Default HTG hotel image

Gentryville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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.
The price is CA $153
CA $528 total
includes taxes & fees
Sep 22 - Sep 23
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
The price is CA $208
CA $548 total
includes taxes & fees
Sep 21 - Sep 22
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden interior with a television, wooden cabinets, and a plant.

3. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (73 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is CA $199
CA $240 total
includes taxes & fees
Sep 17 - Sep 18
Guest House with acreage to explore.
A wooden cabin with a porch, a picnic table, and a fire pit.

4. 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 $174
CA $318 total
includes taxes & fees
Sep 17 - Sep 18
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.

5. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (24 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is CA $208
CA $360 total
includes taxes & fees
Sep 17 - Sep 18
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

6. 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 $215
CA $367 total
includes taxes & fees
Sep 17 - Sep 18
Yellow Banks Log Cabin With Waterfront Views
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)
"Great cabin! Comfy beds."
United States
Kelly G.
The price is CA $243
CA $423 total
includes taxes & fees
Sep 20 - Sep 21
Yellow Banks Log Cabin with Lake Views
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

8. 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, (28 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is CA $138
CA $271 total
includes taxes & fees
Sep 17 - Sep 18
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A bedroom with a bunk bed, a single bed, a wooden floor, a bookshelf, and a window with curtains.

9. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
The price is CA $455
CA $675 total
includes taxes & fees
Sep 29 - Sep 30
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.

10. 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, (33 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is CA $418
CA $666 total
includes taxes & fees
Oct 1 - Oct 2
5 Miles from Holiday World sleeps 11+ —Family Escape
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, (17 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is CA $208
CA $360 total
includes taxes & fees
Sep 29 - Sep 30
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.

12. Family Style home -2 bedrooms 1 bath

Family Style home -2 bedrooms 1 bath
Birdseye
9.8 out of 10, Exceptional, (86 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 $186
CA $240 total
includes taxes & fees
Sep 17 - Sep 18
Family Style home -2 bedrooms 1 bath
A white house with green shutters, a covered porch, and a small garden.

13. Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana
Fulda
10.0 out of 10, Exceptional, (19 reviews)
"The house was wonderful! So quaint and comfortable."
United States
Samantha I.
The price is CA $294
CA $552 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Vintage House. Home in Fulda, Indiana
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

14. 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, (27 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
The price is CA $250
CA $461 total
includes taxes & fees
Sep 20 - Sep 21
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
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)
"Enjoyed the stay immensely. Very clean. Will stay again. "
United States
Mary P.
The price is CA $139
CA $542 total
includes taxes & fees
Sep 22 - Sep 23
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A single-story house with a gabled roof, white shutters, and a front porch.

16. 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)
"Very cozy and clean place! It was perfect for our group of five, including three teenagers, while we visited Holiday World. Shane is a wonderful host, and the thoughtful touches - like the selection of snacks - made us feel especially welcome. Communication was easy throughout our stay. I was also fascinated by the historical books displayed on the shelves - they were such a unique and memorable touch, adding to a very historic feel of the place and the town. "
United States
Svitlana T.
The price is CA $332
CA $506 total
includes taxes & fees
Sep 23 - Sep 24
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A two-story house with a front porch, two chairs, and a stone pillar.

17. 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 $199
CA $403 total
includes taxes & fees
Sep 23 - Sep 24
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A neatly made bed with a yellow throw blanket, white bedding, and decorative pillows. There are two bedside tables with lamps, a wall-mounted light, and two abstract paintings above the bed.

18. Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh

Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
Newburgh
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Adam B.
The price is CA $151
CA $303 total
includes taxes & fees
Sep 23 - Sep 24
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
A kitchen with white cabinets, a stainless steel refrigerator, a granite countertop, and a window with a view of greenery.

19. Cozy 2-bedroom house in Owensboro KY

Cozy 2-bedroom house in Owensboro KY
Owensboro
10.0 out of 10, Exceptional, (2 reviews)
"Great stay great host"
United States
BPCAT 0.
The price is CA $181
CA $276 total
includes taxes & fees
Sep 21 - Sep 22
Cozy 2-bedroom house in Owensboro KY
A stone fireplace with a Christmas tree and decorations, a white sofa, and a window with a view.

20. 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 $278
CA $434 total
includes taxes & fees
Sep 21 - Sep 22
Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gentryville Hotel Reviews

Sun Outdoors Lake Rudolph

Sun Outdoors Lake Rudolph

8/10 Good
"Great place for families!"
Kathleen 2-night trip
Posted 13 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, 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 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 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 Gentryville 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 Gentryville vacation rentals we have selected for you start as low as CA $240 per night. Entering your travel dates in the search wizard 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 Boyhood National Memorial 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.