Search Vacation Homes in Westport

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Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Westport vacation homes

Terrace/patio
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Pendleton
9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
$205 nightly
The price is $226
Jan 4 - Jan 5, 2026
Total with taxes and fees
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Exterior
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

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

Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
St. Matthews
9.0 out of 10, Wonderful, (6)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
$230 nightly
The price is $266
Dec 14 - Dec 15
Total with taxes and fees
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
Fridge, microwave, oven, stovetop
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
$130 nightly
The price is $147
Dec 14 - Dec 15
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Interior
Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (47)
"Located near lovely parks on the river. There is very little traffic in this area, yet you are close to downtown.We've stayed here twice because it is so clean, comfortable, stylish, and relaxing. "
United States
Debbie B.
Carriage House, 7 minutes from downtown Louisville
Interior
Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
$394 nightly
The price is $445
Dec 14 - Dec 15
Total with taxes and fees
Emerald Lake Retreat Charlestown
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
$196 nightly
The price is $225
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Artist’s A-Frame
Family House, Multiple Beds | Private kitchen | Fridge, microwave, oven, stovetop
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
4.0 star property
Sellersburg
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
United States
Tammy
$334 nightly
The price is $352
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
Property grounds
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
Jeffersonville
9.6 out of 10, Exceptional, (15)
"The property was very nice for our family getaway, would book again."
United States
Roberta
$254 nightly
The price is $287
Jan 12 - Jan 13, 2026
Total with taxes and fees
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
Exterior
Sleeps 4, Rustic, Secluded

Sleeps 4, Rustic, Secluded

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.
$214 nightly
The price is $218
Dec 17 - Dec 18
Total with taxes and fees
Sleeps 4, Rustic, Secluded
Interior
Stylish Jeffersonville Home - Mins from Louisville

Stylish Jeffersonville Home - Mins from Louisville

Stylish Jeffersonville Home - Mins from Louisville
Jeffersonville
9.0 out of 10, Wonderful, (20)
"This was a great place for us to stay for an event at the expedition center. Close to the highway for quick access to the city. "
United States
Chad L.
$281 nightly
The price is $317
Jan 7 - Jan 8, 2026
Total with taxes and fees
Stylish Jeffersonville Home - Mins from Louisville
Exterior detail
✪Heated Pool, Firepit, Bikes, Grill, Pets✪

✪Heated Pool, Firepit, Bikes, Grill, Pets✪

✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Jeffersonville
8.6 out of 10, Excellent, (20)
"Nice older home. Pool is small, but was still nice to use with the heat. Tyler fantastic to work with, very responsive, even added a hot tub amenity which wasn’t in initial listing. "
United States
Ken H.
$293 nightly
The price is $335
Dec 14 - Dec 15
Total with taxes and fees
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Smart TV
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (53)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
$217 nightly
The price is $250
Dec 16 - Dec 17
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Lobby
Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest
Hanover
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
$175 nightly
The price is $185
Dec 21 - Dec 22
Total with taxes and fees
Modern Nature Cabin | Private Escape in the Forest
Smart TV
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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
9.8 out of 10, Exceptional, (34)
"Great place to stay for Hanover college "
United States
Lindsey M.
$233 nightly
The price is $268
Dec 28 - Dec 29
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Terrace/patio
Charming house, sleeps plenty with Hot Tub and large backyard and fire pit

Charming house, sleeps plenty with Hot Tub and large backyard and fire pit

Charming house, sleeps plenty with Hot Tub and large backyard and fire pit
Jeffersonville
9.0 out of 10, Wonderful, (2)
"House was perfect location for our plans. Everything was close and convenient"
United States
Josh M.
$236 nightly
The price is $267
Dec 15 - Dec 16
Total with taxes and fees
Charming house, sleeps plenty with Hot Tub and large backyard and fire pit
TV, offices
4BR Cozy Home Near Distilleries & Historic Sites!

4BR Cozy Home Near Distilleries & Historic Sites!

4BR Cozy Home Near Distilleries & Historic Sites!
2.0 star property
Brownsboro Zorn
10.0 out of 10, Exceptional, (1)
"Perfect house and perfect location. We have a big family and needed more space than a hotel. Great location close to our family and every thing you want to do in Louisville!"
United States
Chas R.
$343 nightly
The price is $369
Dec 21 - Dec 22
Total with taxes and fees
4BR Cozy Home Near Distilleries & Historic Sites!
Sauna
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

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

+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.
$274 nightly
The price is $313
Dec 14 - Dec 15
Total with taxes and fees
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

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

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Madison
10.0 out of 10, Exceptional, (14)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
$313 nightly
The price is $360
Dec 14 - Dec 15
Total with taxes and fees
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop
12 Mins To Louisville, Gameroom, Patio&Grill, Fenced Yard

12 Mins To Louisville, Gameroom, Patio&Grill, Fenced Yard

12 Mins To Louisville, Gameroom, Patio&Grill, Fenced Yard
Jeffersonville
8.8 out of 10, Excellent, (3)
"Check in was very easy. "
United States
Kelly S.
$335 nightly
The price is $379
Dec 14 - Dec 15
Total with taxes and fees
12 Mins To Louisville, Gameroom, Patio&Grill, Fenced Yard
Exterior detail
The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
2.0 star property
La Grange
10.0 out of 10, Exceptional, (5)
"Clean, remarkably spacious and within walking distance of the historic downtown, that's for starters. My Spouse and I had weekend business in Louisville and Lagrange is just a short hop down the road, but with less traffic, another plus. We highly recommend."
United States
Edward C.
$283 nightly
The price is $321
Jan 5 - Jan 6, 2026
Total with taxes and fees
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

Microtel Inn by Wyndham Louisville East

Microtel Inn by Wyndham Louisville East

10/10 Excellent
"I stayed for 2 nights. The room was reasonably priced. It was nice and clean. It even had a window seat. Check in and out was quick and easy with friendly staff. The location was very convinient (only 2 minutes from work). I would definitely stay there again. The only problems I had was the TV remote was very worn and hard to change stations and the handycap shower head would not stay in the top position, so it was a challenge to wash my hair. I also would request clean towels for the next day."
Tracey 2-night trip
Posted 1 day ago
Microtel Inn by Wyndham Louisville East

Find out more about Westport

Westport Vacation Homes information

Number of reviews
398
Accommodation
297 Vacation Homes
Lowest Price
$147
Highest Price
$445

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