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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Guest favourite

Cabin in Dixon

4.97 out of 5 average rating, 234 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.

29 Mar – 5 Apr

$1,798 AUD total

Guest favourite

Cottage in Maceo

4.97 out of 5 average rating, 144 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 ONLY ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi ..Smart TV... use your Netflix and so on with this TV ...... Kitchen has everything you need ..Eating/work space. Comfortable recliner chairs ... Use of pool/ plenty of places to roam on farm .

26 Aug – 2 Sept

$940 AUD total

Guest favourite

Cabin in Corydon

5.0 out of 5 average rating, 19 reviews

1 bedroom cabin

Our custom built 14ft x 40ft cabin has everything you need to enjoy whatever occasion brings you to the area. 10 min to downtown Henderson, 7 mi to I-69 or a shot from the Sloughs Wildlife Refuge, the property is located on a quiet dead-end street. Right in the middle of anywhere anyway your journey takes you. 55” TV, leather recliners, WIFI, washer & dryer. Fully equipped kitchen. Keurig, French Press or drip we have your coffee covered. Plenty of off street parking.

24 Sept – 1 Oct

$1,301 AUD total

Guest favourite

Home in Marion

5.0 out of 5 average rating, 25 reviews

Waterfront Farm Stay w/ Game Room

Escape the city noises and come enjoy what makes Western KY a hidden gem. Slow down and relax. Located 3 miles outside of Marion KY, this waterfront lodge is filled with wild-game and decorations that will give you the feel of a cozy hunting cabin. The fire pit is ready for marshmallows and memories to be made. Walk out on the dock and feed the fish. Game room in garage. NO WIFI. HORSEBACK RIDING LESSONS AVAILABLE for all levels of riders. We look forward to having you!

17 – 24 July

$1,512 AUD total

Guest favourite

Home in Elizabethtown

5.0 out of 5 average rating, 31 reviews

Creekside Serenity Stop

Engulf yourself on a secluded eight acres of property surrounded by the magnificent Shawnee National forest. Enjoy a refreshing dip in our private spring fed creek, watch wildlife, hike our local trails, kayak Whoopie cat lake, stargaze and let your worries drift away. We are centrally located to many sites and just a short 15 minute drive to Garden of the Gods and Rim rock/pounds hollow lake. Cave-In-Rock is only about 20 minutes, among others within 30 minutes.

8 – 15 Sept

$1,625 AUD total

Guest favourite

Apartment in Madisonville

5.0 out of 5 average rating, 50 reviews

Manna House (5): A perfect place to feed the soul!

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!

2 – 9 July

$1,988 AUD total

Guest favourite

Home in Madisonville

4.84 out of 5 average rating, 43 reviews

3 Bedroom Home on a quiet street.

Located close to everything in Madisonville. Only about a 5 minute drive to most parks, hospitals and all the local spots downtown. Smoking and vaping on the property is not allowed. Minutes from Elmer Kelly Stadium and surrounding parks 25-30 minutes to Dawson Springs and the beautiful scenery at Pennyrile State Park. Ideal for traveling nurses, co ops at local factories or those traveling for family events, wedding weekends, and visiting friends.

8 – 15 Apr

$1,635 AUD total

Superhost

Cabin in Slaughters

4.86 out of 5 average rating, 63 reviews

Cozy Green River Cabin Getaway with great view

Take it easy at this unique and tranquil getaway. 2 Bedroom, 1 bath, living area, full kitchen, and deck overlooking the Green River awaits you. Perfect getaway for the week or weekend. You will be the only guest at the cabin and have full use of the upstairs area as basement area may be future use. This cabin is less than 2 miles from a public boat dock where you can launch and enjoy the day on the River. Convenient to Calhoun and Madisonville.

6 – 13 Oct

$1,144 AUD total

Guest favourite

Cottage in Owensboro

4.97 out of 5 average rating, 326 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.

4 – 11 Jan

$999 AUD total

Guest favourite

Cabin in Dixon

4.92 out of 5 average rating, 431 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.

11 – 18 Oct

$1,079 AUD total

Guest favourite

Home in Corydon

4.97 out of 5 average rating, 152 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.

22 – 29 Oct

$2,351 AUD total

Guest favourite

Home in Madisonville

4.95 out of 5 average rating, 20 reviews

Downtown Charm — walk anywhere!

This centrally located, charming downtown home is the perfect place for your short term stay in Madisonville, KY. Set up with professionals in mind, you’ll have everything you need at your finger tips… right down to an espresso & a travel mug for your busy morning. Within blocks to medical facilities, the Justice Center, downtown shops, restaurants, bars, & more. No pets please.

9 – 16 Feb

$1,638 AUD total