Holiday Homes in Pendleton

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Find holiday rentals that suit your style

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Apartments
Apartments
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Cabins
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Pendleton holiday homes

A covered patio with a brick wall, outdoor seating, and string lights.

1. Pendleton, KY Farm in Oldham Co

Pendleton, KY Farm in Oldham Co
Pendleton
10.0 out of 10, Exceptional, (6 reviews)
"The house was perfect for our group of 8. Very clean, great gathering space inside and out and well maintained. Highly recommended! Thanks Betty!"
United States
Scott B.
The price is AU$2,252
includes taxes & fees
10 Nov - 11 Nov
Pendleton, KY Farm in Oldham Co
A wooden deck with a green door, wicker chairs, and a small table.

2. The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (7 reviews)
"I loved having the travel crib and high chair available for my kids! Everything was clean and the host made everything a breeze!"
United States
Samantha C.
The price is AU$631
includes taxes & fees
15 Nov - 16 Nov
The Sweet Retreat Wheelchair Accessible Historic Home
A spacious dining area with a large table set for six, surrounded by modern chairs. A chandelier hangs from the ceiling, and a staircase leads to an upper level. The kitchen in the background features white cabinets and a central island.

3. Estate: Heated Pool, Hot Tub, Game Rooms, Pets

Estate: Heated Pool, Hot Tub, Game Rooms, Pets
La Grange
10.0 out of 10, Exceptional, (29 reviews)
"My family enjoyed the house. We loved the pool and hot tub and there were so many other things we could do while staying in the house. The kids loved all of the games and the karaoke. The house fit our needs perfectly and the hosts were very kind and helpful."
United States
Linda L.
The price is AU$1,267
includes taxes & fees
9 Nov - 10 Nov
Estate: Heated Pool, Hot Tub, Game Rooms, Pets
A house with a fire pit and Adirondack chairs in the yard.

4. Exclusive Buckner retreat w/ theater & game room!

Exclusive Buckner retreat w/ theater & game room!
Buckner
6.0 out of 10, (1 review)
"The house was big enough for my family of 6. The yard was great for my children to run around and for us to sit around the fire at night. The theater room was nice for my children to hang out in. The game room was nice to play pool in but unfortunately the darts for the dart board were in sad shape so we couldn't utilize that. The home gym was nice to workout in. Unfortunately we walked into ants all over the kitchen pantry and on the counters. We contacted the host (company) right away and they...
United States
Jenn M.
The price is AU$755
includes taxes & fees
15 Nov - 16 Nov
Exclusive Buckner retreat w/ theater & game room!
A modern kitchen with a dining area, built-in shelves, and a green sofa in the living room.

5. Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"Very convenient for Horse Show we were attending. Everything was as described and the hosts were very accommodating. "
United States
Marlena J.
The price is AU$478
includes taxes & fees
15 Nov - 16 Nov
Quiet Downtown Maple Cottage Gem
A bedroom with a bed, a dresser, two doors, a ceiling fan, and a painting on the wall.

6. The Shelby House | Historic Charm, Modern Comfort

The Shelby House | Historic Charm, Modern Comfort
Shelbyville
The price is AU$387
includes taxes & fees
9 Nov - 10 Nov
The Shelby House | Historic Charm, Modern Comfort
A modern kitchen with a stainless steel sink, a built-in faucet, and a window overlooking a deck with outdoor seating.

7. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is AU$765
includes taxes & fees
15 Nov - 16 Nov
Spacious Bourbon retreat near Downtown Louisville!
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

8. 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, (29 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
The price is AU$219
includes taxes & fees
2 Dec - 3 Dec
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

9. Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (51 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is AU$406
includes taxes & fees
15 Nov - 16 Nov
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A covered outdoor patio with wicker furniture, a fire pit, and string lights.

10. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful, peaceful area and the cutest home! It was perfect for our large group and Iris was an incredible host. We definitely want to visit again!"
United States
Hannah G.
The price is AU$799
includes taxes & fees
9 Nov - 10 Nov
Kentucky Bourbon Trail: Hot Tub & Game Room
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

11. The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (55 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is AU$371
includes taxes & fees
9 Nov - 10 Nov
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A wooden cabin with a porch, a staircase, and a deck.

12. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is AU$226
includes taxes & fees
8 Dec - 9 Dec
Sassafras Woodland Cabin at Lost Trails
A covered porch with a wooden door, potted plants, and a metal railing.

13. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Lovely! We really enjoyed this amazing house!"
United States
Roxann W.
The price is AU$347
includes taxes & fees
9 Nov - 10 Nov
The Artist’s A-Frame
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

14. Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (80 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
The price is AU$339
includes taxes & fees
16 Nov - 17 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A two-story house with a garage, a stone facade, and a well-maintained lawn.

15. 3BR Home Near Hanover College & Madison

3BR Home Near Hanover College & Madison
Hanover
The price is AU$618
includes taxes & fees
15 Nov - 16 Nov
3BR Home Near Hanover College & Madison
A deck with a fire pit table and chairs, overlooking a body of water and forested area.

16. The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!

The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
Prospect
9.8 out of 10, Exceptional, (10 reviews)
"My family and I had a wonderful trip. The house was absolutely beautiful. Everything was clean and well taken care of we couldn’t have asked for a better vacation"
United States
Thomas c.
The price is AU$981
includes taxes & fees
7 Dec - 8 Dec
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
A two-story house with a front porch, columns, and a well-maintained lawn.

17. Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Shelbyville
10.0 out of 10, Exceptional, (25 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is AU$935
includes taxes & fees
15 Nov - 16 Nov
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A modern kitchen with a large window, a dining area with a table and chairs, and a view of the outdoors.

18. 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, (88 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
The price is AU$639
includes taxes & fees
10 Nov - 11 Nov
Charming house in one of Louisville's most coveted neighborhoods
A deck with two blue chairs and a table, overlooking a lake with trees and a distant bridge.

19. Riverstone Retreat | Ohio River Views + Hot Tub

Riverstone Retreat | Ohio River Views + Hot Tub
Prospect
The price is AU$866
includes taxes & fees
9 Nov - 10 Nov
Riverstone Retreat | Ohio River Views + Hot Tub
A spacious room with a fireplace, large windows, and a view of the outdoors.

20. Iconic Lighthouse Estate on Scenic Ohio River!

Iconic Lighthouse Estate on Scenic Ohio River!
Prospect
10.0 out of 10, Exceptional, (1 review)
"What an amazing property and an amazing owner to work with. We will definitely be looking to rebook should the property have vacancy on our next trip to Louisville."
United States
Sean S.
The price is AU$913
includes taxes & fees
30 Nov - 1 Dec
Iconic Lighthouse Estate on Scenic Ohio River!
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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