Vacation rentals in Webster County

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Top-rated vacation rentals in Webster County

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Top guest favorite

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

4.97 out of 5 average rating, 60 reviews

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!

Top guest favorite

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

4.97 out of 5 average rating, 289 reviews

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.

Top guest favorite

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

4.97 out of 5 average rating, 88 reviews

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.

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, 500 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.

Guest favorite

A wide path meanders through a grassy area surrounded by lush trees. Sunlight filters through the foliage, creating dappled patterns on the ground. In the distance, a calm body of water reflects the blue sky and green landscape.

Home in Madisonville

4.93 out of 5 average rating, 28 reviews

Great space, no cleaning fees, City park view.

Forget your worries in this spacious and serene space. A home away from home. 3 bedrooms, each with Tv. Spacious kitchen and living room. Washer and dryer in basement. Beautiful view of lake and wildlife. Basement gives added space to stretch out. Ping pong, Ms. Pac-man, foosball, corn hole and kids toys. Advance notice for use of hammock, bicycles or kayak. Need more space, second home available next door for booking.

Guest favorite

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

4.95 out of 5 average rating, 195 reviews

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.

Guest favorite

A marble-topped coffee table displays a stack of vintage records alongside a book titled 'Doodle Revolution.' The records, with colorful labels, are arranged in a casual yet appealing manner on the soft, patterned rug.

Home in Owensboro

4.85 out of 5 average rating, 150 reviews

The Bluegrass Barbie

Welcome to Owensboro, KY home to the ONLY Bluegrass Museum Hall of Fame on PLANET EARTH! Minutes away from Owensboro Convention Center, ALL sports facilities, world class dining, & one of the MOST UNIQUE stays in Owensboro, KY! Great home to stay at for sports tournaments, visiting family, visiting Holiday World, or just a weekend away! And don't forget to check out The Green River Distillery!

Guest favorite

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

4.97 out of 5 average rating, 111 reviews

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!!

Guest favorite

Bungalow in Owensboro

4.98 out of 5 average rating, 138 reviews

Bluegrass Bungalow: Historic Charm, Modern Comfort

Welcome to the Bluegrass Bungalow, a charming 1924 two-bedroom, one-bath home that seamlessly blends historic charm with modern amenities. Located near the Ohio River and downtown, this cozy retreat is just moments from top restaurants and shopping. Enjoy the preserved vintage details alongside a fully renovated kitchen and bath, including a spacious walk-in shower.

Top guest favorite

A charming house stands amidst tall trees, softly illuminated by outdoor lighting in the evening. The two-story structure features a spacious deck and large glass doors, blending seamlessly with the surrounding woodland. A gravel path leads up to the entrance, enhancing the tranquil setting.

Home in Webster County

5 out of 5 average rating, 18 reviews

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.

Top guest favorite

A kitchen countertop is showcased with a coffee maker and a wooden rack displaying various coffee pods. A small box containing assorted tea bags is positioned nearby. A decorative sign reads 'Happiness Homemade with Love & Butter,' adding a welcoming touch.

Home in Madisonville

5 out of 5 average rating, 73 reviews

Four-Fifty on Stagecoach

Have fun with the whole family at this newly furnished and stylish place. This cozy home is Located in a quiet & safe rural area north of Madisonville. If you need additional space or have interest in a second property check out our Whippoorwill Farmhouse located just up the road.