Holiday houses in Webster County

4.97 out of 5 average rating, 59 reviews

Cabin in Providence

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!

5 out of 5 average rating, 36 reviews

Cabin in Maceo

Lakeside Cottage

Set in the treetops, our recently renovated cabin has everything you need for a unique relaxing stay! Bring your kayak, canoe etc... We are right on the lake with our own dock for come and go all day fun! Decorated in restful tones for maximum relaxation and boasting lots of amenities, it's only a short 15-20 minute drive into Owensboro, a quaint River town full of eateries, special events and lots of shopping! We love hosting birthdays, anniversarys and honeymoons! No cleaning fee!

4.94 out of 5 average rating, 114 reviews

Home in Owensboro

Bluegrass Commons

You will be close to everything when you stay at this centrally-located three bedroom two bath home right off the bypass that is a short drive to anywhere in Owensboro, KY for any business travelers. This is a brand new construction home in Bluegrass Commons neighborhood! New furnishings and the home sleeps 6 comfortably. Split bedroom with an open concept perfect for families. Fully stocked kitchen with a keurig coffee station. Large backyard perfect for entertaining or just grilling.

4.97 out of 5 average rating, 288 reviews

Cabin in Dixon

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.

4.97 out of 5 average rating, 86 reviews

Cabin in Corydon

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.

4.81 out of 5 average rating, 16 reviews

Cabin in Calhoun

Little Red on the Green River

Are you a fisherman? Maybe you prefer the peacefulness of watching the river flow past, then Little Red on the Green will be the perfect getaway. 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. The Calhoun boat ramp is only 2 miles away. This property is located 25 miles north-east of Madisonville, and 20 miles south of Owensboro, Ky.

Superhost

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.

4.93 out of 5 average rating, 27 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.

4.95 out of 5 average rating, 194 reviews

Home in Corydon

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.

5 out of 5 average rating, 18 reviews

Home in Webster County

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.

5 out of 5 average rating, 70 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.

4.99 out of 5 average rating, 134 reviews

Farm stay in Junction

Entire home Dapple Horse Hill's Dogwood Hill House

Freshly remodeled 3 bedroom 2 bath home in the Shawnee National Forrest with trail access. Situated on a dead end lane, quiet and peaceful. Relax, recharge close to Garden of the Gods, Glen O Jones Lake, Pounds Hollow and Rim Rock. Horses welcome!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Webster County holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Webster County

5 out of 5 average rating, 13 reviews

Cabin in Owensboro

Poolside Serenity Cabin

HeidiRating, 5 stars3 weeks ago

Loved our stay here. Place was easy to find. It was nice and clean. Lori and her husband were very nice and chatty. Very responsive too! It was a wonderful home away from home! Would recommend and do plan on staying here in future visits!

5 out of 5 average rating, 18 reviews

Home in Owensboro

Green River Getaway

JeffRating, 5 stars5 days ago

Beautiful updated home! Had high end appliances, tastefully decorated and very clean and comfortable. Beds were super comfortable! Loved the great water pressure.Enjoyed the big screen tvs. Outside was very manicured. Enjoyed the big covered porch as it rained a lot. Big dock and fire pits with wood our favorite Saw an eagle salamanders and a toad. Thanks so much for having us! God bless! Jeff and Mike

4.86 out of 5 average rating, 7 reviews

Queen’s House

SusanRating, 5 stars1 month ago

Even though we had to cancel our trip due to illness, Penelope was extremely accommodating. We'll try to rebook in June.

Superhost

Apartment in Henderson

4.76 out of 5 average rating, 29 reviews

Henderson Haven | KING 2BD/1BA Apartment

BettyRating, 5 stars6 days ago

The unit was exactly as pictured. Great deal for a 2 king size bedroom unit! Neighborhood was very quiet and we were there for the weekend for the blues festival. If available next year, we will be back.

4.9 out of 5 average rating, 30 reviews

Home in Bremen

The Tumbling K

ChristyRating, 5 stars4 weeks ago

This rental home was exactly what we were looking for. We stayed for several days and felt very comfortable there. The host has obviously been working to update everything inside. There are still a couple things that could use an upgrade, but everything was clean and comfortable. Host was always responsive. It’s in nice and quiet and comfortable country setting while being 10 to 15 minutes from Central City. We would definitely stay here again.

4.84 out of 5 average rating, 64 reviews

3 bedroom, close to downtown & KY sports factory

ChriscindaRating, 5 stars1 week ago

Andrew, was very accomodating. He left step by step instructions for everything. I never had to bother him except to request a late check out. However when I did reach out he responded immediately. Everything was superb! It was very nice to come home to visit and actually stay on one of the streets I grew up on. I would definitely recommend his location to friends and family. The house was clean very inviting and felt just like home. Thank you Andrew!

5 out of 5 average rating, 16 reviews

Barn in Marion

Quiet Secluded tiny home

BobbyRating, 5 stars3 months ago

The place was our stay was great! We had one hiccup with the door code, but with very fast response time from the host resolved the issue within minutes. Description was spot on and would stay again.