Default HTG hotel image

Rolling Hills Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rolling Hills holiday rentals

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

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (87 reviews)
"We had a great time! "
United States
Amber H.
The price is NZ$1,916
includes taxes & fees
16 Aug - 17 Aug
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

2. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
9.0 out of 10, Wonderful, (2 reviews)
"Was great enjoyed our stay and time there"
United States
Tammy
The price is NZ$215
includes taxes & fees
11 Sept - 12 Sept
StudioRes by Marriott Louisville East

3. Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods
Louisville
10.0 out of 10, Exceptional, (85 reviews)
"Home was great for a short stay. Kitchen fully furnished and all niceties such as coffee, snacks and toiletries. "
United States
Tony A.
The price is NZ$580
includes taxes & fees
17 Aug - 18 Aug
Charming house in one of Louisville's most coveted neighborhoods

4. St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"The neighborhood is safe and we walked around to enjoy all the nearby shops and restaurants. Very quiet and peaceful, enjoyed the porch every morning."
United States
Stacy B.
The price is NZ$553
includes taxes & fees
20 Aug - 21 Aug
St. Matthew’s - Walk to Shops & Restaurants

5. OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr

OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr
Hikes Point
10.0 out of 10, Exceptional, (67 reviews)
"Nice property close to attractions."
United States
Glenn C.
The price is NZ$776
includes taxes & fees
24 Aug - 25 Aug
OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr

6. The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Louisville
10.0 out of 10, Exceptional, (212 reviews)
"Beautiful views very relaxing great place to get away from everyday life! "
United States
Krista P.
The price is NZ$767
includes taxes & fees
9 Sept - 10 Sept
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

7. Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (132 reviews)
"It was a great stay the property was super clean and the property manager was great!"
United States
Cole T.
The price is NZ$395
includes taxes & fees
11 Sept - 12 Sept
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

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

Near Highways and a 20 Min Drive to Louisville's Main Attractions
Louisville
10.0 out of 10, Exceptional, (57 reviews)
"Ross was super helpful from start to finish, and had plenty of space for our 14 guests to stay. This property would be very very high on my list to stay at again as a home base for a future Kentucky Derby weekend, or even a bourbon trail trip."
United States
Stephen Y.
The price is NZ$701
includes taxes & fees
7 Sept - 8 Sept
Near Highways and a 20 Min Drive to Louisville's Main Attractions

9. +Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (95 reviews)
"6 of us met from 3 different stars to celebrate a birthday. The house was perfect, location couldn’t have been better & everyone had a great time!"
United States
Dawn D.
The price is NZ$574
includes taxes & fees
31 Aug - 1 Sept
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

10. Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (25 reviews)
"Everything was outstanding!"
United States
John W.
The price is NZ$478
includes taxes & fees
18 Aug - 19 Aug
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

11. Charming Clifton Loft with Balcony & Free

Charming Clifton Loft with Balcony & Free
Clifton
10.0 out of 10, Exceptional, (36 reviews)
"Everything was exactly as described. Location is perfect near great shops and restaurants. Will definitely use again. Owner super nice and great communicator. "
United States
Amanda H.
The price is NZ$296
includes taxes & fees
17 Aug - 18 Aug
Charming Clifton Loft with Balcony & Free

12. 6 King Beds | Hot Tub | Highlands Mansion

6 King Beds | Hot Tub | Highlands Mansion
Highlands Douglass
10.0 out of 10, Exceptional, (121 reviews)
"The house was clean and well equipped for our large group. Close to town and fun tourist things to do. Would definitely stay here again!"
United States
Melissa G.
The price is NZ$2,161
includes taxes & fees
17 Aug - 18 Aug
6 King Beds | Hot Tub | Highlands Mansion

13. Luxe Riverfront Newspaper Featured w/ Hot Tub Sauna Cinema Fire Pit Pets Views

Luxe Riverfront Newspaper Featured w/ Hot Tub Sauna Cinema Fire Pit Pets Views
Jeffersonville
10.0 out of 10, Exceptional, (28 reviews)
"Great amenities! Came for what Louisville had to offer, and were surprised at all that Jeffersonville had too. Great place to stay. "
United States
Marty C.
The price is NZ$3,099
includes taxes & fees
27 Aug - 28 Aug
Luxe Riverfront Newspaper Featured w/ Hot Tub Sauna Cinema Fire Pit Pets Views

14. Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (8 reviews)
"You won’t regret it! Private parking, quiet neighborhood, and fully stocked supplies for your stay! Easy check in and great hostess!"
United States
Sharonda
The price is NZ$396
includes taxes & fees
26 Aug - 27 Aug
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

15. ☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Jeffersonville
9.0 out of 10, Wonderful, (41 reviews)
"Very good host. The bathrooms could use some work but otherwise good value. "
United States
John O.
The price is NZ$760
includes taxes & fees
1 Sept - 2 Sept
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

16. 15 Min to Bourbon Fest | 4 En-Suites | Sleeps 10

15 Min to Bourbon Fest | 4 En-Suites | Sleeps 10
Deer Park
10.0 out of 10, Exceptional, (78 reviews)
"This property is perfect for 4 couples. Great property and great location."
United States
Cooper F.
The price is NZ$1,302
includes taxes & fees
16 Aug - 17 Aug
15 Min to Bourbon Fest | 4 En-Suites | Sleeps 10

17. Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (151 reviews)
"Host were nice and friendly "
United States
Robert M.
The price is NZ$683
includes taxes & fees
16 Aug - 17 Aug
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

18. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (52 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is NZ$270
includes taxes & fees
17 Aug - 18 Aug
The Bellwether Hotel

19. Stunning Victorian Home - prime location minutes from Louisville

Stunning Victorian Home - prime location minutes from Louisville
Jeffersonville
9.8 out of 10, Exceptional, (30 reviews)
"We really enjoyed our stay. Close to everything!"
United States
cheryl n.
The price is NZ$987
includes taxes & fees
19 Aug - 20 Aug
Stunning Victorian Home - prime location minutes from Louisville

20. Amazing/Entire house 5 min away from the Airport

Amazing/Entire house 5 min away from the Airport
Hayfield Dundee
10.0 out of 10, Exceptional, (35 reviews)
"Nothing but positive things to say about this property. First, it is beautifully decorated in a very comfortable and welcoming way. Plenty of room to lounge, cook and entertain both indoors and outside. It was extremely clean and well stocked with everything you need for a stay. The location is great. Close to the highway, attractions, many bars, shops, and dining options. On top of all that, the host was so helpful, great in her communication, and really went above and beyond to ensure...
United States
Rebecca L.
The price is NZ$1,060
includes taxes & fees
30 Aug - 31 Aug
Amazing/Entire house 5 min away from the Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Rolling Hills Hotel Reviews

Find out more about Rolling Hills

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Rolling Hills holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Rolling Hills. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Rolling Hills. Seeing all the best attractions is bound to make you fall in love with Rolling Hills. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Rolling Hills short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Rolling Hills?

Yes, there are holiday rentals close to the most popular sights in Rolling Hills, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rolling Hills has to offer?

Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8: This holiday home rental outside of Rolling Hills is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with 1 hot tub and a selection of books.

What can I see and do in Rolling Hills?

While exploring the area, visit family-friendly sights like Louisville Zoo, or get outside and enjoy nature at E.P. Tom Sawyer State Park. In the wider area, you’ll find Springhurst Towne Center Shopping Center and Paddock Shops.

What are holiday rentals like in Rolling Hills?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rolling Hills. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.