Vacation rentals in Gentryville

Chestnut Street Retreat

A quaint and friendly neighborhood, with large backyard for kids playing, relaxing in the breeze way with morning coffee, or fun by the fire pit. Biking or walking around the neighborhood is safe and fun on a sunny day. Though you may feel in the country you are very close to downtown Huntingburg, 8 miles to Downtown Jasper. House is cozy and relaxing for a weekend away or if you're looking for activities Holiday World (18 Miles), Patoka Lake, French Lick Casino & West Baden Hotel (27 Miles).

Happy Hollow cottage @ Patoka

Nestled amidst a wooded lot this newly remodeled cottage offers a peaceful escape at Patoka Lake. This cozy cottage has everything you need to create unforgettable memories. Complete with hot tub & firepit this well-equipped cottage gives you all the comforts for a hassle-free stay. Perfectly located minutes away from Patoka Lake main entrance, easy to access the lake's pristine waters for boating, swimming, or fishing plus hiking trails. Also, close proximity of local wineries & restaurants.

The Storehouse - unique retreat near Holiday World

The Storehouse, a church built in the 1890s, is nestled in the serene backdrop of Grandview, Indiana. This former sanctuary has been thoughtfully transformed into a 3 BR home, perfectly blending old-world charm with contemporary amenities. You will love the original hardwood floors and stained glass windows in every room. Less than 15 min. from Holiday World and Lincoln State Park, there is much to do. Return and unwind in the private hot tub or gather around the fire pit under the stars.

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Shaded Log Cabin/Swim Spa 2 miles to lake entrance

Newly remodeled Log Cabin with new pillows, sheets, towels. Wooded property next to creek. Enjoy screened in front porch or the back deck with 14-foot Swimspa, fire pit & grill in quiet wooded setting. Free State Park pass saves $7 day. Downstairs Master with king bed. 2 queen beds in loft bedroom. Electric fireplace w/5 settings, AC/heat, High speed wifi/internet, SMART TV with Bluetooth sound bar, Direct TV, Washer/dryer. Ice maker. WE ALWAYS OFFER EARLY CHECKIN & CHECKOUTS WHEN AVAILABLE.

The Woodford Retreat Cottage

Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines Cabin. We are 12 miles from Holiday World. The Cabin has its own private hot tub and also includes a private fire pit and we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. Our other rentals are Eagles Nest (3BR option) and Eagles Nest Plus (4BR option). Starting with the 2026 season check out will be at 10 am ON SUNDAYS ONLY, 11AM all other days.

Nature Lovers Retreat

This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

The Cabin - Near Holiday World & Splashin' Safari

If you'd like a true log cabin feel while staying on a beautiful, serene wooded 10 acre plot of land, this is the place for you and your friends/family! This small cabin has been reconstructed after being transferred to this location by the owner and his son. All of the decor and fixings are antique in style to fit the log cabin feel, to bring you back to the good ole days.