Vacation rentals in Douglass Hills

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Top-rated vacation rentals in Douglass Hills

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Louisville

4.95 out of 5 average rating, 300 reviews

Captain's Cabin:Historic Romantic by Bourbon Trail

Your own log cabin on a wooded hillside overlooking a private lake with gourmet breakfast served to your door (on weekends)! It's been the location for Lifetime and Hallmark movies! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience

Jul 15 – 22

€ 290 per night
Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 149 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Dec 10 – 17

€ 161 per night
Guest favorite

Guest suite in Louisville

4.91 out of 5 average rating, 403 reviews

Your Cozy Louisville Hideaway in the Highlands

Newly renovated basement apartment in the Highlands. Safe, quiet neighborhood, dedicated off street parking and proximity to some of the best food, shopping and entertainment Louisville has to offer. Easy access to all things Louisville! -Downtown Louisville -Churchill Downs -YUM! Center -Olmstead Park -NULU -Urban Bourbon Trail -Bardstown Road -Germantown -Thriving Music and Art scene -Louisville Convention Center -Great dining and breweries -Louisville International Airport -UofL -And more!

Aug 10 – 17

€ 81 per night

Popular amenities for Douglass Hills vacation rentals

Stay near Douglass Hills's top sights

Havana Rumba Middletown32 locals recommend
Southeast Christian Church4 locals recommend
Mark's Feed Store29 locals recommend
Rumors Restaurant8 locals recommend
Zaxby's Chicken Fingers & Buffalo Wings3 locals recommend
LouVino Restaurant & Wine Bar8 locals recommend

Other great vacation rentals in Douglass Hills

Guest favorite

Home in Louisville

4.85 out of 5 average rating, 163 reviews

Private EAST END gem, minutes from everything!

May 19 – 26

€ 172 per night
Guest favorite

Tiny home in Shepherdsville

4.95 out of 5 average rating, 208 reviews

Cozy Tiny House Near Louisville

Jun 9 – 16

€ 108 per night
Guest favorite

Guesthouse in Louisville

4.9 out of 5 average rating, 296 reviews

AMAZING POOL HOUSE HOT TUB

Apr 23 – 30

€ 159 per night
Guest favorite

Cottage in Shelbyville

4.92 out of 5 average rating, 161 reviews

Cozy Cottage on Firefly Farm

Nov 15 – 22

€ 105 per night
Guest favorite

Farm stay in La Grange

4.95 out of 5 average rating, 621 reviews

The Cottage at StoneLedge 2 bedroom/1bath

Jul 24 – 31

€ 160 per night
Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 103 reviews

Action City! Extravaganza at Bardstown Rd!

Jul 4 – 11

€ 102 per night
Guest favorite

Home in Louisville

4.9 out of 5 average rating, 170 reviews

Quiet Neighborhood Home With Outstanding Location

Nov 27 – Dec 4

€ 118 per night
Guest favorite

Guest suite in Louisville

4.96 out of 5 average rating, 28 reviews

Middletown Private Guest House

May 29 – Jun 5

€ 101 per night
Guest favorite

Cabin in Louisville

5.0 out of 5 average rating, 65 reviews

Historic Cabin by Bourbon Trail

Aug 1 – 8

€ 210 per night
Guest favorite

Apartment in Saint Matthews

5.0 out of 5 average rating, 75 reviews

Swanky Fully Equipped St. Matthews Apartment

Oct 29 – Nov 5

€ 128 per night
Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 75 reviews

Buechel Beauty

May 26 – Jun 2

€ 83 per night
Guest favorite

Guest suite in Windy Hills

4.93 out of 5 average rating, 40 reviews

Comfy Getaway Guest Suite in Louisville

Oct 4 – 11

€ 116 per night

Destinations to explore