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Westport Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Westport vacation rentals

A multi-story hotel with a flat facade, a parking lot in front, and a sign indicating 'STUDIOS.'

1. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (12 reviews)
"The front desk staff made check in/out so smooth & were amazing!"
United States
Brandon
The price is CA $126
CA $157 total
includes taxes & fees
Oct 24 - Oct 25
StudioRes by Marriott Louisville East
A house with a large garage, a dock, and a river.

2. River Retreat

River Retreat
Charlestown
10.0 out of 10, Exceptional, (1 review)
"Easy check in. Nice cozy home right by the river. Even left a golf cart for use when staying!"
United States
Brady S.
The price is CA $175
CA $406 total
includes taxes & fees
Oct 21 - Oct 22
River Retreat
A rectangular swimming pool with lounge chairs and umbrellas, surrounded by lush greenery and a gazebo.

3. Exclusive Farmhouse w/ a Romantic Garden View!

Exclusive Farmhouse w/ a Romantic Garden View!
Prospect
10.0 out of 10, Exceptional, (1 review)
"Scenic horse farm. Secluded, private, and quiet. I couldn't be happier with the accommodations. Would like to return when in the area."
United States
Darlene N.
The price is CA $95
CA $299 total
includes taxes & fees
Oct 26 - Oct 27
Exclusive Farmhouse w/ a Romantic Garden View!
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

4. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (26 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
The price is CA $153
CA $229 total
includes taxes & fees
Oct 26 - Oct 27
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

5. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is CA $102
CA $301 total
includes taxes & fees
Oct 25 - Oct 26
Modern cabin very close to scenic riverfront walks
A modern hotel with a 'Stay Apt Suites' sign, featuring a brick facade, large windows, and a parking lot.

6. stayAPT Suites Louisville North-Clarksville

stayAPT Suites Louisville North-Clarksville
4.0 star property
Clarksville
9.8 out of 10, Exceptional, (57 reviews)
"Great option for a long term stay, good area many businesses in walking distance!"
Canada
Darlene
The price is CA $196
CA $221 total
includes taxes & fees
Oct 30 - Oct 31
stayAPT Suites Louisville North-Clarksville
A house with a fire pit and Adirondack chairs in the yard.

7. Exclusive Buckner retreat w/ theater & game room!

Exclusive Buckner retreat w/ theater & game room!
Buckner
6.0 out of 10, (1 review)
"The house was big enough for my family of 6. The yard was great for my children to run around and for us to sit around the fire at night. The theater room was nice for my children to hang out in. The game room was nice to play pool in but unfortunately the darts for the dart board were in sad shape so we couldn't utilize that. The home gym was nice to workout in. Unfortunately we walked into ants all over the kitchen pantry and on the counters. We contacted the host (company) right away and they...
United States
Jenn M.
The price is CA $156
CA $562 total
includes taxes & fees
Oct 25 - Oct 26
Exclusive Buckner retreat w/ theater & game room!
A compact kitchen with a refrigerator, microwave, stove, and sink. There is a dining table with chairs and a patterned rug.

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

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Memphis
10.0 out of 10, Exceptional, (28 reviews)
"Great host and a great location!"
United States
P a.
The price is CA $140
CA $238 total
includes taxes & fees
Oct 29 - Oct 30
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Property grounds

9. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is CA $126
CA $242 total
includes taxes & fees
Oct 19 - Oct 20
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

10. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is CA $87
CA $168 total
includes taxes & fees
Oct 19 - Oct 20
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A living room with a ceiling fan, a sofa, a coffee table, and a wooden cabinet.

11. Mins to Louisville•Big Four Bridge•Down Town•2024 Build•Fire pit•Ping Pong

Mins to Louisville•Big Four Bridge•Down Town•2024 Build•Fire pit•Ping Pong
Jeffersonville
10.0 out of 10, Exceptional, (2 reviews)
"Excellent stay! Everything was clean and well furnished. The bed was so comfortable and shutters helped the room stay dark so we slept great. The neighborhood is lovely and we enjoyed taking an evening walk down to the pond. Close to stores and restaurants and everything we needed. Would recommend 100%"
United States
Andrea G.
The price is CA $115
CA $292 total
includes taxes & fees
Oct 19 - Oct 20
Mins to Louisville•Big Four Bridge•Down Town•2024 Build•Fire pit•Ping Pong
A swimming pool with lounge chairs and a building in the background.

12. Boulevard Stays - Hurstbourne

Boulevard Stays - Hurstbourne
3.0 star property
Middletown
The price is CA $166
CA $336 total
includes taxes & fees
Oct 19 - Oct 20
Boulevard Stays - Hurstbourne
A covered deck with a sectional sofa, a table, and a sliding glass door leading to an interior living area with a couch and a rug.

13. Relaxing stay near Louisville's top attractions!

Relaxing stay near Louisville's top attractions!
Louisville
10.0 out of 10, Exceptional, (1 review)
"Great property. A calm, peaceful haven inside the city."
United States
David L.
The price is CA $96
CA $328 total
includes taxes & fees
Oct 29 - Oct 30
Relaxing stay near Louisville's top attractions!
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

14. The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (54 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is CA $185
CA $378 total
includes taxes & fees
Oct 22 - Oct 23
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A bedroom with a bed, a bedside lamp, a window with blinds, a wooden closet, and a ceiling fan.

15. Exclusive one-story retreat close to attractions!

Exclusive one-story retreat close to attractions!
Rockcreek Lexington Road
The price is CA $86
CA $315 total
includes taxes & fees
Nov 2 - Nov 3
Exclusive one-story retreat close to attractions!
A hotel room with a bed, a desk, a chair, a ceiling fan, a door, a mirror, and a framed picture on the wall.

16. Riverstone Retreat | Ohio River Views + Hot Tub

Riverstone Retreat | Ohio River Views + Hot Tub
Prospect
The price is CA $232
CA $672 total
includes taxes & fees
Nov 2 - Nov 3
Riverstone Retreat | Ohio River Views + Hot Tub
A rooftop terrace with four wicker chairs, a wooden deck, and a brick wall.

17. Cheeky RxR | Art Museum Loft with rooftop deck!

Cheeky RxR | Art Museum Loft with rooftop deck!
La Grange
The price is CA $276
CA $604 total
includes taxes & fees
Nov 3 - Nov 4
Cheeky RxR | Art Museum Loft with rooftop deck!
A room with a bed, two armchairs, a small table, and a microwave.

18. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is CA $198
CA $453 total
includes taxes & fees
Oct 19 - Oct 20
Lakeside Cottage: 1 bed/1 bath
An outdoor patio with wicker furniture, a stone fire pit, and a pergola.

19. Great Location! Comfortable Studio Suite | Pool Access

Great Location! Comfortable Studio Suite | Pool Access
Middletown
9.6 out of 10, Exceptional, (4 reviews)
"Unit was equipped with a small kitchenette- but great breakfast was served in common area on first floor, including egg/potato sausage and biscuits and gravy. Fruit cereal and juices available, in addition to coffee. Staff worked hard to make sure things were well stocked. The room was comfortable and shower was good!"
United States
Christine T.
The price is CA $162
CA $223 total
includes taxes & fees
Oct 25 - Oct 26
Great Location! Comfortable Studio Suite | Pool Access
A wooden deck with a green door, wicker chairs, and a small table.

20. The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (7 reviews)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
The price is CA $380
CA $658 total
includes taxes & fees
Nov 1 - Nov 2
The Sweet Retreat Wheelchair Accessible Historic Home
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

Clarion Pointe Louisville East

Clarion Pointe Louisville East

10/10 Excellent
"Facilities were superb. Check in went well and room was great. Stayed as a family weekend event. Breakfast was great. The coffee was what coffee should be, flavorful and strong, not slughtly brown hot water."
Lene 1-night trip
Posted 13 hours ago
Clarion Pointe Louisville East

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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westport vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westport vacation rentals we have selected for you start as low as CA $157 per night. Entering your travel dates in the search wizard 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. 

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?

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+: This vacation home rental near Westport offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

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 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.