Pendleton Vacation Rentals
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Vacation Rentals in Pendleton

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville KY
When you stay at this vacation home in Shelbyville, you'll be 11 minutes by car from The Outlet Shoppes of the Bluegrass.
Kitchen
Washer

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Pendleton KY
$212 nightly
The price is $234 total per night
$234 total
Dec 13 - Dec 14
Total with taxes and fees
Located in Pendleton, this vacation home is in a rural location, within a 15-minute drive of Morgan Conservation Park and LaGrange Main Street Visitor Center.
Kitchen
Washer

Spectacular waterfront house!
Prospect KY
Located in Prospect, this vacation home is on the waterfront, within a 15-minute drive of Ohio River Valley and Paddock Shops.
Hot Tub
Kitchen

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison IN
$213 nightly
The price is $245 total per night
$245 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
With a stay at this vacation home in Madison, you'll be within a 5-minute walk of Ohio River Valley and Ohio River.
Kitchen
Washer

Near Highways and a 20 Min Drive to Louisville's Main Attractions
Louisville KY
$309 nightly
The price is $358 total per night
$358 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at this vacation home in Louisville, you'll be a 1-minute walk from Beckley Creek Park and 12 minutes by foot from Barklands.
Kitchen
Washer

Madison's Only YURT Experience
Madison IN
With a stay at this vacation home in Madison, you'll be 6 mi (9.7 km) from Ohio River Valley and 7.4 mi (12 km) from Ohio River.
Hot Tub
Kitchen

Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon
Louisville KY
When you stay at this vacation home in Louisville, you'll be next to a golf course, within a 5-minute drive of Beckley Creek Park and Valhalla Golf Club.
Hot Tub
Kitchen

Red comfy cottage
Madison IN
With a stay at this vacation home in Madison, you'll be within a 5-minute drive of Zeddies Tennis Center and Clifty Falls State Park.
Pool
Hot Tub

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Shelbyville KY
When you stay at this vacation home in Shelbyville, you'll be within a 10-minute drive of UofL Health - Shelbyville Hospital and Shelby County Community Theatre.
Hot Tub
Washer

Bourbon Trail Retreat . Sleeps 10 + Hot Tub. In the Heart of the Bourbon Trail
Shelbyville KY
When you stay at this vacation home in Shelbyville, you'll be 10 minutes by car from The Outlet Shoppes of the Bluegrass.
Hot Tub
Washer

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover IN
$218 nightly
The price is $251 total per night
$251 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at this vacation home in Hanover, you'll be within a 5-minute drive of Zeddies Tennis Center and Ohio River Valley.
Kitchen
Washer
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.
Pendleton Vacation Rentals essential information
Accommodation | 204 Vacation Rentals |
|---|---|
Lowest Price | $234 |
Highest Price | $358 |
Popular accommodation | Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby, RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE, Spectacular waterfront house!, Glenda’s Overlook..everything you need to make visiting Madison a great getaway!, Near Highways and a 20 Min Drive to Louisville's Main Attractions, Madison's Only YURT Experience , Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon, Red comfy cottage , Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20, Bourbon Trail Retreat . Sleeps 10 + Hot Tub. In the Heart of the Bourbon Trail, The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!, Enchanting, energizing, and enjoyable! |

