 km)
  • Cherokee Park (7 mi / 11.2 km)
  • Beckley Creek Park (7.5 mi / 12.2 km)
  • Louisville Waterfront Park (7.8 mi / 12.5 km)
  • Louisville Mega Cavern (8.8 mi / 14.2 km)
  • Iroquois Park (14.1 mi / 22.8 km)

Transport options to and around Rolling Hills

The nearest airport is in Louisville, KY (LOU-Bowman Field), located 6.3 mi (10.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Louisville International Airport (SDF), which is 11.1 mi (17.8 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Rolling Hills?
Different things can determine how much you pay for a holiday home in Rolling Hills, like the type of property, season and length of stay. Still, all of our holiday homes have one thing in common — exceptional value. Simply add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Rolling Hills?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Rolling Hills travel dates to view your options on Bookabach. Did someone just say "private pool"? Use our filters to pick the features and amenities you want.
What are the top attractions for families in Rolling Hills?
Keep the kids amused at these awesome family-friendly attractions in Rolling Hills:
  • Louisville Mega Cavern
  • Louisville Zoo
  • Locust Grove Historic Home
How old do you have to be to rent a holiday home in Rolling Hills?
You should check with the Rolling Hills holiday home you're looking at on Bookabach as age restrictions vary. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Rolling Hills for?
It's down to the Rolling Hills property. To see all available options offering extended stays, simply type your dates and number of people into the Bookabach search page. Enjoy having the entire property to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a backyard where your little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

More holiday ideas