Vacation rentals in Calhoun

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Calhoun

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1

Superhost

A single-level home is featured with a welcoming front porch swing, framed by greenery. The entrance includes a ramp, allowing for easy access. The yard includes a pathway that leads to the front door, enhancing the welcoming atmosphere of the residence.

Home in Sacramento

4.75 out of 5 average rating, 16 reviews

CROSSROADS COTTAGE

This home welcomes you with a front porch swing and a small side deck to visit with family and friends; the side has a ramp entrance. WIFI and TV are included. Nice size kitchen and livingroom for relaxing and visiting. The office has a daybed with trundle - great for children and teens. Churches, restaurants, bank, and post office are in walking distance. Grocery, Dollar General, hair/nail salon & fashion, gas stations, auto mechanic shops, hardware, and funeral home are within one mile.

LocationValueCondition

Top guest favorite

An open concept living area features a plush gray sofa with accent pillows, complemented by a modern coffee table on a textured area rug. The kitchen area includes wooden cabinets and bar seating, while natural light brightens the space through a nearby window.

Home in Owensboro

5.0 out of 5 average rating, 196 reviews

4bed3BR 35 to HolidayWorld/Near Conv Ctr/Fisher Pk

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv! Home is 3 miles from Convention Ctr, Bluegrass Museum, Science Museum, Botanical Garden. It’s also 4 minutes from baseball fields (Fischer), Thompson Berry( soccer), 35min to Holiday world, private and fenced backyard with lighted patio. Home is well stocked with ALL you may need! If the home is empty previous night, early check in, no charge! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen, book now!

FamilyValueTV

Top guest favorite

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

5.0 out of 5 average rating, 39 reviews

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.

ValueFamilyPets

Superhost

A single-story home with a brick facade is presented. The driveway leads to a garage, while a well-maintained lawn features neatly trimmed grass and colorful flowerbeds. Large front windows allow for natural light, framed by light-colored siding underneath a gabled roof.

Home in Owensboro

4.94 out of 5 average rating, 141 reviews

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.

FamilyLocationAccess

Top guest favorite

Cabin in Dixon

4.96 out of 5 average rating, 346 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.

LocationFamilyQuiet

Top guest favorite

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

4.95 out of 5 average rating, 20 reviews

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.

FamilyLocationComfort

Superhost

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

5.0 out of 5 average rating, 17 reviews

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!

FamilyLocationCleanliness

Top guest favorite

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

4.99 out of 5 average rating, 198 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.

LocationFamilyCheckout

Top guest favorite

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

4.91 out of 5 average rating, 556 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.

LocationValueHeating

Top 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

4.93 out of 5 average rating, 46 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! Calhoun boat ramp is only 2 miles away. This property is centrally located, 25 miles north-east of Madisonville, 20 miles south of Owensboro.

LocationValueNearby

Superhost

Home in Livermore

5.0 out of 5 average rating, 4 reviews

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.

ComfortPetsSleep quality

Top guest favorite

Cottage in Owensboro

4.97 out of 5 average rating, 434 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.

LocationValueComfort