Holiday houses in Calhoun

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Top-rated holiday rentals in Calhoun

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The exterior of a single-story home features light gray vinyl siding and a dark gray roof. White window shutters complement the windows, and a covered porch is positioned at the entrance. A grassy lawn surrounds the house, with a clear sky and scattered clouds above.
Home in Owensboro
4.84 out of 5 average rating, 243 reviews

Emma B's Place Close to Town and the Riverfront

Emma B's Place is newly renovated and ready for guests! Here you'll find a cozy atmosphere, comfortable beds, fully equipped kitchen, and brand new washer & dryer. The location is convenient to an award winning Riverwalk, shopping, great dining, and our central location offers a short commute to the entire city. If you prefer to stay in and relax, a 42-inch smart tv and wireless high-speed internet are available for your enjoyment. Lockbox self-entry. Your hosts live nearby if you need anything!

Guest favourite
A sliding door opens onto a spacious deck, framed by a wrought iron screen. Outdoor seating is positioned on the deck, facing a green yard and trees, allowing for a serene view of nature.
Loft in Hartford
4.96 out of 5 average rating, 168 reviews

Cozy One Bedroom Apartment in the Country

What was originally a hay loft has been converted into a country chic barn apartment. We would love to host you and your friends and family (including actual kids and fur kids) on our property. Children love collecting eggs from the chicken coop and everyone loves a short hike to the creek. We are only an hour from Mammoth Cave National Park and an hour from Holiday World in Santa Claus Indiana. The local community has charming little shops, several restaurants, and The Beaver Dam amphitheater.

Top Guest favourite
An aerial view captures a serene swimming pool surrounded by a spacious patio. A separate guest house is visible near the pool, featuring a sloped roof and multiple windows. Lush landscaping offers privacy, while a clear pathway leads from the pool area to the nearby road.
Guesthouse in Evansville
4.87 out of 5 average rating, 247 reviews

Private Guest House close to everything!

The Private Guest House is set on our property which is located on a corner (1.5 acre lot) close to the east side of Evansville. The convenient large circle drive makes it easy to enter and exit. The east side of Evansville offers Malls, Shopping, Restaurants, Bars, Entertainment, Gyms, Starbucks, and Theaters. The property is located only 10 minutes from Downtown and the Ford Center due to close proximity to Lloyd Expressway. Check out the Casino and Riverfront if you’re in the Downtown Area!

Top Guest favourite
The exterior of a renovated two-story home is featured, showcasing a distinct architectural design with exposed beams. Large windows allow natural light to enter, while a welcoming front door is framed by decorative lighting fixtures. A concrete pathway leads to the entrance.
Cottage in Owensboro
4.97 out of 5 average rating, 159 reviews

The Woodford Retreat Cottage

Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

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
4.91 out of 5 average rating, 35 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! If you have a boat, the Calhoun boat ramp is only 2 miles away. This property is centrally located - 25 miles north-east of Madisonville, 20 miles south of Owensboro, Ky.

Top Guest favourite
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 out of 5 average rating, 181 reviews

4bed3BR Near Conv Ctr/Fisher Pk/30to HolidayWorld

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv, private Home is 3 miles from Convention center, River Park Center, Bluegrass Museum, Science Museum, Botanical Garden. It’s also minutes from baseball fields (Fischer) 30 min 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.

Top Guest favourite
Cabin in Dixon
4.96 out of 5 average rating, 319 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.

Guest favourite
The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.
Home in Owensboro
4.95 out of 5 average rating, 184 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
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, 527 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.

Top Guest favourite
A historic brick building stands on a cobblestone street, framed by mature trees and shrubs. The entrance features a set of stairs leading to double doors adorned with decorative glass. A lamppost adds charm to the inviting outdoor space.
Apartment in Evansville
4.95 out of 5 average rating, 238 reviews

Victorian 1 Bedroom Guesthouse Apt on 1st Street

This one-bedroom / one-bathroom apartment features high ceilings and exposed brick and is attached to your host’s home - a Victorian townhouse on one of Evansville’s historic cobblestone streets. Enjoy easy self-check-in and a location that is centrally located near the Ohio River, Downtown Evansville, and Haynie’s Corner neighborhoods. The Ford Center, Bally’s Casino, and many of Evansville’s best restaurants and bars are all a short walk away.

Guest favourite
A single-story home with a light blue exterior sits in a quiet neighborhood. The well-maintained front yard features small shrubs and landscaping, while a paved driveway provides easy access. Trees in the background showcase autumn colors, enhancing the peaceful environment.
Home in Evansville
4.87 out of 5 average rating, 102 reviews

Kozy Kathleen

*Currently listed as top 10 AirBnbs in Evansville, IN. *Kozy family home in a quite neighborhood with 2 car capacity drive way including street parking if necessary. *Full of amenities needed for any length of stay. Close to I-69 and HWY 41 for any travel requirements. *Less than 5 miles from the heart beat of Evansville (Ford center/ downtown/ and Eastland mall). *"The Kozy Kathleen" = Real Hoosier home with authentic mid-west feel.

Top Guest favourite
A tidy living room showcases a plush, purple sofa and a cozy armchair, accompanied by a decorative lamp and coffee table. A white fireplace serves as a focal point, while natural light filters through the window coverings, creating a welcoming ambiance.
Home in Owensboro
4.98 out of 5 average rating, 179 reviews

Granny Smith's

Granny Smith's is an endearing home in the heart of Owensboro, located in a historic neighborhood. The house features one sizable bedroom, tidy living room, full kitchen, cozy dining area, and a tub/shower bathroom. There is also relaxed outdoor living areas either on the front porch or back screened in patio. Property also has a small detached carport with a driveway. There is also parking on the street.

Popular amenities for Calhoun holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. McLean County
  5. Calhoun