Gentryville Vacation Rentals

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Vacation Rentals in Gentryville

Fridge, microwave, oven, stovetop
Tranquil Hideaway: Your Private Lakefront Retreat

Tranquil Hideaway: Your Private Lakefront Retreat

Dale
9.4 out of 10, Exceptional, (13)
"This property is amazing! We loved the privacy and peacefulness. The house is great and we will definitely be coming back!"
United States
Natalie S.
$243 nightly
The price is $266
Dec 9 - Dec 10
Total with taxes and fees
Tranquil Hideaway: Your Private Lakefront Retreat
Fridge, microwave, oven, stovetop
Barn in the Burgh

Barn in the Burgh

Newburgh
10.0 out of 10, Exceptional, (11)
"Beautiful warm cozy place. We stayed due to a funeral and it is the perfect place wind down and relax. Planning to come back again! "
United States
Rebecca P.
$297 nightly
The price is $325
Dec 9 - Dec 10
Total with taxes and fees
Barn in the Burgh
Fridge, microwave, oven, stovetop
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, (20)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
$175 nightly
The price is $196
Dec 9 - Dec 10
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Smart TV
Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views

Dale
9.6 out of 10, Exceptional, (20)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
$217 nightly
The price is $238
Dec 9 - Dec 10
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
3 bedrooms, desk, iron/ironing board, travel crib
Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana

Fulda
9.8 out of 10, Exceptional, (6)
"Wonderful experience! Easy to book, full of charm, clean, comfy, and close to Holiday World. Very family friendly with toys/games provided. Will definitely be booking to stay again!"
United States
Kristin A.
$280 nightly
The price is $314
Dec 14 - Dec 15
Total with taxes and fees
Cozy Vintage House. Home in Fulda, Indiana
1 bedroom, free WiFi, bed sheets
Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views

Dale
10.0 out of 10, Exceptional, (17)
"Great setting, good beds, and clean!"
United States
Doug W.
$217 nightly
The price is $238
Dec 9 - Dec 10
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Dining
Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views

Dale
8.8 out of 10, Excellent, (19)
"The cabin was a cozy place to stay and close enough to holiday world without the headache of keeping my younger kids silent like I would have if we stayed in a hotel! Very clean and organized! "
United States
Ashley J.
$241 nightly
The price is $264
Dec 9 - Dec 10
Total with taxes and fees
Yellow Banks Log Cabin with Lake Views
Interior
Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views

Dale
10.0 out of 10, Exceptional, (7)
"This was a quiet, clean, and convenient little cabin close to Holiday World which is what we stayed for. "
United States
Ashley J.
$252 nightly
The price is $276
Dec 9 - Dec 10
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Fridge, microwave, oven, stovetop
5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape

Dale
9.4 out of 10, Exceptional, (12)
"Absolutely amazing host, they made the check in process so easy. It was minutes from Holiday World so it made our trip so well worth it. The house was beautiful and the game room was the favorite part of the kid’s night. "
United States
Sabrina S.
$343 nightly
The price is $384
Dec 9 - Dec 10
Total with taxes and fees
5 Miles from Holiday World sleeps 11+ —Family Escape
Smart TV, fireplace, video games, DVD player
Family Style home -2 bedrooms 1 bath

Family Style home -2 bedrooms 1 bath

Birdseye
10.0 out of 10, Exceptional, (76)
"Friendly hosts, very clean, quiet, and definitely more comfortable than a hotel room. "
United States
Jason
$201 nightly
The price is $225
Dec 9 - Dec 10
Total with taxes and fees
Family Style home -2 bedrooms 1 bath
Pool
MILSuite separate entry...close to all things Owensboro and Daviess County.

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

2.0 star property
Owensboro
9.8 out of 10, Exceptional, (21)
"We loved our stay here! The property was super clean!"
United States
Meredith B.
$155 nightly
The price is $176
Dec 31 - Jan 1, 2026
Total with taxes and fees
MILSuite separate entry...close to all things Owensboro and Daviess County.
Exterior
💦 Doe Ridge – Hilltop Country Home with Hot Tub ➠ 2049

💦 Doe Ridge – Hilltop Country Home with Hot Tub ➠ 2049

2.0 star property
Lewisport
$601 nightly
The price is $657
Dec 21 - Dec 22
Total with taxes and fees
💦 Doe Ridge – Hilltop Country Home with Hot Tub ➠ 2049
Property grounds
Guest House with acreage to explore.

Guest House with acreage to explore.

Tennyson
9.6 out of 10, Exceptional, (60)
"We enjoyed the property and Doug was a welcoming host. "
United States
Bess C.
$145 nightly
The price is $159
Dec 9 - Dec 10
Total with taxes and fees
Guest House with acreage to explore.
Fridge, microwave, oven, stovetop
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh

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

Newburgh
$152 nightly
The price is $170
Dec 14 - Dec 15
Total with taxes and fees
Cypress Suites 9A - KING 2BD/1BA Apt in Newburgh
Property grounds
Lakeside Cabin Near Holiday World Perfect for Families & Friends

Lakeside Cabin Near Holiday World Perfect for Families & Friends

Troy
10.0 out of 10, Exceptional, (50)
"Thanks for sharing your beautiful home!"
United States
Megan’s A.
$492 nightly
The price is $551
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lakeside Cabin Near Holiday World Perfect for Families & Friends
Interior
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

2.0 star property
Lewisport
$279 nightly
The price is $308
Dec 9 - Dec 10
Total with taxes and fees
Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
Property grounds
Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views

Dale
9.2 out of 10, Wonderful, (13)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
$217 nightly
The price is $238
Dec 9 - Dec 10
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
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

Fairfield Inn & Suites Jasper

Fairfield Inn & Suites Jasper

10/10 Excellent
"Everything is good! "
Karen 1-night trip
Posted 4 days ago
Fairfield Inn & Suites Jasper

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 $159 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.

Explore a world of travel with Expedia

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?

Another Oasis just 6 miles from Holiday World: Visitors like this Gentryville vacation home rental. It has air-conditioning and laundry facilities 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.

What can I see and do in Gentryville?

While exploring the area, visit family-friendly sights like Frosty's Fun Center, 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.