Westport Holiday Rentals

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Holiday Rentals in Westport

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
"Great old home and cool neighborhood. "
Charming 3-bedroom house in lovely downtown Madison.

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

10.0 out of 10, Exceptional, (3)
"A wonderful place to host a large family. The number of rooms and spaces made it very comfortable for our family to have time together in a great home setting. The extra bonus room out back was a wonderful surprise, where we could all hang out together nightly. We would definitely return. "
Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

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

9.8 out of 10, Exceptional, (71)
"This place was a perfect stay for my bachelor party! There was a ton of room, the host was very responsive with any questions and it had everything we needed. Highly recommend! "
The price is AU$2,040
includes taxes & fees
29 Sept - 30 Sept
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

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

10.0 out of 10, Exceptional, (47)
"Everything was really great...the property is beautiful...the amenities were amazing...and the owners so sweet and caring...the would answer a text message pronto...will stay again!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

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

10.0 out of 10, Exceptional, (179)
"Way beyond our expectations. We loved our stay!"
The price is AU$565
includes taxes & fees
8 Sept - 9 Sept
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

Cozy Tree-Lined Carriage Home - Stay in Serenity!

9.6 out of 10, Exceptional, (14)
"We absolutely loved staying here while in town visiting family. This place is spacious and beautifully decorated with lots of amenities. We would definitely stay here again. "
The price is AU$255
includes taxes & fees
15 Sept - 16 Sept
Cozy Tree-Lined Carriage Home - Stay in Serenity!

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

9.8 out of 10, Exceptional, (39)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is AU$355
includes taxes & fees
7 Sept - 8 Sept
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Spectacular waterfront house!

9.6 out of 10, Exceptional, (78)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!

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

2.0 star property
9.8 out of 10, Exceptional, (9)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is AU$175
includes taxes & fees
9 Sept - 10 Sept
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

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

9.6 out of 10, Exceptional, (74)
"Great location, 10-15 minute Uber ride to Louisville."
The price is AU$538
includes taxes & fees
8 Sept - 9 Sept
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Relaxing Country Getaway

9.4 out of 10, Exceptional, (36)
"It was a very nice little get away without going too far. Everything was clean, including the hot tub. We will definitely keep this place in mind in the future!"
Relaxing Country Getaway

Sunset over the city Suite 201, Sunset over the city Suite 201

9.6 out of 10, Exceptional, (9)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is AU$239
includes taxes & fees
7 Oct - 8 Oct
Sunset over the city Suite 201, Sunset over the city Suite 201

Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn

10.0 out of 10, Exceptional, (7)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
The price is AU$533
includes taxes & fees
20 Sept - 21 Sept
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn

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

10.0 out of 10, Exceptional, (2)
"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)"
The price is AU$761
includes taxes & fees
7 Sept - 8 Sept
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!

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

10.0 out of 10, Exceptional, (8)
"Clean, spacious, nicely decorated, comfortable bed. For us it was also nostalgic - from the windows on Main we could see the home where my husband’s mother was raised and the location of his grandparents’ grocery (in the latter 1930s- 1971).. now the Attic, a coffee, pastry, sandwich shop. "
The price is AU$353
includes taxes & fees
17 Sept - 18 Sept
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

4 rooms for rent

2.0 out of 10, (1)
"We ended up not staying due to not being able to get a hold of the host. Also called vrbo and they couldnt contact the host"
The price is AU$215
includes taxes & fees
15 Sept - 16 Sept
4 rooms for rent

Modern Nature Cabin | Private Escape in the Forest

9.4 out of 10, Exceptional, (3)
"Very nice place, the hike to the falls was pretty neat as well. Close to everything, yet still secluded. "
The price is AU$445
includes taxes & fees
1 Oct - 2 Oct
Modern Nature Cabin | Private Escape in the Forest

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The price is AU$726
includes taxes & fees
12 Sept - 13 Sept
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Bungalow on Main!!

9.8 out of 10, Exceptional, (18)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!

Peaceful getaway centrally located just min. from Madison and Belterra casino.

9.4 out of 10, Exceptional, (26)
"We enjoyed our stay and would recommend to others."
Peaceful getaway centrally located just min. from Madison and Belterra casino.
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

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$175 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?

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!: This holiday home rental outside of Westport is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Westport?

Explore the area and family-friendly sights such as IceLand Sports Complex, or get out into nature at a spot like Ohio River. 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.