Douglass Hills holiday rentals

We found 820 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Douglass Hills to find one that's perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a hot tub and garden. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Douglass Hills

Showing deals for:1 Jan - 8 Jan

Interior
Exterior
Living area
Terrace/patio
Exceptional
(87 reviews)

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

Louisville

8% off
AU$10,178
for 7 nights, 1 home
AU$1,454 per night
includes taxes & fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Dining
Exterior
Terrace/patio
Private kitchen
Exceptional
(11 reviews)

Castle St Matthews

Louisville

8% off
AU$13,173
for 7 nights, 1 home
AU$1,882 per night
includes taxes & fees
Castle St Matthews
Interior
Private kitchen
Pool
New separete entrance to a new addition
Exceptional
(24 reviews)

Spacious 5BR Getaway – Pool, Patios & Fun

Louisville

8% off
AU$11,554
for 7 nights, 1 home
AU$1,651 per night
includes taxes & fees
Spacious 5BR Getaway – Pool, Patios & Fun
Interior
Private kitchen
Room
Living area
Exceptional
(35 reviews)

❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast

Prospect

17% off
AU$57,806
for 7 nights, 1 home
AU$8,258 per night
includes taxes & fees
❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast
Foyer as you walk in front door
Exterior
Family room off of foyer and next to Living room area 1 with queen bed And bunks
Living room area 1 with queen bed and bunk beds
Exceptional
(14 reviews)

Beautiful views and sunrises overlooking the water. Spacious home with elevator.

Jeffersonville

20% off
AU$5,568
for 7 nights, 1 home
AU$795 per night
includes taxes & fees
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Dining room view 1
Kitchen view 2
Master bedroom view 2
Kitchen view 3
Exceptional
(49 reviews)

Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon

Louisville

8% off
AU$4,572
for 7 nights, 1 home
AU$653 per night
includes taxes & fees
Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon
Front of the house with ample parking...
To make it even more special for you, we have a 6 people private hottub with lovely views of the Ohio river!
As you open the door, this is the view you will be walking into.
State-of-the-art open layout kitchen with all stainless steel appliances including an oven, microwave, dishwasher, duo instapot with airfryer, and tones of pots pans, cookware, bakeware & dinnerware.
Exceptional
(28 reviews)

Newspaper Featured Luxe Riverfront w/ Fire Pit Hot Tub Cinema Sauna Pets Views

Jeffersonville

7% off
AU$8,181
for 7 nights, 1 home
AU$1,169 per night
includes taxes & fees
Newspaper Featured Luxe Riverfront w/ Fire Pit Hot Tub Cinema Sauna Pets Views
Living area
Terrace/patio
Room
Dining
Exceptional
(23 reviews)

Enchanted Cabin at LedgeRock Springs

Louisville

7% off
AU$6,109
for 7 nights, 1 cabin
AU$873 per night
includes taxes & fees
Enchanted Cabin at LedgeRock Springs
Living area
Pool
Living area
Exterior
Exceptional
(11 reviews)

Safe, scenic, and convenient. Bordering a State Park!

Louisville

13% off
AU$5,658
for 7 nights, 1 home
AU$808 per night
includes taxes & fees
Safe, scenic, and convenient. Bordering a State Park!
Back of house with new walkway and deck.
View from kitchen toward dining room.
Brand new dining room with views of deck, side and backyard.
Front of house.
Exceptional
(87 reviews)

Charming house in one of Louisville's most coveted neighborhoods

Louisville

8% off
AU$2,801
for 7 nights, 1 home
AU$400 per night
includes taxes & fees
Charming house in one of Louisville's most coveted neighborhoods
Interior
Exterior
Room
Interior
Exceptional
(147 reviews)

Ultimate Getaway: Expansive Home with Hot Tub & Relaxation

Louisville

7% off
AU$7,241
for 7 nights, 1 home
AU$1,034 per night
includes taxes & fees
Ultimate Getaway: Expansive Home with Hot Tub & Relaxation
Dining
Exterior
Interior
Private kitchen
Exceptional
(6 reviews)

3-bedroom condo in Norton Commons

Prospect

8% off
AU$3,693
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
3-bedroom condo in Norton Commons
Dresser and closet for clothes storage. 
(There is a wall at the top of stairs)
Desk for working remotely. Portable closet, iron and ironing bord provided.
Queen pull-out bed, 55" tv with hulu, prime, apple tv, hbo, Disney +, Netflix
Brand new, full kitchen. Dishwasher, stove/oven, microwave, toaster, fridge
Exceptional
(53 reviews)

Newly Renovated Studio! Ideal location for walking to restaurants & shops

Louisville

15% off
AU$1,234
for 7 nights, 1 home
AU$176 per night
includes taxes & fees
Newly Renovated Studio! Ideal location for walking to restaurants & shops
1st floor sunroom TV
Living area
Living area
Front
Excellent
(10 reviews)

Lovely Gem in the Vibrant Highlands close to it all!

Louisville

8% off
AU$9,422
for 7 nights, 1 home
AU$1,346 per night
includes taxes & fees
Lovely Gem in the Vibrant Highlands close to it all!
Private entrance from porch, beamed ceiling, antique furnishings.
Front porch where you can have your gourmet breakfast and enjoy nature.
Bedroom view of lake and woods. The hammock awaits you!
Creek on property
Exceptional
(22 reviews)

Captain's Annex; close to Bourbon Trail and Churchill Downs, far from ordinary!

Louisville

8% off
AU$1,758
for 7 nights, 1 home
AU$251 per night
includes taxes & fees
Captain's Annex; close to Bourbon Trail and Churchill Downs, far from ordinary!
Terrace/patio
Exterior
Private kitchen
Private kitchen
Exceptional
(10 reviews)

Spacious house next to Mellwood Arts Center; Amazing downtown views! HOT TUB!

Louisville

6% off
AU$7,858
for 7 nights, 1 home
AU$1,123 per night
includes taxes & fees
Spacious house next to Mellwood Arts Center; Amazing downtown views! HOT TUB!
Living area
Front of house - just steps from "Restaurant Row" on Bardstown Road.
Relax on the front porch with a cool drink.
Room
Exceptional
(173 reviews)

Elegant Home Steps to Restaurant Row!

Louisville

7% off
AU$2,509
for 7 nights, 1 home
AU$358 per night
includes taxes & fees
Elegant Home Steps to Restaurant Row!
Bedroom #2
Living room w/pullout bed
Kitchen sotcked
Outdoor casual decking area
Exceptional
(29 reviews)

Louisville GEM, newly furnished, super clean, in a safe trendy area

Louisville

11% off
AU$1,612
for 7 nights, 1 apartment
AU$230 per night
includes taxes & fees
Louisville GEM, newly furnished, super clean, in a safe trendy area
Private kitchen
Living area
Interior
Private kitchen
Exceptional
(131 reviews)

The Cozy Bungalow-Historic Highlands-Bardstown Rd

Louisville

7% off
AU$4,397
for 7 nights, 1 home
AU$628 per night
includes taxes & fees
The Cozy Bungalow-Historic Highlands-Bardstown Rd
Interior
Private kitchen
Interior
Living area
Exceptional
(30 reviews)

Buddha's Bungalow above the Highlands

Louisville

7% off
AU$2,853
for 7 nights, 1 apartment
AU$408 per night
includes taxes & fees
Buddha's Bungalow above the Highlands
Room
Interior
Private kitchen
Interior
Wonderful
(14 reviews)

Rooftop Patio & Games in Historic Highlands

Louisville

15% off
AU$1,607
for 7 nights, 1 apartment
AU$230 per night
includes taxes & fees
Rooftop Patio & Games in Historic Highlands
Top of steps and enjoy some local art
Interior
Living area
Property grounds
Exceptional
(127 reviews)

Charming Private Bungalow with EV Charger Near Downtown Louisville

Louisville

11% off
AU$1,712
for 7 nights, 1 home
AU$245 per night
includes taxes & fees
Charming Private Bungalow with EV Charger Near Downtown Louisville
Private kitchen
Living area
Dining
Interior
Exceptional
(40 reviews)

Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi

Louisville

15% off
AU$1,355
for 7 nights, 1 home
AU$194 per night
includes taxes & fees
Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
Private kitchen
Room
Living area
Interior
Exceptional
(38 reviews)

Charming Clifton Loft with Balcony & Free

Louisville

19% off
AU$1,389
for 7 nights, 1 apartment
AU$198 per night
includes taxes & fees
Charming Clifton Loft with Balcony & Free
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Head to the lively city of Douglass Hills

The area's live music and museums are just some of the reasons to come on holiday to Douglass Hills. This city is well-known for its shopping and cafes. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Douglass Hills

Are you looking for attractions to see in the city? Venture out of your holiday home and experience everything that makes Douglass Hills a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Valhalla Golf Club (4.4 mi / 7.1 km)
  • Louisville Zoo (8.6 mi / 13.8 km)
  • Kentucky Kingdom (10.9 mi / 17.6 km)
  • Churchill Downs (12.1 mi / 19.5 km)
  • Polo Fields Golf and Country Club (6.2 mi / 10 km)
  • Atlantis Waterpark (11.5 mi / 18.6 km)

Exploring the natural landscape of Douglass Hills

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Douglass Hills is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • E.P. Tom Sawyer State Park (3 mi / 4.8 km)
  • Beckley Creek Park (4.7 mi / 7.5 km)
  • Cherokee Park (7.7 mi / 12.4 km)
  • Yew Dell Botanical Gardens (8.5 mi / 13.6 km)
  • Louisville Mega Cavern (8.6 mi / 13.8 km)
  • Louisville Waterfront Park (9.4 mi / 15.1 km)

Travelling to and around Douglass Hills

The nearest airport is in Louisville International Airport (SDF), located 10.9 mi (17.5 km) from the city centre.

Frequently asked questions

What is the best area to stay in Douglass Hills when booking a holiday rental?
When considering a holiday rental in Douglass Hills, Kentucky, the area is known for its charming residential feel and proximity to various attractions. The neighbourhood is particularly appealing for those looking for a peaceful retreat while still being close to the vibrant city life of nearby Louisville.Douglass Hills itself offers a selection of properties, ranging from cosy homes to more spacious options, making it suitable for families and groups alike. One of the top attractions in the vicinity is the nearby Oxmoor Centre, which is a popular shopping destination featuring a variety of retail stores and dining options. Additionally, the lovely parks in the area, such as the scenic Douglass Hills Park, provide a great place for outdoor activities and relaxation.For those keen on exploring a bit further, the attractions of Louisville are just a short drive away, including the renowned Louisville Zoo and the historic Churchill Downs, famous for the Kentucky Derby.
What are the top attractions in Douglass Hills?
Douglass Hills is primarily a residential area, but it offers convenient access to several attractions nearby. The neighbourhood itself features lovely parks, such as Douglass Hills Park, which has walking trails and playgrounds for families. Just a short drive away, visitors can explore the expansive Jefferson Memorial Forest, which provides hiking opportunities and beautiful natural scenery.For shopping and dining, the nearby Mall St. Matthews offers a variety of retail options and restaurants, making it a popular spot for locals and visitors alike.
Are all fees included in the Douglass Hills holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Douglass Hills holiday homes with parking?
Stayz offers a wide selection of holiday homes in Douglass Hills with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Douglass Hills holiday homes?
You can find great discounts on holiday homes in Douglass Hills on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Douglass Hills holiday home booking on Stayz?
To find Douglass Hills holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Douglass Hills?
A long-stay holiday home in Douglass Hills is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Douglass Hills holiday home?
Book your Douglass Hills holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Douglass Hills?
Prices for holiday homes in Douglass Hills vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Douglass Hills to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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