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Vacation rentals in Webster County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Webster County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Madisonville
5 out of 5 average rating, 10 reviews

Peaceful Retreat

Close to downtown Madisonville, Kentucky Sports Factory/Sports Plex and one mile from Mahr park (walking trails, picnic pavilions, kayak launch,etc). Private backyard with patio, table/chairs and BBQ grill. Home has Smart TV w/ streaming channels, DVD player, WiFi, Keurig and drip coffee, toaster, pots, pans, cookie sheet, mixing bowls, etc. One queen bed, one king, single over full bunk and single day bed. Full size inflatable mattress upon request. Bedrooms are upstairs. No smoking. No pets.

Top guest favorite
Cabin in Providence
4.98 out of 5 average rating, 87 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
Home in Madisonville
4.99 out of 5 average rating, 98 reviews

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.

Home in Clay

Brown’s Bar

Newly updated, simply decorated, spacious house featuring 4 bedrooms (sleeping for 10), 3 baths, living room, fully stocked kitchen, dining room(seating for 10), laundry room! It is surround by corn fields & has a stocked pond! Mofitts lake is 25 minutes away. Hunting includes Blackford Oaks WMA (0.5 miles), Big Rivers WMA (18 miles), and Higginson-Henry WMA (19 miles). The cabin is located 6 miles outside of Clay, Ky and less than 30 miles from Providence, Dixon, Sturgis, and Marion, Ky!

Cabin in Clay

Private Lake & Dock: Log Cabin, 2 Mi to Clay!

Newly Renovated | Furnished Outdoor Space | Scenic Views Lean into waterfront living at this Clay vacation rental, 'Hilltop Hideaway!' Situated between Marion and Madisonville, this 1-bed 1-bath cabin boasts a 2-acre private lake and a dock with a swim ladder, making it easy to enjoy aquatic activities. Spend time fishing, splashing around, or sipping your favorite drink while swinging on the porch. Ready to venture out? Go boating on the Ohio River or explore Cave-In-Rock State Park!

Top guest favorite
A cozy cabin exterior is illuminated by string lights, highlighting the inviting porch. A red door provides a pop of color, while a folding chair and picnic table create a welcoming space for relaxation. The surrounding area is dark, enhancing the cabin's warm glow.
Tiny home in Sebree
4.89 out of 5 average rating, 28 reviews

Over Yonder

Come to the country and enjoy life's simple pleasures! Sit on the porch and watch the turkeys strut and the deer graze. Hear the owls screech at night and the coyotes yip! Head on down to the creek and warm up with a fire in the fire pit. There's a barbecue grill to cook up the perfect steak! Inside you will find cozy charm and some modern amenities! There's central heat and air to keep you comfortable, a microwave oven, coffee maker, a full size shower, and memory foam mattresses.

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
4.96 out of 5 average rating, 336 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 modern duplex with a crisp white exterior is presented, featuring a dark roof and large windows. Two front doors, one for each unit, are framed by charming landscaping. Surrounding trees display vibrant autumn foliage, enhancing the inviting outdoor space.
Apartment in Madisonville
5 out of 5 average rating, 98 reviews

Modern, Quiet, Hidden Gem: Manna House (5)

Kick back and relax in this peaceful, brand new, stylish space. Located close to town yet feels like a hidden country paradise. This unit is one of two units available at a duplex situated on 5 acres. With 10 foot ceilings this one bedroom feels so much bigger! It offers a walk in tile shower, King bed and Queen sleeper sofa, full kitchen with Quartz countertops, KitchenAid appliances, and includes full size stacked washer/dryer. We think you will love it here!

Top guest favorite
Cabin in Dixon
4.91 out of 5 average rating, 546 reviews

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.

Top guest favorite
A modern single-story home is framed by a spacious porch with several seating arrangements. Large windows illuminate the interior, while a scenic view of open farmland extends into the background. Mature trees provide shade to the front yard, enhancing the country setting.
Home in Clay
4.98 out of 5 average rating, 48 reviews

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.

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, 41 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.

Home in Madisonville
New place to stay

Your perfect Madisonville retreat

Welcome to your perfect Madisonville retreat, located only minutes from downtown and Hanson. Enjoy coffee or tea while sitting on your private deck surrounded by nature or relax in the TV room or work without interruptions. The house is on a very quiet road and surrounded by woods.

Popular amenities for Webster County vacation rentals