Rolling Hills Vacation Rentals

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Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Browse Select Rolling Hills Vacation Homes

Big Chill! 5br 2ba Walkable- Hot tub!
Terrace/patio

Big Chill! 5br 2ba Walkable- Hot tub!

2.0 star property
9.4 out of 10, Exceptional, (9)
"Everything was just like it said in description. Great property for my work stay. "
Big Chill! 5br 2ba Walkable- Hot tub!
The Chestnut - Nulu
Terrace/patio

The Chestnut - Nulu

2.0 star property
9.8 out of 10, Exceptional, (16)
"This is an awesome place to stay, felt like home. The beds are really comfortable. We made a great choice in choosing VRBO instead of hotel!!"
The price is CA $97
CA $264 total
includes taxes & fees
Jul 21 - Jul 22
The Chestnut - Nulu
Wanderlust - Hot tub / fire pit - Location!
Outdoor spa tub

Wanderlust - Hot tub / fire pit - Location!

10.0 out of 10, Exceptional, (3)
"4 guys in our group. We all had big comfy beds and enjoyed the hot tub and fire pit outside. Would recommend!"
Wanderlust - Hot tub / fire pit - Location!
Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly
Microwave, oven, stovetop, dishwasher

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly
The Caldwell - Germantown Highlands
Fridge, microwave, oven, stovetop

The Caldwell - Germantown Highlands

10.0 out of 10, Exceptional, (21)
"Very pleasant stay in a beautifully appointed,immaculate home. Definitely will book again!"
The price is CA $97
CA $264 total
includes taxes & fees
Jul 30 - Jul 31
The Caldwell - Germantown Highlands
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Fridge, microwave, oven, stovetop

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly

10.0 out of 10, Exceptional, (133)
"I hosted a group of employees in town for a large trade show and we could not have been happier with our choice to stay at Stonecote. Everyone was comfortable and had space for privacy, but it was a treat to be able to socialize at the end of every day somewhere besides a crowded restaurant or hotel lobby. Great experience for all and our hosts could not have been more gracious. We will be back next year!"
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Fridge, microwave, oven, stovetop

Newly Renovated Studio! Ideal location for walking to restaurants & shops

9.8 out of 10, Exceptional, (36)
"My teenage daughter and I stayed here for a volleyball tournament that was held at KICC. The location was perfect. Very short drive to the courts and many restaurants and stores were walkable from the house. Close to the airport too. This was perfect for our needs. "
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
Lobby

Family Friendly, Historic Mansion Row, **5 min from Louisville!**

10.0 out of 10, Exceptional, (37)
"Convent and accommodation was excellent for 10 "
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
3 BR Downtown Sanctuary! Huge back yard
TV, offices

3 BR Downtown Sanctuary! Huge back yard

8.8 out of 10, Excellent, (33)
"House was very nice"
The price is CA $152
CA $340 total
includes taxes & fees
Jul 21 - Jul 22
3 BR Downtown Sanctuary! Huge back yard
Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed
Terrace/patio

Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed

9.8 out of 10, Exceptional, (54)
"The property was very nice. Everything we wanted to do was less than a 20min drive from the property. Everyone had a great time!"
The price is CA $148
CA $553 total
includes taxes & fees
Jul 20 - Jul 21
Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed
Charming shotgun home, minutes from Churchill Downs, Expo Center & downtown
Outdoor dining

Charming shotgun home, minutes from Churchill Downs, Expo Center & downtown

9.6 out of 10, Exceptional, (29)
"House was clean and very nice. Description online was accurate and we enjoyed our stay very much!"
Charming shotgun home, minutes from Churchill Downs, Expo Center & downtown
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Property grounds

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

10.0 out of 10, Exceptional, (157)
"We loved the decor, coziness and location of this quaint property! It had everything we needed for a comfortable, fun stay in Louisville! We will definitely stay here again! "
The price is CA $245
CA $550 total
includes taxes & fees
Jul 28 - Jul 29
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Relaxing 4BR Haven by CozySuites
Fridge, microwave, oven, stovetop

Relaxing 4BR Haven by CozySuites

Relaxing 4BR Haven by CozySuites
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
TV, foosball, offices

New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

9.4 out of 10, Exceptional, (27)
"Great location and awesome place to stay. We all had a great time!"
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
DERBY CITY SPEAKEASY 3-story 4-bedroom Historic Mansion 2 mi to Whiskey Row-NULU
Fridge, microwave, oven, stovetop

DERBY CITY SPEAKEASY 3-story 4-bedroom Historic Mansion 2 mi to Whiskey Row-NULU

10.0 out of 10, Exceptional, (79)
"House is gorgeous. Proximity to downtown is great. Owners were very communicative and helpful. Can’t find anything bad to say at all. "
The price is CA $307
CA $656 total
includes taxes & fees
Jul 29 - Jul 30
DERBY CITY SPEAKEASY 3-story 4-bedroom Historic Mansion 2 mi to Whiskey Row-NULU
Equus: Work Friendly & Near Downtown
Dining

Equus: Work Friendly & Near Downtown

9.4 out of 10, Exceptional, (3)
"Beautiful home! Great location! Very clean! "
Equus: Work Friendly & Near Downtown
Kentucky holiday home with Hot Tub & pool In Louisville KY
Fridge, microwave, oven, stovetop

Kentucky holiday home with Hot Tub & pool In Louisville KY

9.2 out of 10, Wonderful, (20)
"Very nice house, plenty of space. Nice quite neighborhood, short drive to attractions & activities. "
Kentucky holiday home with Hot Tub & pool In Louisville KY
ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks
Fridge, microwave, oven, stovetop

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks

8.0 out of 10, Very good, (4)
"Great place for a get away with friends or family. A lot of extra perks that come along with the house. Along with cleanliness and easy check in process. Tyler is great to deal with and answer anytime we had a question about the property. Would definitely stay if we are back in the area. "
ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks
Charming Highlands Carriage House 2 beds/2bath NO POOL
Exterior

Charming Highlands Carriage House 2 beds/2bath NO POOL

10.0 out of 10, Exceptional, (79)
"Stacy was an excellent host. Space was great for 2 adults and our dog "
Charming Highlands Carriage House 2 beds/2bath NO POOL
Best Location!!! - Huge Historic Charm - 3BR-3BTH
3 bedrooms, iron/ironing board, WiFi

Best Location!!! - Huge Historic Charm - 3BR-3BTH

9.2 out of 10, Wonderful, (85)
"Very accommodating & clean. "
Best Location!!! - Huge Historic Charm - 3BR-3BTH
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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