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Gentryville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
3.0 star property
Gentryville
The price is CA $213
CA $560 total
includes taxes & fees
Oct 20 - Oct 21
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
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.
The price is CA $156
CA $570 total
includes taxes & fees
Oct 12 - Oct 13
The Cowboys Slumber' 2 Mi to Lincoln State Park
A bedroom with a bunk bed, a single bed, a wooden floor, a bookshelf, and a window with curtains.

3. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
"The property was perfect for our family of 4. The host was very accommodating and immediately helped us with a few minor things we needed. They are very responsive and willing to help!The kids loved the ping pong table and hangout area in the basement. They also loved having their own room. Would definitely recommend staying here!"
United States
Dustin C.
The price is CA $503
CA $782 total
includes taxes & fees
Nov 3 - Nov 4
Run Away Reindeer Retreat
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.

4. 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, (34 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is CA $384
CA $621 total
includes taxes & fees
Oct 12 - Oct 13
5 Miles from Holiday World sleeps 11+ —Family Escape
A wooden interior with a television, wooden cabinets, and a plant.

5. 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.
The price is CA $203
CA $259 total
includes taxes & fees
Oct 11 - Oct 12
Guest House with acreage to explore.
A white house with green shutters, a covered porch, and a small garden.

6. 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.
The price is CA $301
CA $564 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Vintage House. Home in Fulda, Indiana
A cozy cabin interior with a sofa, dining table, and chairs.

7. 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.
The price is CA $249
CA $435 total
includes taxes & fees
Oct 8 - Oct 9
Yellow Banks Log Cabin with Lake Views
A wooden cabin with a porch, a picnic table, and a fire pit.

8. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (35 reviews)
"We had a great time and enjoyed our stay!"
United States
Anonymous traveller
The price is CA $178
CA $342 total
includes taxes & fees
Oct 8 - Oct 9
Yellow Banks Log Cabin With Waterfront Views
A wooden gazebo with a gravel path leading to a pond, surrounded by trees and a grassy area.

9. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (24 reviews)
"Great location,very clean and cozy!"
United States
Briley E.
The price is CA $213
CA $390 total
includes taxes & fees
Oct 8 - Oct 9
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

10. 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.
The price is CA $220
CA $400 total
includes taxes & fees
Oct 11 - Oct 12
Yellow Banks Log Cabin With Waterfront Views
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

11. 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, (28 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
The price is CA $256
CA $468 total
includes taxes & fees
Oct 12 - Oct 13
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
A single-story house with a gabled roof, white shutters, and a front porch.

12. 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.
The price is CA $340
CA $520 total
includes taxes & fees
Oct 12 - Oct 13
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

13. 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, (29 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.
The price is CA $141
CA $277 total
includes taxes & fees
Oct 11 - Oct 12
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A two-story house with a front porch, two chairs, and a stone pillar.

14. 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 attentive host. Good value. This house was perfect for our group's trip to Holiday World. We're looking at staying again in the future."
United States
Patricia G.
The price is CA $203
CA $411 total
includes taxes & fees
Oct 12 - Oct 13
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

15. 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.
The price is CA $166
CA $585 total
includes taxes & fees
Oct 13 - Oct 14
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

16. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (17 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is CA $213
CA $390 total
includes taxes & fees
Oct 8 - Oct 9
Yellow Banks Log Cabin With Waterfront Views
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, (89 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
The price is CA $228
CA $288 total
includes taxes & fees
Oct 8 - Oct 9
Family Style home -2 bedrooms 1 bath
A stone fireplace with a Christmas tree and decorations, a white sofa, and a window with a view.

18. 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.
The price is CA $284
CA $446 total
includes taxes & fees
Oct 13 - Oct 14
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.

19. 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.
The price is CA $255
CA $376 total
includes taxes & fees
Oct 12 - Oct 13
The Blue Herron of Carpenters Lake
A clear view of a swimming pool with a stone-lined edge and a wooden deck area in the background.

20. 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, (23 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.
The price is CA $127
CA $225 total
includes taxes & fees
Oct 11 - Oct 12
MILSuite separate entry...close to all things Owensboro and Daviess County.
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

Santas Lodge and Resort

Santas Lodge and Resort

10/10 Excellent
"Clean room Breakfast was good Swimming pool and hot tube nice Friendly helpful staff Would stay again"
Jennifer 1-night trip
Posted 1 day ago
Santas Lodge and Resort

Find out more about Gentryville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gentryville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.