Holiday rentals in Webster County

Little Red on the Green River

Little Red on the Green is the perfect getaway if you enjoy the peacefulness of watching the river flow downstream. This simple, cute, cozy, 600 square foot, one room cabin is sure to be enjoyed. The private riverfront, property is just steps from the river bank. If you like to fish, this might be the perfect spot! If you have a boat, the Calhoun boat ramp is only 2 miles away. This property is centrally located - 25 miles north-east of Madisonville, 20 miles south of Owensboro, Ky.

Crouse’s North Ninety Lake House

If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

Basement Apartment 2 Bedroom Kitchen Washer Dryer

We are renting the entire basement level of our house. It is a completely private area for you to stay , with a key lock entry. Open floor plan in this basement is perfect for a family traveling or groups traveling for work. It is approximately 1700 sq feet. Fully stocked kitchen with new pots and pans, coffee maker, dishes, glasses, refrigerator, new microwave, stove, washer and dryer. Two Bedrooms one King the other a Queen Bed with closets and dressers.

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

REINE CABIN at Farmer and Frenchman

EAT. TASTE. STAY. Year round view, seasonal flavor. The property features a winery/cafe, a vineyard, walking trails, and a 360 view of countryside. Created in the spirit of rustic elegance, the Cabin's lavish accents are sure to impress. Enjoy dinner in the cafe, walk the trails, snuggle in for the night, order breakfast in bed and a morning yoga session on the patio. Enjoy the ambiance of Kentucky's agrarian heritage with modern and stylish amenities.

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.

Shelton Farmhouse

Take it easy at this unique and tranquil getaway. Watch beautiful sunsets and get close to nature while sitting on a west facing patio or the large sitting porch complete with rocking chairs. You can definitely get away from it all here. Home sits in the middle of 120 acres of farmland now held in the Conservation Reserve Program which promotes wildlife habitat in beautiful Western Kentucky.

2 bedroom w/free on-site parking. Near downtown

When you stay at this centrally located accommodation, your family will be close to everything. The backyard is fenced in and has a fire pit. The sofa has one pullout bed. The master suite has one queen bed. The second bedroom has two XL twin beds. Complete kitchen with dishwasher, plates, utensils, and washer and dryer. No more than two pets. Pets must be under 30 pounds each.

Downtown 1 bed & 1 bath studio guest house

Enjoy easy walkable access to downtown Henderson festivals, restaurants, and river fun when you stay in our guest house. This one-bedroom 1 bathroom studio space has a private entrance, free parking, and access to an outdoor deck with seating Enjoy ammenities such as a queen-size mattress, 50" smart tv, full-size refrigerator, blow dryer, Keurig, and more.