Rolling Hills Vacation Rentals

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Our top choices for Rolling Hills vacation rentals

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (9 reviews)
"It was everything we needed."
United States
Carmen C.
The price is ¥12,264
¥42,147 total
includes taxes & fees
Mar 31 - Apr 1
St. Matthew’s - Walk to Shops & Restaurants

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, (143 reviews)
"Great Trip…We enjoyed the four (4) nights. Host was great and her Scones were a treat."
United States
Anonymous traveler
The price is ¥40,879
¥64,010 total
includes taxes & fees
Mar 31 - Apr 1
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
8.8 out of 10, Excellent, (41 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is ¥20,889
¥24,246 total
includes taxes & fees
Mar 31 - Apr 1
The Bellwether Hotel

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (14 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is ¥15,550
¥23,912 total
includes taxes & fees
Mar 31 - Apr 1
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (37 reviews)
"This is a great little place to stay! Close to the Exposition Center and a lot of other attractions. It is an older place but clean and comfortable. This is our second stay at this place. "
United States
jaggers959
The price is ¥16,833
¥42,984 total
includes taxes & fees
Mar 31 - Apr 1
Close to Everything in Louisville!!!

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, (19 reviews)
"Everything was outstanding!"
United States
John W.
The price is ¥28,567
¥44,694 total
includes taxes & fees
Mar 31 - Apr 1
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

A Cozy Cottage Near the Heart of All Louisville Attractions!

A Cozy Cottage Near the Heart of All Louisville Attractions!
Cloverleaf
10.0 out of 10, Exceptional, (383 reviews)
"Wonderful little place to stay for a weekend. 10/10 recommend staying here. Quiet and serene, and the hosts have thought of everything- very nicely equipped!"
United States
Amanda E.
The price is ¥23,085
¥30,515 total
includes taxes & fees
Mar 31 - Apr 1
A Cozy Cottage Near the Heart of All Louisville Attractions!

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

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (85 reviews)
"Very nice place"
United States
Seth B.
The price is ¥21,615
¥52,534 total
includes taxes & fees
Apr 1 - Apr 2
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Close to Ky Fairgrounds&Expo, Churchill Downs!

Close to Ky Fairgrounds&Expo, Churchill Downs!
Germantown
10.0 out of 10, Exceptional, (74 reviews)
"The amenities were great and the house was the perfect spot for our weekend getaway. "
United States
Janessa D.
The price is ¥13,245
¥32,157 total
includes taxes & fees
Apr 2 - Apr 3
Close to Ky Fairgrounds&Expo, Churchill Downs!

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, (121 reviews)
"Host met onsite, informed of details and was friendly and helpful. Good location and nicely remodeled older home w lots of updates. Would stay again. "
United States
Dale K.
The price is ¥20,840
¥37,588 total
includes taxes & fees
Mar 31 - Apr 1
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Clifton
10.0 out of 10, Exceptional, (32 reviews)
"Our stay was very pleasant, great location, lots of great restaurants. Tyler the host was was always available when we had an issue. "
United States
Max D.
The price is ¥8,496
¥27,538 total
includes taxes & fees
Apr 1 - Apr 2
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

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, (80 reviews)
"Great location, very clean!!!!"
United States
Matt W.
The price is ¥24,688
¥49,122 total
includes taxes & fees
Apr 6 - Apr 7
Charming house in one of Louisville's most coveted neighborhoods

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
South Louisville
10.0 out of 10, Exceptional, (26 reviews)
"Very clean place, easy check in, Felix was very nice and super responsive "
United States
Will J.
The price is ¥4,905
¥26,161 total
includes taxes & fees
Apr 1 - Apr 2
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay at this cottage. Very quiet and relaxing. We will definitely stay here again!"
United States
Jarrod H.
The price is ¥24,047
¥41,495 total
includes taxes & fees
Apr 12 - Apr 13
Carriage House, 7 minutes from downtown Louisville

Urban Explorer Pad | Near Downtown + Yard

Urban Explorer Pad | Near Downtown + Yard
Jeffersonville
9.0 out of 10, Wonderful, (42 reviews)
"Amazing stay, would stay again any time! Host was easy to communicate with and home was clean when we arrived and had everything needed for a wonderful stay!"
United States
Cameron J.
The price is ¥16,031
¥58,103 total
includes taxes & fees
Mar 31 - Apr 1
Urban Explorer Pad | Near Downtown + Yard

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is ¥8,657
¥22,977 total
includes taxes & fees
Apr 5 - Apr 6
Alfesco - Walkable Highlands Guesthouse

The Derby House - Relaxing retreat before and after the excitement of the Derby!

The Derby House - Relaxing retreat before and after the excitement of the Derby!
Louisville
9.6 out of 10, Exceptional, (18 reviews)
"Nice clean and quiet place! Close to down town Louisville! "
United States
Joe C.
The price is ¥29,657
¥65,312 total
includes taxes & fees
Apr 10 - Apr 11
The Derby House - Relaxing retreat before and after the excitement of the Derby!

Victorian Center Jeffersonville

Victorian Center Jeffersonville
Jeff
9.4 out of 10, Exceptional, (52 reviews)
"A beautiful old home. Very clean and comfortable. Extremely convenient to everything we had planned for the weekend. Definitely a place we would reserve again."
United States
LUCY G.
The price is ¥31,020
¥55,705 total
includes taxes & fees
Mar 31 - Apr 1
Victorian Center Jeffersonville

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
New Albany
10.0 out of 10, Exceptional, (40 reviews)
"Great home and great location with access to many things close by."
United States
Todd S.
The price is ¥11,222
¥31,702 total
includes taxes & fees
Apr 6 - Apr 7
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

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, (51 reviews)
"Great place!"
United States
Nakoma F.
The price is ¥30,459
¥66,429 total
includes taxes & fees
Apr 20 - Apr 21
Near Highways and a 20 Min Drive to Louisville's Main Attractions
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

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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?

Spacious 4-bedroom townhome with 2 car garage in perfect Louisville location: This vacation home rental outside of Rolling Hills offers a fireplace, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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.