Holiday rentals in Douglass Hills

Bourbon Trail Estate | 3 Epic Acres | 7 Bed 6 Bath

Welcome to your ultimate Louisville getaway! 🏡 This private 5BR retreat blends space, comfort, and style with unbeatable access to the Bourbon Trail, dining, and attractions—perfect for families or groups. ✨ Spacious 5BR, 5.5BA Retreat – 7 beds (5 Kings) 🛏️ 🍳 3 Full Kitchens + Bar 🎬 Entertainment Room w/ Media System – Perfect for Game Night 🎮 🌳 Private Backyard for Dining & Relaxing 🥃 Quiet setting just minutes from Bourbon Trail, Shopping & Top Attractions A serenity-meets-convenienc

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

Unique Serenity - Entire Home On Private 3-Acres

A perfect place for family and friends to spend time together. This unique home is spacious and sits on 3-acres well-maintained property. You can enjoy all the local shops, restaurants, parks, and golf courses while staying in what feels like a secluded country-side setting. 4br, 4ba, large kitchen and dining area with granites throughout. Large covered porch for outdoor enjoyment. 4 smart tv's, high speed wifi, washer/dryer, and iron are provided. Sleeps 12+. RVs and trailers welcome.

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Perfect for Work or Play, Close to Everything!

Whether you're here for work or play, our Airbnb offers the perfect base for your Kentucky adventures! Welcome to your home away from home! Nestled in the quiet suburbs, our modern & spacious retreat offers the perfect blend of comfort & convenience. Whether you’re here to explore the famous Bourbon Trail, work remotely, or simply unwind, you’ll find everything you need right here! Close to shopping, dining, entertainment, major highways, top bourbon distilleries and downtown Louisville.

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!

Location to xway, covered porch & grill, parking

Fully furnished house, Full kitchen with all appliances and w/d. Leather furniture, hardwood floors throughout. Covered front and back porch , park at your back door. Located 1 mile from 1-265 or 1-264 at the Blankenbaker exit. Clean and spacious, bungalow in the heart of Middletown , close to restaurants, shops, Southeast Christian Church., Parks, & entertainment .Most pets accepted but xtra fees are applicable . Lease can be extended, and other available properties nearby.

SuperHost ~ Beautiful NEW Condo Near Louisville!

🎯 Prime Location in Douglass Hills, KY 🏡 Minutes from Louisville – Perfect for a peaceful stay with quick access to city attractions 🐎 Close to Churchill Downs & the Derby Museum – A must for horse racing fans and history lovers! 🛍 Near Oxmoor Center & Mall St. Matthews – shopping, dining, and entertainment. 🚗 Easy Access to I-64 & I-264 – Convenient travel to Louisville, the airport, and local parks. 🛏 Book now and enjoy your Kentucky getaway!

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Newly Updated: Spacious Suite/Private Entry

My guest suite is close to restaurants, business parks, shopping and easy access to highways. Guests love this place because of the big trees, green space and private entrance. The patio is great for sipping morning coffee, reading or enjoying an evening beverage. Beautiful, quiet neighborhood is perfect for a walk/run. This spacious, comfortable suite is good for couples, solo adventurers, business travelers and small families.