Holiday rentals in Calhoun

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Top-rated holiday rentals in Calhoun

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Top guest favourite

A rustic log cabin is set against a backdrop of greenery, with a large Osage Orange tree providing shade. The cabin features a combination of natural wood exteriors and a modern addition, showcasing a warm and inviting entrance surrounded by well-maintained landscaping.

Cabin in Utica

Rustic Log Cabin Old Farm

Step back in time at this 1800s log cabin on historic DeLacey Farm. Surrounded by barns, wildlife, and wide-open fields, this rustic getaway sits on a nearly 100-year-old working farm—just minutes from Owensboro’s BBQ, bourbon, and small-town charm. Relax on the back deck with views of the original farm buildings, or head into town to explore the Green River Distillery and local eats. It’s the perfect blend of peaceful retreat and convenient access to everything Owensboro has to offer.

5.0 out of 5 average rating, 47 reviews

Top guest favourite

The living area features a spacious gray sofa with blue accent pillows, complemented by a circular wooden dining table. Two lamps provide soft lighting, and wall art adds visual interest. Large windows are dressed with light curtains, allowing natural light to fill the room.

Home in Owensboro

Comfortable 2 bedroom with 2 private baths, patio.

Conveniently located and newly renovated, near the Owensboro Greenbelt with nearby shopping, restaurants, and entertainment. Less than 10 minutes from downtown attractions including the Owensboro Convention Center, International Bluegrass Museum and Riverpark Center. Off street parking (2). Each bedroom has a private bath. Residential street in well established neighborhood. Less than five minutes from Owensboro/Daviess County Regional airport. Fully equipped kitchen, washer/dryer.

4.93 out of 5 average rating, 87 reviews

Top guest favourite

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.

4.96 out of 5 average rating, 350 reviews

Top guest favourite

The charming farmhouse showcases a red metal roof and a welcoming front porch supported by elegant white columns. Seasonal plants and decorative accents are placed along the entrance, complemented by a well-maintained lawn under the shade of surrounding trees.

Home in Calhoun

Smith House Back to the country

Take it easy at this unique and tranquil getaway. Come back to the country and travel back in time. The house was built in 1906 and has been painstakingly restored. Come get away from it all! Chickens provide eggs for breakfast. Friendly farm animals surround a pond stocked with fish. Bring your pole or use ones we will provide. Almost all of the furniture in the house is original to the house. New beauty rest mattresses on all beds. You can soak in the tub with views of the farm.

4.95 out of 5 average rating, 20 reviews

Guest favourite

The exterior of the home features a welcoming front porch with steps leading up to the entrance, framed by white railing. The facade is adorned with large windows and traditional shutters, complemented by a red roof that adds a pop of color.

Home in Calhoun

Calhoun Riverview House

Escape to this cozy riverside getaway in Calhoun, Kentucky! Nestled along the beautiful Green River, our two-bedroom, one-bath home offers a peaceful retreat surrounded by nature. Enjoy your morning coffee on the deck while taking in river views. With a fully equipped kitchen and comfortable living area this home is perfect for couples, friends, or small families looking for a serene stay. Book your stay at our Riverside Retreat and experience all that Calhoun has to offer!

5.0 out of 5 average rating, 18 reviews

Top guest favourite

A spacious living area features a large flat-screen television mounted on a dark wall. Two light gray sofas are arranged around a round coffee table on a textured rug. Soft lighting from two side tables complements the warm wooden flooring.

Home in Owensboro

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.

5.0 out of 5 average rating, 202 reviews

Superhost

A charming two-story historic home is displayed with a covered porch that features seating arrangements and a decorative lamp. Lush greenery surrounds the property, and a pathway leads to the front entrance, providing an inviting approach.

Home in Sacramento

Sacramento Sunshine

Bring the whole family to this great place with lots of room for fun. This Historic home has everything any Family or Large group could possibly need. Large kitchen , Coffee Station with Keurig and coffee pot, Dining room, plenty of parking for up to 8 cars. Right in the middle of downtown Sacramento Ky. Beautiful furnishings. Roku TV's. Sacramento is a Civil War town and is where General Nathan Bedford Forrest led his troops in Battle for the fist time.

4.65 out of 5 average rating, 23 reviews

Top 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

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.

4.91 out of 5 average rating, 558 reviews

Top guest favourite

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

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! Calhoun boat ramp is only 2 miles away. This property is centrally located, 25 miles north-east of Madisonville, 20 miles south of Owensboro.

4.94 out of 5 average rating, 48 reviews

Guest favourite

Home in Livermore

Two Rivers Retreat

Welcome to Two Rivers Retreat – Your Serene Escape in Livermore, KY! Nestled in the heart of Livermore, where the Green and Rough Rivers meet, our cozy two-bedroom home offers the perfect blend of comfort, style, and natural charm. Whether you're here to explore the local rivers, visit with family/friends, attend a community event, short-term work in the area, or simply enjoy a peaceful getaway, Two Rivers Retreat is your ideal home away from home.

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Cottage in Owensboro

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.

4.97 out of 5 average rating, 438 reviews

Top guest favourite

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.

4.96 out of 5 average rating, 238 reviews