Vacation rentals in Webster County

4.97 out of 5 average rating, 58 reviews

The front porch of the cabin is presented, featuring rocking chairs and a swing, set against a backdrop of well-maintained greenery. The porch is complemented by a metal roof and a beige and green exterior, inviting relaxation in a rural setting.

Cabin in Providence

Valley View Lodge in Western Kentucky

Come enjoy a cabin stay without roughing it! We are located in the heart of whitetail deer country in Western Kentucky. Featuring a small lake and a front porch complete with swing, the cabin sits next to woodlands. A gas log fireplace stands ready for those extra cold evenings and the large attached garage is perfect for hunting gear and storage. The property is private yet close to the highway and less than 4 miles from food, fuel, and other essentials. There is ample parking and a fire pit!

4.98 out of 5 average rating, 59 reviews

A cozy fire pit area is set in an open green space, featuring two red Adirondack chairs arranged around a central fire pit. The surrounding landscape includes expansive fields and distant trees, creating a serene outdoor atmosphere.

Home in Madisonville

Whippoorwill Farmhouse

Relax with the whole family at this peaceful place to stay. Located just two miles from the city, this fourth generation 1933 farmhouse has been recently remodeled inside and out. Enjoy relaxing in the enclosed front porch or the wrap around deck with views of the 180-acre working crop farm. Guests can enjoy a nice stroll around the farm, drop a line in the stocked pond, and spend time around the fire talking and roasting smore's. Ask your host about group events and hayrides around the farm.

An open-concept living area is highlighted by modern furnishings and natural light. A sectional sofa is paired with a circular coffee table, while a well-equipped kitchen with bar seating is visible in the background. Stylish artwork complements the neutral color palette.

4.94 out of 5 average rating, 111 reviews

Bluegrass Commons

You will be close to everything when you stay at this centrally-located three bedroom two bath home right off the bypass that is a short drive to anywhere in Owensboro, KY for any business travelers. This is a brand new construction home in Bluegrass Commons neighborhood! New furnishings and the home sleeps 6 comfortably. Split bedroom with an open concept perfect for families. Fully stocked kitchen with a keurig coffee station. Large backyard perfect for entertaining or just grilling.

4.97 out of 5 average rating, 286 reviews

A charming cabin is reflected on the calm surface of a pond, surrounded by lush greenery and trees. Fluffy clouds are visible in the blue sky above, complementing the peaceful rural setting. A small boat is moored nearby, adding to the serene atmosphere.

Cabin in Dixon

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.

A wide view of a calm river scene is presented, with a grassy slope leading down to the water. A boat is docked near the shore, while individuals can be seen walking along the pathway. The sky is clear with a few scattered clouds.

4.95 out of 5 average rating, 133 reviews

The Cozy Cottage

Join us for a relaxing stay at the Cozy Cottage! Inside you will find everything you need to make for a cozy stay whether you’re with us for short weekend or a month. Outside you will find plenty of spaces to sit and enjoy the view of the Ohio River just 2 blocks away. The Cozy Cottage is conveniently located less than 5 minutes from downtown Owensboro and popular attractions such as the Convention Center, Bluegrass Museum, Botanical Gardens, and Jack C. Fisher Park.

4.96 out of 5 average rating, 84 reviews

A well-organized beverage station is displayed, featuring assorted tea bags, coffee pods, and creamers. A variety of flavored teas and coffee options are arranged neatly, along with cups and a selection of sugar packets, ensuring a convenient experience for guests.

Cabin in Corydon

The Geneva Cabin

The Geneva Cabin is one of a kind (not in the woods) and has everything you need to enjoy whatever occasion brings you to the area. Located less than 2 miles from the wildlife refuge, 10 min to downtown Henderson, 7 mi to I-69 the property sits in the middle of a quiet dead-end street. Right in the middle of anywhere anyway your journey takes you. 55” TV, sofa bed and recliner in living room, WIFI, washer & dryer. Fully equipped kitchen. Large parking area.

4.97 out of 5 average rating, 380 reviews

Lush trees with vibrant green and yellow leaves create a canopy in a tranquil forest. Sunlight filters through the branches, illuminating the forest floor covered in fallen leaves. The scene conveys a serene natural environment, ideal for exploration and relaxation.

Cottage in Owensboro

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.

4.8 out of 5 average rating, 15 reviews

A large, grassy area is framed by mature trees, providing shade and a sense of tranquility. The river is visible in the background, where a boat can be seen floating along the water, enhancing the natural setting.

Cabin in Calhoun

Little Red on the Green River

Are you a fisherman? Maybe you prefer the peacefulness of watching the river flow past, then Little Red on the Green will be the perfect getaway. 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. The Calhoun boat ramp is only 2 miles away. This property is located 25 miles north-east of Madisonville, and 20 miles south of Owensboro, Ky.

Superhost

An outdoor porch is illuminated by warm string lights, creating a cozy setting. Comfortable seating is arranged around a table, surrounded by wooden railings. The natural backdrop features tall trees, enhancing the serene atmosphere of the space.

Cabin in Dixon

4.9 out of 5 average rating, 496 reviews

Handcrafted Cabin in Woodsy Heaven

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.

4.96 out of 5 average rating, 191 reviews

A covered patio features a charcoal grill and six black chairs surrounding a table. A serene lake is visible in the background, with lush greenery framing the scene. A wheelbarrow and decorative plants enhance the inviting outdoor atmosphere.

Home in Corydon

The Farm

Step away from the fast pace of daily life and enjoy family, friends and the peace of country living. Secluded modern farm house, that began as a log cabin, situated on approximately 100 acres of crop fields and includes a scenic lake. This property has been in our family for over 100 years. It has been lovingly furnished and decorated for a one of a kind stay. We want our guests to unplug, refresh, and renew.

4.97 out of 5 average rating, 109 reviews

A serene view of a river stretches out under a colorful sky, reflecting the greenery along the banks. A bridge spans the water in the distance, framed by trees showing hints of seasonal color. The riverbank is lined with grass and natural rock formations.

Home in Livermore

River Trails Inn

Historic two story home with three bedrooms and 3 1/2 baths, circa 1900, located in the old downtown district of the quaint river town of Livermore, Kentucky, just two blocks from the confluence of the Green and Rough Rivers and our expansive riverfront recreation complex. River kayaking and canoeing and biking trails on marked low-use county roads are right in your back yard!!

5 out of 5 average rating, 16 reviews

Home in Webster County

Newly Listed! Secluded 3 BR house in the Woods!

Escape to a tranquil oasis nestled on a wooded hillside with our charming house available for short term. Located just a short drive from Henderson, Madisonville, Owensboro, or Evansville this serene property offers the perfect blend of natural beauty and modern comfort. Each bedroom includes a television and house is Starlink equipped for Internet access.

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Other great vacation rentals in Webster County

4.94 out of 5 average rating, 50 reviews

A cozy place that helps you feel right at home.

HeatherRating, 5 stars1 month ago

The property was exceptionally clean and well-maintained, and Patty was incredibly responsive to all of our questions. We felt very comfortable and well-cared for during our stay.

Vacation home in Owensboro

A vibrant dining table is set with a large green plate containing rice, beans, and a filled tortilla, topped with a drizzle of sauce. Glasses of beverages, chips in a basket, and various sauces accompany the meal, creating an inviting atmosphere.

4.93 out of 5 average rating, 127 reviews

The little big cozy house

KatherineRating, 5 stars3 weeks ago

We enjoyed our stay at Francisco’s place! It was so clean and homey. Both us and our pets felt at home. It’s close to anything you need but still private and enough to provife quiet comfort. We could not be happier with our stay! And we will definitely stay again!

5 out of 5 average rating, 15 reviews

Green River Getaway

ToriRating, 5 stars3 weeks ago

10/10 recommend this place! The host is amazing outreached before and during stay to check in on us ans ensure we were settled in. Property was gorgeous. Plenty of space foe time with family. Perfect resting and close to by pass. One of my best airbnb stays.

A serene river view is captured during sunset, showcasing a gradient of warm colors in the sky. A swing can be seen hanging from a tree, providing a peaceful spot to enjoy the natural surroundings.

4.93 out of 5 average rating, 211 reviews

Riverview Escape

RonaldRating, 5 stars3 days ago

A nice place to relax after a hard days work

The cottage's exterior is illuminated at night, revealing a classic architecture with a welcoming front porch and two white rocking chairs. A bold pink door serves as a focal point, surrounded by soft landscaping and a well-defined walkway leading to the entrance.

4.94 out of 5 average rating, 144 reviews

Cottage by the River & Convention Center

JaimeRating, 5 stars3 weeks ago

Quiet, peaceful. Skip and a walk to downtown OWB. Great location for BBQ fest. Fast response from Host to questions. Didn’t use backyard or patio as we were out and about all day and night. 3 bdrms but only stayed in one. Would rent again.

A modern kitchen features light blue cabinets and stainless steel appliances, including a refrigerator and a gas stove. A black countertop complements the color scheme, while a small area rug is placed near the sink. Natural light is visible through a window overlooking an outdoor space.

4.96 out of 5 average rating, 28 reviews

Cozy Retreat, modern Amenities

AdamRating, 5 stars3 weeks ago

It was a peaceful stay. Clean and tidy. Close to restaurants and stores. A nice patio to sit and relax in the shade. I would rent it out again when I come back to Owensboro.