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Holiday houses in Webster County

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Top-rated holiday rentals in Webster County

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

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Top Guest favourite
The cabin's front porch features a covered area with two white swings and is framed by large, green shutters. Natural light enhances the welcoming facade, which is complemented by a metal roof and a simple entry door. Surrounding trees create a serene outdoor environment.
Cabin in Providence
4.98 out of 5 average rating, 81 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!

Guest favourite
Home in Madisonville
5 out of 5 average rating, 8 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, blender, pots, pans, cookie sheet, mixing bowls, etc. One queen bed, one king, triple bunk and single day bed. Full size inflatable mattress upon request. Bedrooms are upstairs. No smoking. No pets.

Top Guest favourite
A cozy living area is presented with a comfortable seating arrangement, featuring a light grey armchair and a patterned upholstered sofa. A flat-screen TV is positioned on a stylish console, and large windows allow natural light to illuminate the space, offering views of the outdoor setting.
Home in Madisonville
4.99 out of 5 average rating, 91 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!

A spacious porch features wooden rocking chairs and a swing, overlooking a tranquil private lake. The view includes lush greenery and a dock extending into the water, inviting moments of relaxation or enjoyment of scenic outdoor activities.
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 favourite
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
4.88 out of 5 average rating, 26 reviews

About 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 favourite
Cabin in Dixon
4.96 out of 5 average rating, 326 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.

Superhost
A single-story brick house sits on a large, grassy lot surrounded by open fields. The structure features a covered front porch with multiple seating areas. A spacious white garage is visible to the right, against a backdrop of blue skies and scattered clouds.
Home in Sebree
5 out of 5 average rating, 9 reviews

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.

Top Guest favourite
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, 86 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!

Guest favourite
The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.
Cabin in Dixon
4.91 out of 5 average rating, 532 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.

Superhost
Home in Madisonville
New place to stay

Nana's Place

Charming 3-bedroom, 2-bath home in a quiet Madisonville neighborhood. This cozy retreat offers a bright living space, fully equipped kitchen, and comfortable bedrooms for a relaxing stay. Enjoy the spacious backyard—perfect for unwinding or letting kids play. Conveniently located near local shops, dining, and attractions, it’s ideal for families, groups, or business travelers looking for comfort and convenience.

Home in Hanson

Farm#solitude

Minimum 30 days rental. The mobile home is safely on our farm, next to our farm house. Relax and enjoy a peaceful place to stay after a hard day at work.. listen to the birds as you sit on the deck enjoying the sounds of the country.. walk down to one of the three ponds, or stretch out on the couch and watch a movie, or read a book. The second bedroom is a twin trundle, so you can pull it out if needed.

Popular amenities for Webster County holiday rentals