Holiday Rentals in Oldham County

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Our top choices for Oldham County holiday rentals

Terrace/patio

Pendleton, KY Farm in Oldham Co

Pendleton, KY Farm in Oldham Co
Pendleton
10.0 out of 10, Exceptional, (4 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 €804
includes taxes & fees
16 May - 17 May
Pendleton, KY Farm in Oldham Co
Dining

4BR Estate: Heated Pool & Hot Tub, 5 King Beds

4BR Estate: Heated Pool & Hot Tub, 5 King Beds
La Grange
10.0 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay!"
United States
Katie H.
The price is €841
includes taxes & fees
17 May - 18 May
4BR Estate: Heated Pool & Hot Tub, 5 King Beds
Exterior detail

The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (5 reviews)
"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 Sweet Retreat Wheelchair Accessible Historic Home
Pool

Exclusive Farmhouse w/ a Romantic Garden View!

Exclusive Farmhouse w/ a Romantic Garden View!
Prospect
10.0 out of 10, Exceptional, (1 review)
"Scenic horse farm. Secluded, private, and quiet. I couldn't be happier with the accommodations. Would like to return when in the area."
United States
Darlene N.
The price is €172
includes taxes & fees
13 May - 14 May
Exclusive Farmhouse w/ a Romantic Garden View!
Property grounds

Exclusive Buckner retreat w/ theater & game room!

Exclusive Buckner retreat w/ theater & game room!
Buckner
The price is €369
includes taxes & fees
11 May - 12 May
Exclusive Buckner retreat w/ theater & game room!
Front of property

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (47 reviews)
"Unique and beautiful hotel in a great area. Would highly recommend."
United States
Erika
The price is €133
includes taxes & fees
1 Jun - 2 Jun
The Bellwether Hotel
Exterior

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, (144 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is €346
includes taxes & fees
6 May - 7 May
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Outdoor spa tub

House Downtown with Hot Tub Fire Pit and Speakeasy

House Downtown with Hot Tub Fire Pit and Speakeasy
Shelbyville
10.0 out of 10, Exceptional, (19 reviews)
"Overall great value and accommodations. Would highly recommend this property."
United States
Chad K.
The price is €632
includes taxes & fees
10 May - 11 May
House Downtown with Hot Tub Fire Pit and Speakeasy
Exterior

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (80 reviews)
"We brought a large group to a conference in Louisville and it was perfect to have all of us stay together. It was a historic house, full of charm. Only negative was the warm water ran out quickly with so many people."
United States
Benjamin T.
The price is €1,070
includes taxes & fees
11 May - 12 May
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Outdoor pool, a heated pool

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, (389 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 €166
includes taxes & fees
13 May - 14 May
A Cozy Cottage Near the Heart of All Louisville Attractions!
Dining

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Jeffersontown
9.6 out of 10, Exceptional, (32 reviews)
"We had a wonderful experience. The house was great and had everything we needed. Everything was clean and well maintained. The host was very friendly, responsive, and flexible, which we really appreciated. Would definitely stay again!"
United States
Dieudonne N.
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Smart TV

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
9.8 out of 10, Exceptional, (41 reviews)
"The property was clean and the host was very responsive prior to and during the stay ensuring a positive trip. "
United States
Natalie H.
The price is €212
includes taxes & fees
10 May - 11 May
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (10 reviews)
"It was everything we needed."
United States
Carmen C.
The price is €352
includes taxes & fees
25 May - 26 May
St. Matthew’s - Walk to Shops & Restaurants
Fridge, microwave, oven, stovetop

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Louisville
10.0 out of 10, Exceptional, (82 reviews)
"Host was accommodating and welcoming. "
United States
Bobbie S.
The price is €211
includes taxes & fees
12 May - 13 May
Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Exterior

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Henryville
10.0 out of 10, Exceptional, (161 reviews)
"We had a great time during our stay. The cabin was as advertised and we were able to get some great family time together. "
United States
Amy M.
The price is €503
includes taxes & fees
6 May - 7 May
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Smart TV

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, (58 reviews)
"Nice friendly town and eating places"
United States
Paul P.
The price is €196
includes taxes & fees
6 May - 7 May
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (38 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 €231
includes taxes & fees
10 May - 11 May
Close to Everything in Louisville!!!
Interior

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 €244
includes taxes & fees
6 May - 7 May
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Bar (on property)

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (31 reviews)
"The VRBO was perfect. Has the elegant modern feel just like the pictures show and has lots of space to hang out and relax. Loved the location and how walkable it was to coffee shops, restaurants, and bars. Loved staying here and highly recommend!"
United States
Lucas L.
Unique Downtown Studio with an Industrial Vibe
Interior

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)
"Great location to get around town via i65. Plenty of offerings nearby for stores and food. Look forward to staying again. "
United States
Charles D.
The Derby House - Relaxing retreat before and after the excitement of the Derby!
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 Oldham County Hotel Reviews

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

8/10 Good
"The breakfast could’ve been better. I wished I ordered something instead of doing the buffet"
Kelly 1-night trip
Posted less than an hour ago
Crowne Plaza Louisville Airport Expo Ctr by IHG

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Holiday Homes in Oldham County

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