Westport Holiday Rentals

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Our top choices for Westport holiday rentals

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

Louisville
9.8 out of 10, Exceptional, (76)
"Interesting property!"
United States
Donald R.
The price is AU$1,873
includes taxes & fees
14 Dec - 15 Dec
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

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

Jeffersontown
9.6 out of 10, Exceptional, (25)
"Great place good time "
United States
Jefferey S.
The price is AU$1,129
includes taxes & fees
18 Dec - 19 Dec
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

You hit the exacta with location and comfort!! Right in the heart of St Matthews

2.0 star property
Saint Matthews
10.0 out of 10, Exceptional, (1)
"This house is fantastic and we could not have asked for better hosts for our Louisville visit. Our kids loved being able to walk to restaurants and shops right there in St Matthews, and location is convenient to everything in Louisville. Would stay there again!"
United States
Andrew E.
You hit the exacta with location and comfort!! Right in the heart of St Matthews

Spectacular waterfront house!

Prospect
9.6 out of 10, Exceptional, (86)
"Great location with views of the river. "
United States
Patrick G.
Spectacular waterfront house!

stayAPT Suites Louisville North-Clarksville

4.0 star property
Clarksville
9.8 out of 10, Exceptional, (43)
"Excellent stay. One of my favorite hotels in the area. They never disappoint "
United States
Julia
The price is AU$266
includes taxes & fees
12 Dec - 13 Dec
stayAPT Suites Louisville North-Clarksville

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

Louisville
10.0 out of 10, Exceptional, (189)
"Way beyond our expectations. We loved our stay!"
United States
Eric M.
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

Cozy Derby Home 2 Bedroom Shotgun style home, with Large Adorable Loft

Crescent Hill
9.8 out of 10, Exceptional, (9)
"Was perfect for our 5 day stay while my daughter had a basketball tournament at the Exposition Center. This house has everything you need and the host was amazing will definitely stay here again if i come this way in the future!"
United States
Cami S.
Cozy Derby Home 2 Bedroom Shotgun style home, with Large Adorable Loft

Cozy Tree-Lined Carriage Home - Stay in Serenity!

Louisville
9.8 out of 10, Exceptional, (19)
"Nice place to stay"
United States
Terry M.
The price is AU$252
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Tree-Lined Carriage Home - Stay in Serenity!

Dream Location of Louisville 5 to 20 minutes to anywhere

Rockcreek Lexington Road
9.6 out of 10, Exceptional, (25)
"Very nice. Had a great stay!"
United States
Forrest P.
Dream Location of Louisville 5 to 20 minutes to anywhere

1847 Log Home with modern comfort. Near Louisville & Bourbon Trail

Louisville
10.0 out of 10, Exceptional, (147)
"Great place to stay and an even better host. Tim was great from start to finish. Making us feel like we were at home the whole time. Highly recommend this place. It is definitely in our rotation of places to stay moving forward. "
United States
Derek H.
1847 Log Home with modern comfort. Near Louisville & Bourbon Trail

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is AU$281
includes taxes & fees
11 Dec - 12 Dec
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Boulevard Stays Expansive 1BR Suite Pool, Parking & Gym

Middletown
9.8 out of 10, Exceptional, (6)
"very short a d sweet"
United States
Jessica M.
Boulevard Stays Expansive 1BR Suite Pool, Parking & Gym

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Madison
9.8 out of 10, Exceptional, (52)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is AU$381
includes taxes & fees
16 Dec - 17 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
Madison
10.0 out of 10, Exceptional, (14)
"Great little place. Location was exceptional. "
United States
Andrew P.
The price is AU$188
includes taxes & fees
16 Dec - 17 Dec
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

10 Min to Louisville, Huge Hot Tub, Awesome Backyard

Clarksville
10.0 out of 10, Exceptional, (46)
"Great location, close to lots of restaurants and shops. Clean house with a great backyard, very comfortable for our 6 adults "
United States
michael o.
10 Min to Louisville, Huge Hot Tub, Awesome Backyard

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Jeffersonville
9.4 out of 10, Exceptional, (81)
"Great location, 10-15 minute Uber ride to Louisville."
United States
William G.
The price is AU$527
includes taxes & fees
14 Dec - 15 Dec
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!

Prospect
10.0 out of 10, Exceptional, (6)
"Amazing views of the Ohio River and unique design with a lot of character. It was the perfect amount of communal space and privacy for our family of four.Only negatives were some deferred maintenance (leaking fridge, missing remotes, dirty air filter and some outdoor lights out)"
United States
David A.
The price is AU$648
includes taxes & fees
11 Dec - 12 Dec
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!

Sleeps 4, Rustic, Secluded

Lexington
8.0 out of 10, Very good, (4)
"The cabin and property were very clean and easy to find. We loved the back yard for chilling around after we got back from the event we were attending. Host was very friendly and had good communication. Will stay again if we are back in the area! "
United States
Nicole C.
The price is AU$342
includes taxes & fees
7 Jan - 8 Jan 2026
Sleeps 4, Rustic, Secluded

The Norton Commons Lavish

Louisville
10.0 out of 10, Exceptional, (9)
"Great location in a great neighborhood."
United States
Steve O.
The Norton Commons Lavish

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Madison
10.0 out of 10, Exceptional, (61)
"This was the best place I have ever stayed. The place was amazing and the hospitality exceeded expectations. I would definitely recommend staying here. "
United States
Adam K.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
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 Westport Hotel Reviews

Find out more about Westport

Everything you need to know about Westport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westport holiday rentals we have selected for you start as low as AU$188 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westport rentals

At Expedia, we put the best Westport holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Westport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Westport?

Yes, there are holiday rentals close to the most popular sights in Westport, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Westport has to offer?

Spectacular waterfront house!: This holiday home rental outside of Westport is located on a river, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Westport?

Ohio River Valley and Ohio River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Hermitage Farm and Charlestown State Park.

What are holiday rentals like in Westport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westport. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.