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Rolling Hills Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Rolling Hills vacation rentals

A multi-story hotel with a flat facade, a parking lot in front, and a sign indicating 'STUDIOS.'

1. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (4 reviews)
"Was great enjoyed our stay and time there"
United States
Tammy
$99 nightly
The price is $116
Sep 12 - Sep 13
Total with taxes and fees
StudioRes by Marriott Louisville East
A two-story house with a green door, a front porch with a bench, and a brick chimney.

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

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
$295 nightly
The price is $342
Oct 5 - Oct 6
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants
A brick building with arched windows and a sign reading "The Bellwether."

3. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (54 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
$123 nightly
The price is $142
Sep 7 - Sep 8
Total with taxes and fees
The Bellwether Hotel
A garden with a stone bench, a decorative dragon statue, and various plants.

4. 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, (134 reviews)
"It was a great stay the property was super clean and the property manager was great!"
United States
Cole T.
$203 nightly
The price is $236
Sep 7 - Sep 8
Total with taxes and fees
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
A modern kitchen with a large window, a dining area with a table and chairs, and a view of the outdoors.

5. 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, (86 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
$300 nightly
The price is $348
Sep 8 - Sep 9
Total with taxes and fees
Charming house in one of Louisville's most coveted neighborhoods
A modern living room with a large window overlooking a lake, a sofa with patterned cushions, a glass coffee table, and a lamp.

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, (216 reviews)
"Beautiful location…very relaxing after a busy day!"
United States
Jim N.
$324 nightly
The price is $376
Sep 23 - Sep 24
Total with taxes and fees
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
A living room with a sofa, coffee table, and a dining area with chairs and a table.

7. 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.
$395 nightly
The price is $458
Sep 7 - Sep 8
Total with taxes and fees
OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr
A hotel room with two beds, a desk, and a chair.

8. 2 Queen Beds|Nsmk,Micfridge

2 Queen Beds|Nsmk,Micfridge
Jeffersonville
10.0 out of 10, Exceptional, (272 reviews)
"Comfortable beds gave us good sleep each night,a key part of any trip!"
United States
Anonymous traveler
$51 nightly
The price is $58
Sep 13 - Sep 14
Total with taxes and fees
2 Queen Beds|Nsmk,Micfridge
A living room with a sofa, armchair, coffee table, and a dining area with a table and chairs.

9. The Whiskey Stop! A Spacious Highlands Retreat

The Whiskey Stop! A Spacious Highlands Retreat
Germantown
10.0 out of 10, Exceptional, (78 reviews)
"It was perfect for our stay very comfortable and we enjoyed it very much"
United States
Lester W.
$161 nightly
The price is $173
Sep 7 - Sep 8
Total with taxes and fees
The Whiskey Stop! A Spacious Highlands Retreat
A modern living room with a sofa, coffee table, TV, and wooden cabinet.

10. 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
$217 nightly
The price is $245
Sep 8 - Sep 9
Total with taxes and fees
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
A modern hotel lobby with a reception desk, seating area, and a staircase leading to the upper floor.

11. Stellar Suites

Stellar Suites
4.5 star property
Downtown Louisville
9.6 out of 10, Exceptional, (147 reviews)
"Great location. Lots to do in the area. Room was clean and very nice."
United States
Brad
$156 nightly
The price is $182
Sep 7 - Sep 8
Total with taxes and fees
Stellar Suites
A rustic room with stone walls, a fireplace, leather armchairs, and a wooden ceiling.

12. 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, (26 reviews)
"Everything was outstanding!"
United States
John W.
$241 nightly
The price is $280
Sep 13 - Sep 14
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
A kitchen with dark wooden cabinets, stainless steel appliances, granite countertops, and pendant lighting.

13. American Pharoah Twin Spires Suite

American Pharoah Twin Spires Suite
Jeffersonville
10.0 out of 10, Exceptional, (6 reviews)
"Great place in downtown Jeffersonville. Clean and great location for Abbey Road on the River. Just had a few suggestions for mgr, im sure he'll consider. We'd def stay here again!"
United States
doris S.
$140 nightly
The price is $143
Sep 7 - Sep 8
Total with taxes and fees
American Pharoah Twin Spires Suite
A bedroom with a wooden bed, bedside tables, a nightstand, a window with blinds, and a wall-mounted lamp.

14. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
$231 nightly
The price is $266
Sep 8 - Sep 9
Total with taxes and fees
Convenient & Cozy! Close to everything Louisville!
A modern living room with a sofa, coffee table, fireplace, television, and a kitchen area in the background.

15. Spacious and cozy Highlands unit near attractions!

Spacious and cozy Highlands unit near attractions!
Germantown
10.0 out of 10, Exceptional, (144 reviews)
"Great place to stay, would definitely recommend to anyone looking to stay in Louisville "
United States
Andy T.
$176 nightly
The price is $188
Sep 6 - Sep 7
Total with taxes and fees
Spacious and cozy Highlands unit near attractions!
A wooden sauna with benches, a window with a view, and a hanging basket.

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

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (96 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.
$299 nightly
The price is $341
Sep 7 - Sep 8
Total with taxes and fees
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
A single-story house with a front porch, a garage door, and a small garden with a fence.

17. Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.4 out of 10, Exceptional, (27 reviews)
"Nice location and a lovely house"
United States
Juliana S.
$197 nightly
The price is $228
Sep 6 - Sep 7
Total with taxes and fees
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
A hotel room with a large bed, a nightstand, a lamp, and a potted plant.

18. Rooftop Patio & Games in Historic Highlands

Rooftop Patio & Games in Historic Highlands
Cherokee Triangle
9.2 out of 10, Wonderful, (14 reviews)
"2 friends trip on the Bourbon trail. The Highlands neighborhood is a safe and vibrant area, several options for coffee, breakfast, and lunch. Definitely have dinner at MeeshMeesh when you're in town!"
United States
Chris E.
$194 nightly
The price is $209
Sep 6 - Sep 7
Total with taxes and fees
Rooftop Patio & Games in Historic Highlands
A modern kitchen with a central island, bar stools, pendant lights, and a large window with curtains.

19. The Shotgun Rye! Your Bourbon home near Downtown

The Shotgun Rye! Your Bourbon home near Downtown
Germantown
10.0 out of 10, Exceptional, (78 reviews)
"Great location within driving distance to all the tourist destinations. Easy parking and all the amenities you would need! Would def stay again!"
United States
Jered J.
$176 nightly
The price is $188
Sep 7 - Sep 8
Total with taxes and fees
The Shotgun Rye! Your Bourbon home near Downtown

20. Riverside Suite: Walk to Big Four Bridge &

Riverside Suite: Walk to Big Four Bridge &
Jeffersonville
9.6 out of 10, Exceptional, (44 reviews)
"Awesome little spot "
United States
Paul G.
$168 nightly
The price is $179
Sep 7 - Sep 8
Total with taxes and fees
Riverside Suite: Walk to Big Four Bridge &
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

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

10/10 Excellent
"Property was nice and well maintained. Loved seeing the horses !Our room was fabulous and very clean ! Casino is great too, but felt that it could use some basic old time machines as well. We came in from Indiana for a break from the storm aftermath. It was so nice to be greeted by someone as wonderful and welcoming as Harry ! After all we had been through he made our much needed getaway great from the beginning ! I"
Kristin 2-night trip
Posted 4 hours ago
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Find out more about Rolling Hills

Everything you need to know about Rolling Hills vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rolling Hills vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rolling Hills vacation 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 low season months. For more hustle and bustle, you may prefer to visit Rolling Hills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $116 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rolling Hills rentals

At Expedia, we put the best Rolling Hills vacation 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 vacation.

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 vacation rentals in Rolling Hills?

Yes, there are vacation rentals near well known points of interest in Rolling Hills, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Rolling Hills?

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville: This vacation home rental outside of Rolling Hills is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

What can I see and do in Rolling Hills?

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

What are vacation rentals like in Rolling Hills?

Vacation rentals are private properties you can stay in for several days or longer in Rolling Hills. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.