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Gentryville 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 Gentryville vacation rentals

A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

1. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (1 review)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
$360 nightly
The price is $403
Oct 19 - Oct 20
Total with taxes and fees
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

2. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
$352 nightly
The price is $394
Oct 19 - Oct 20
Total with taxes and fees
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden cabin with a porch, a picnic table, and a fire pit.

3. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (37 reviews)
"Very happy with our stay here. The cabin was clean, the beds were comfortable, and the owners were very easy to communicate with. We would definitely stay here again."
United States
Cyndi L.
$216 nightly
The price is $242
Oct 19 - Oct 20
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
A wooden interior with a television, wooden cabinets, and a plant.

4. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"Doug is a wonderful host who goes the extra mile to make sure you are comfortable and enjoy your stay. His property is amazing, clean, and quiet. This was our third stay and we will definitely be back again and again."
United States
tasha k.
$163 nightly
The price is $183
Oct 19 - Oct 20
Total with taxes and fees
Guest House with acreage to explore.
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

5. Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Huntingburg
9.8 out of 10, Exceptional, (30 reviews)
"Me and my family stayed while visiting holiday world and we highly recommend. Prices was affordable and the host was great."
United States
James B.
$174 nightly
The price is $195
Oct 19 - Oct 20
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A wooden gazebo with a gravel path leading to a pond, surrounded by trees and a grassy area.

6. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (25 reviews)
"Great location,very clean and cozy!"
United States
Briley E.
$245 nightly
The price is $274
Oct 19 - Oct 20
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

7. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.8 out of 10, Exceptional, (8 reviews)
"This was a quiet, clean, and convenient little cabin close to Holiday World which is what we stayed for. "
United States
Ashley J.
$251 nightly
The price is $281
Oct 19 - Oct 20
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
A cozy cabin interior with a sofa, dining table, and chairs.

8. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"A nice little cabin for our trip to holiday world."
United States
Brandon R.
$273 nightly
The price is $306
Oct 19 - Oct 20
Total with taxes and fees
Yellow Banks Log Cabin with Lake Views
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

9. Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
$346 nightly
The price is $387
Oct 19 - Oct 20
Total with taxes and fees
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A clear view of a swimming pool with a stone-lined edge and a wooden deck area in the background.

10. MILSuite separate entry...close to all things Owensboro and Daviess County.

MILSuite separate entry...close to all things Owensboro and Daviess County.
Owensboro
9.8 out of 10, Exceptional, (24 reviews)
"Second time staying at this location, both times have been exactly what I needed while in Owensboro. Attentive host and clean and tidy location equals a great and reasonably priced stay. Highly recommend for single travelers or couples looking for a place in Owensboro!"
United States
Randy W.
$139 nightly
The price is $158
Oct 19 - Oct 20
Total with taxes and fees
MILSuite separate entry...close to all things Owensboro and Daviess County.
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

11. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (18 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
$245 nightly
The price is $274
Oct 19 - Oct 20
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
A white house with green shutters, a covered porch, and a small garden.

12. Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana
Fulda
10.0 out of 10, Exceptional, (20 reviews)
"The house is just as described on the website. It is within 10 minutes to Holiday world, the beds were very comfortable. Excellent water pressure. The only complaint is there’s very little cell service in the area. I would definitely rent this place again."
United States
Penny F.
$355 nightly
The price is $397
Oct 19 - Oct 20
Total with taxes and fees
Cozy Vintage House. Home in Fulda, Indiana
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

13. Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.

Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
Evanston
10.0 out of 10, Exceptional, (29 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
$296 nightly
The price is $332
Oct 19 - Oct 20
Total with taxes and fees
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
A compact kitchen with wooden cabinets, a stainless steel refrigerator, an oven, a microwave, a sink, and a kettle. There is a dining table with chairs.

14. 5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.8 out of 10, Exceptional, (35 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
$369 nightly
The price is $413
Nov 1 - Nov 2
Total with taxes and fees
5 Miles from Holiday World sleeps 11+ —Family Escape
A bedroom with a bunk bed, a single bed, a wooden floor, a bookshelf, and a window with curtains.

15. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
"We loved and enjoyed our stay here! The outdoor space is beautiful and peaceful. The inside was so well planned out with lots of cute tiny touches that made it feel so welcoming! We will definitely be returning!"
United States
Marie C.
$493 nightly
The price is $541
Nov 18 - Nov 19
Total with taxes and fees
Run Away Reindeer Retreat
A two-story house with a front porch, two chairs, and a stone pillar.

16. THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Lynnville
9.8 out of 10, Exceptional, (16 reviews)
"Very cool old house but clean and tidy everything was great"
United States
Robert Y.
$260 nightly
The price is $291
Oct 19 - Oct 20
Total with taxes and fees
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A building with a green and beige exterior, a front porch with chairs and a fire pit, and two large garage doors.

17. Family Style home -2 bedrooms 1 bath

Family Style home -2 bedrooms 1 bath
Birdseye
9.8 out of 10, Exceptional, (90 reviews)
"Great place to stay not far from the lake the hosts were amazing lots of room and very nice place and very fair price 100% would stay again!!"
United States
Kristina
$183 nightly
The price is $205
Oct 19 - Oct 20
Total with taxes and fees
Family Style home -2 bedrooms 1 bath
A single-story house with a gabled roof, white shutters, and a front porch.

18. 3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Ferdinand
10.0 out of 10, Exceptional, (4 reviews)
"The property was conveniently located within all of our planned attractions."
United States
Lavar B.
$329 nightly
The price is $368
Oct 19 - Oct 20
Total with taxes and fees
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A stone fireplace with a Christmas tree and decorations, a white sofa, and a window with a view.

19. Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path

Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
Lewisport
10.0 out of 10, Exceptional, (2 reviews)
"What a great place to stay to get away from it all with the family! "
United States
Favour R.
$286 nightly
The price is $315
Oct 19 - Oct 20
Total with taxes and fees
Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
A modern kitchen with a TV, bar stools, and a trash can.

20. The Blue Herron of Carpenters Lake

The Blue Herron of Carpenters Lake
Maceo
8.4 out of 10, Very good, (5 reviews)
"Very clean, they had everything you could possibly need to start, the complementary items was a nice gesture, love my cup of coffee looking at the lake, my kids love it they didn't want to leave, very beautiful home for a weekend getaway recommended 100% we enjoyed our stay."
United States
Stephanie A.
$232 nightly
The price is $263
Oct 19 - Oct 20
Total with taxes and fees
The Blue Herron of Carpenters Lake
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 Gentryville Hotel Reviews

Sun Outdoors Lake Rudolph

Sun Outdoors Lake Rudolph

10/10 Excellent
"So much fun!"
Annabell 3-night trip
Posted 3 hours ago
Sun Outdoors Lake Rudolph

Find out more about Gentryville

Everything you need to know about Gentryville 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 Gentryville 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 Gentryville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gentryville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gentryville. 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 Gentryville 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 Gentryville rentals

At Expedia, we put the best Gentryville 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 Gentryville 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 Gentryville 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 Gentryville. 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

Are there vacation rentals in Gentryville?

Yes, we have vacation rentals near popular attractions in Gentryville, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Gentryville?

The Cowboys Slumber' 2 Mi to Lincoln State Park: Visitors like this Gentryville vacation home rental. It offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Our travelers also rate The Family Oasis just 6 miles from Holiday World as a favorite home for rent in Gentryville.

How many vacation rentals are there in Gentryville?

Expedia has 3 vacation rentals for your stay in Gentryville.

What can I see and do in Gentryville?

While exploring the area, visit family-friendly sights like Holiday World and Splashin' Safari, or get outside and enjoy nature at Lincoln State Park. Colonel William Jones Home and Lincoln Amphitheatre are a couple of places you'll find in the larger area.

What are vacation rentals like in Gentryville?

Vacation rentals are privately owned properties you can book for a couple days or more in Gentryville. Vacation rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a small group gathering.