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

Home in Madisonville

4.99 out of 5 average rating, 76 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.

Guest favourite

Cabin in Dixon

4.96 out of 5 average rating, 305 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 favourite

Apartment in Madisonville

5 out of 5 average rating, 18 reviews

Modern, Quiet, Hidden Gem: Manna House (7)

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, queen size adjustable bed, queen size 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

Home in Owensboro

4.94 out of 5 average rating, 165 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 favourite

Home in Owensboro

4.99 out of 5 average rating, 165 reviews

Midtown Cottage- Self Check-In & Centrally Located

Enjoy your stay in Owensboro, KY in this cozy, warmly decorated home! This home is centrally located to everything Owensboro has to offer, a short drive from downtown and the award winning riverfront. Wifi and parking are included. Enjoy a stylish experience at this centrally-located home. You will enjoy relaxing either in the home or the lovely backyard space. Whether you are in town for work or play indulge in the comfort and tranquility of this modern house.

Guest favourite

Cabin in Dixon

4.9 out of 5 average rating, 512 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 favourite

Cabin in Robards

4.94 out of 5 average rating, 120 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 favourite

Cottage in Owensboro

4.97 out of 5 average rating, 400 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.

Top Guest favourite

Home in Corydon

4.96 out of 5 average rating, 206 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 favourite

Home in Madisonville

4.94 out of 5 average rating, 31 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, foosball, corn hole and kids toys. Advance notice for use of hammock, bicycles. Need more space, second home available next door for booking.

Superhost

Home in Owensboro

4.85 out of 5 average rating, 159 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 favourite

Home in Clay

4.97 out of 5 average rating, 38 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.