Westport Vacation Rentals

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Oct 1 - Oct 2
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Vacation Rentals in Westport

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (40)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
$194 nightly
The price is $223
Oct 22 - Oct 23
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Interior

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

9.8 out of 10, Exceptional, (72)
"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! "
$1,112 nightly
The price is $1,291
Oct 12 - Oct 13
Total with taxes and fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
10 Min to Louisville, Huge Hot Tub, Awesome Backyard
Terrace/patio

10 Min to Louisville, Huge Hot Tub, Awesome Backyard

10.0 out of 10, Exceptional, (42)
"It was a very quiet community and a great place to stay if you enjoy the quiet and peacefulness have everything you would need in the house to make your stay comfortable And the closeness two stores was a plus for the little things you would need"
10 Min to Louisville, Huge Hot Tub, Awesome Backyard
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (12)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
$146 nightly
The price is $168
Oct 2 - Oct 3
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Outdoor dining

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!"
$273 nightly
The price is $317
Oct 5 - Oct 6
Total with taxes and fees
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior

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

10.0 out of 10, Exceptional, (52)
"Great property, great location, and amazing hosts. Incredible attention to detail and service. It would take too long to describe everything that impressed us so I'll just say it's all perfect and if this place is available when you're visiting Madison, stop searching and just book it."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (19)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
Charming 3-bedroom house in lovely downtown Madison.
Exterior

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
8.4 out of 10, Very Good, (5)
Charming 3-bedroom house in lovely downtown Madison.
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Outdoor spa tub

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

9.8 out of 10, Exceptional, (19)
"Great place good time "
$639 nightly
The price is $742
Oct 2 - Oct 3
Total with taxes and fees
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Relaxing Country Getaway
Interior

Relaxing Country Getaway

9.4 out of 10, Exceptional, (40)
"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
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn
Outdoor spa tub

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

10.0 out of 10, Exceptional, (10)
"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."
$280 nightly
The price is $322
Oct 8 - Oct 9
Total with taxes and fees
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Fridge, microwave, oven, stovetop

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

10.0 out of 10, Exceptional, (9)
"Was the perfect little overnight stay! "
$140 nightly
The price is $158
Oct 26 - Oct 27
Total with taxes and fees
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
5BR Very Spacious Home! Perfect for Family!
Fridge, microwave, oven, stovetop

5BR Very Spacious Home! Perfect for Family!

9.2 out of 10, Wonderful, (17)
"My company stayed here during a work trip and we liked it so much we extended our stay. Great area with lots to do!"
$496 nightly
The price is $521
Oct 28 - Oct 29
Total with taxes and fees
5BR Very Spacious Home! Perfect for Family!
Cozy Tree-Lined Carriage Home - Stay in Serenity!
Exterior

Cozy Tree-Lined Carriage Home - Stay in Serenity!

9.6 out of 10, Exceptional, (15)
"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. "
$150 nightly
The price is $174
Oct 13 - Oct 14
Total with taxes and fees
Cozy Tree-Lined Carriage Home - Stay in Serenity!
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed our time there, and the little extra touches were a pleasant surprise! The house was incredibly clean and the owner was very prompt and responsive to questions we had. Definitely would stay again!"
$323 nightly
The price is $371
Oct 15 - Oct 16
Total with taxes and fees
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (3)
"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)"
$389 nightly
The price is $452
Oct 2 - Oct 3
Total with taxes and fees
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!
Historic city overlook suite 206, Historic city overlook suite 306
1 bedroom

Historic city overlook suite 206, Historic city overlook suite 306

9.4 out of 10, Exceptional, (8)
"Very clean and cozy! Nice area close to town. "
$169 nightly
The price is $180
Oct 8 - Oct 9
Total with taxes and fees
Historic city overlook suite 206, Historic city overlook suite 306
Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Property grounds

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
The Norton Commons Luxe
Interior

The Norton Commons Luxe

10.0 out of 10, Exceptional, (37)
"Great neighborhood and walkable to several nearby restaurants. Had a great stay!"
The Norton Commons Luxe
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
Exterior

Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

9.0 out of 10, Wonderful, (6)
"Would definitely stay here again."
$228 nightly
The price is $264
Oct 2 - Oct 3
Total with taxes and fees
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
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

Comfort Inn & Suites Clarksville - Louisville North

Comfort Inn & Suites Clarksville - Louisville North

10/10 Excellent
"Very clean and the bathroom is unique"
Shawna 1-night trip
Posted 3 days ago
Comfort Inn & Suites Clarksville - Louisville North

Find out more about Westport

Find out more about Westport

Everything you need to know about Westport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westport vacation 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 low season months. For more hustle and bustle, you may prefer to visit Westport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westport rentals

At Expedia, we put the best Westport vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Westport?

Yes, there are vacation rentals near the most popular attractions in Westport, or you can choose a more secluded option if you're looking for relaxation.

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

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville: This vacation home rental near Westport is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

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 larger area, you’ll find Hermitage Farm and Charlestown State Park.

What are vacation rentals like in Westport?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Westport. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.