Vacation rentals in Webster County

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Top-rated vacation rentals in Webster County

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Guest favorite

A cozy cabin stands surrounded by a well-maintained lawn, with three large windows adorning its bright red exterior. Lush greenery frames the structure, while a screened-in porch is visible, providing a serene view of the landscape. Tall trees offer shade nearby.

Cabin in Calhoun

4.86 out of 5 average rating, 21 reviews

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.

Top guest favorite

A serene lakeside view captures a quaint cabin reflected in calm waters. Lush green grass surrounds the water's edge, while trees frame the background under a blue sky dotted with clouds.

Cabin in Dixon

4.96 out of 5 average rating, 295 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.

Guest favorite

The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.

Home in Owensboro

4.96 out of 5 average rating, 145 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.

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, 60 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 favorite

The cottage features a welcoming front porch adorned with red shutters and a bright red door. Two large, round rocking chairs are positioned on the porch, surrounded by greenery and a blue planter. The pathway leads to the spacious entrance.

Cottage in Maceo

4.96 out of 5 average rating, 171 reviews

Hattie's Hill Cottage

Cottage sits behind our home (see photo). NOTE- Main house may have large groups. Pool and outside areas share spaces. Near Owensboro, Rockport, Hawesville & Lewisport. There is ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi. We have a Smart TV you may use your Netflix and so on with. Kitchen is well stocked with necessities. Eating/work space is provided. Comfortable recliner chairs. Access to the grounds.

Superhost

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

4.9 out of 5 average rating, 506 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.

Guest favorite

The cabin is showcased with a modern architectural design, featuring a wooden facade and large windows that allow for natural light. The structure sits on a grassy area, with a clear blue sky enhancing the overall appearance.

Cabin in Robards

4.94 out of 5 average rating, 119 reviews

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.

Top guest favorite

A charming cottage is nestled among tall trees, surrounded by lush greenery. A stone pathway leads from the foreground to the front steps, which are framed by well-maintained landscaping and vibrant foliage. Sunlight filters through the leaves, creating a serene outdoor setting.

Cottage in Owensboro

4.97 out of 5 average rating, 389 reviews

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.

Guest favorite

A cozy living area features a comfortable sofa with decorative pillows and a welcoming atmosphere. A coffee table is centered beneath a tasteful arrangement of candles and plants. Warm lighting is provided by two side tables with lamps. A front door with an oval window adds charm.

Home in Corydon

4.95 out of 5 average rating, 198 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.

Top guest favorite

The front exterior of the cottage features a welcoming entrance highlighted by a decorative wreath on the door. Two symmetrical windows are positioned on each side of the entrance, surrounded by well-maintained landscaping, including colorful flower beds and neat shrubs. A stone pathway leads to the door.

Home in Owensboro

4.95 out of 5 average rating, 229 reviews

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.

Top guest favorite

A single-story cabin with wooden siding and a green metal roof is featured. A spacious front porch with railing provides outdoor seating options. Surrounding the cabin are patches of grass and gravel, with trees visible in the background, creating a natural setting.

Vacation home in Equality

4.95 out of 5 average rating, 108 reviews

JACS COUNTRY CABINS SHAWNEE 2

COZY 1 BEDROOM, 1 BATH CABIN AT THE EDGE OF THE SHAWNEE NATIONAL FOREST. LOCATED 10 MILES FROM GARDEN OF THE GODS AND & 1 MILE FROM GLENN O JONES LAKE. IT SITS BEHIND JACS PLACE (A BAR/CONVENIENCE STORE) AND 2 MILES FROM A LAUNDRY MAT IN EQUALITY. WE PROVIDE COFFEE BUT THE CLOSEST GROCERY STORE IS ROUGHLY 10 MINS AWAY IN ELDORADO, SO PLAN, PACK SNACKS/FOOD ACCORDINGLY.

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, 23 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.