Rolling Hills Holiday Rentals

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Our top choices for Rolling Hills holiday rentals

9.8 out of 10, Exceptional, (62)
"Host was responsive to all messages. The small home we stayed in was so cozy and clean. Directions on how to get there were clear and easy to follow. 10/10 would recommend."
United States
Haley V.
The price is AU$347
includes taxes & fees
29 Dec - 30 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
3.0 star property
10.0 out of 10, Exceptional, (1)
"Amy was wonderful and went above and beyond to make sure we had a great stay. She even left pancakes w/syrup for breakfast and pasta w/sauce in case we didn’t have time to go to the store! It’s the small things that really stick out such as leaving a bowl of snacks, a few beers in the fridge, a bottle of wine, fully stocked medicine cabinet in case you forgot something. She even put food and water out for the dog along with toys and a blanket! We loved being there and it was such a beautiful...
United States
Robin
The price is AU$513
includes taxes & fees
2 Jan - 3 Jan 2026
Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

Aparthotel in Tyler Park

The Bellwether Hotel
3.5 star property
8.8 out of 10, Excellent, (32)
"Spectacular room, fabulous decor, tasty cookies, quiet stay "
United States
Mark
The price is AU$183
includes taxes & fees
1 Jan - 2 Jan 2026
The Bellwether Hotel
8.6 out of 10, Excellent, (10)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is AU$228
includes taxes & fees
14 Jan - 15 Jan 2026
Alfesco - Walkable Highlands Guesthouse
2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
The price is AU$483
includes taxes & fees
5 Jan - 6 Jan 2026
The Sweet Retreat Wheelchair Accessible Historic Home
9.8 out of 10, Exceptional, (21)
"Great place "
United States
Scott L.
The price is AU$249
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Tree-Lined Carriage Home - Stay in Serenity!
10.0 out of 10, Exceptional, (47)
"Located near lovely parks on the river. There is very little traffic in this area, yet you are close to downtown.We've stayed here twice because it is so clean, comfortable, stylish, and relaxing. "
United States
Debbie B.
The price is AU$361
includes taxes & fees
3 Jan - 4 Jan 2026
Carriage House, 7 minutes from downtown Louisville
10.0 out of 10, Exceptional, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is AU$222
includes taxes & fees
10 Jan - 11 Jan 2026
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
10.0 out of 10, Exceptional, (18)
"The cabin was cozy and inviting with so much history, and the grounds are meticulously maintained and absolutely gorgeous. Don was very nice to talk to and we enjoyed the 2 house pups that would let us pet them. "
United States
Adam H.
The price is AU$421
includes taxes & fees
31 Dec - 1 Jan 2026
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
10.0 out of 10, Exceptional, (71)
"Great location! Walking distance to several restaurants. Neighborhood is quite and safe. "
United States
Tracy F.
The price is AU$290
includes taxes & fees
29 Dec - 30 Dec
Book for Derby! Close to Churchill & Expo Center!
10.0 out of 10, Exceptional, (22)
"Very clean place, easy check in, Felix was very nice and super responsive "
United States
Will J.
The price is AU$264
includes taxes & fees
11 Jan - 12 Jan 2026
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
10.0 out of 10, Exceptional, (50)
"Great place, well equipped property with everything you need."
United Kingdom
Niteen S.
The price is AU$556
includes taxes & fees
3 Jan - 4 Jan 2026
Near Highways and a 20 Min Drive to Louisville's Main Attractions
9.8 out of 10, Exceptional, (141)
"Our host were phenomenal. Made us feel right at home. I would highly recommend this place to anybody.!!"
United States
Corey D.
The price is AU$600
includes taxes & fees
4 Jan - 5 Jan 2026
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Aparthotel in Downtown Louisville

Stellar Suites
4.5 star property
9.6 out of 10, Exceptional, (117)
"Clean and great location "
United States
Greg
The price is AU$263
includes taxes & fees
14 Jan - 15 Jan 2026
Stellar Suites
10.0 out of 10, Exceptional, (22)
"Good rooms and clean place"
United States
Mufid S.
The price is AU$443
includes taxes & fees
29 Dec - 30 Dec
Southern Family Charmer - Perfect Space & Location with style and comfort!

Holiday Home in Camp Taylor

Close to Everything in Louisville!!!
9.4 out of 10, Exceptional, (37)
"Clean home and very friendly neighbors "
United States
Tranquilina G.
The price is AU$405
includes taxes & fees
29 Dec - 30 Dec
Close to Everything in Louisville!!!
9.6 out of 10, Exceptional, (24)
"We will stay here over and over again. It’s a lovely place that a perfect location."
United States
Jennifer H.
The price is AU$314
includes taxes & fees
14 Jan - 15 Jan 2026
Stylish House Walking Distance from the Fun of the Highlands!
9.8 out of 10, Exceptional, (29)
"The apartment is very cute. the location was great. I was within walking distance of many cool spots and only steps from the river. The host is very polite and friendly. I would recommend this to anyone looking to stay near Louisville."
United States
Holly W.
The price is AU$205
includes taxes & fees
29 Dec - 30 Dec
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
10.0 out of 10, Exceptional, (14)
"Property was very clean, smelt great, and spacious. Located in a nice neighborhood. Hosts were extremely accommodating and friendly. Would definitely stay here again if I'm back in the area for an overnight trip. "
United States
Mandy M.
The price is AU$239
includes taxes & fees
29 Dec - 30 Dec
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Aparthotel in Downtown Louisville

The Duke Hotel
2.0 star property
The price is AU$247
includes taxes & fees
29 Dec - 30 Dec
The Duke Hotel
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.
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Top Rolling Hills Hotel Reviews

Find out more about Rolling Hills

Everything you need to know about Rolling Hills holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rolling Hills holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rolling Hills holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rolling Hills holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rolling Hills. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rolling Hills holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rolling Hills holiday rentals we have selected for you start as low as AU$183 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rolling Hills rentals

At Expedia, we put the best Rolling Hills holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rolling Hills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rolling Hills holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rolling Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!: This holiday home rental outside of Rolling Hills is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 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 a garden and a selection of games.

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.