Vacation rentals in Henderson County

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Top-rated vacation rentals in Henderson County

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

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Guest favorite

A welcoming living area features a comfortable sectional sofa adorned with decorative pillows. A sleek coffee table occupies the center, while a modern television is positioned across from the seating. Soft lighting is provided by a ceiling fan, and large windows dressed in dark curtains allow natural light.

Home in Evansville

4.94 out of 5 average rating, 138 reviews

House Near U of Evansville and Ford Center

Stay at this peaceful and centrally located home with fenced yard. The house has been completely remodeled and is located 5 blocks from the University of Evansville and 7 minutes from downtown Evansville for concerts, shows and conventions. The house is located in a quiet safe neighborhood and is 15 minutes from anywhere in town. The house has 2 bedrooms, each with a queen bed, sleeping 4 total. One queen bed has an adjustable base to adjust head and legs in various positions for maximum comfort

Top guest favorite

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

4.88 out of 5 average rating, 267 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 favorite

The exterior of the Hobbit House features unique architectural elements, including curved rooflines and a distinctive round window. A manicured pathway leads to the front door, with greenery surrounding the entrance and decorative outdoor lighting providing subtle illumination.

Home in Evansville

4.97 out of 5 average rating, 119 reviews

Hobbit House 2 bedroom.

Welcome to the Hobbit House! Relax or work from home in this cozy house located in a charming, quiet neighborhood in central Evansville. Each room is curated to set a different vibe from relaxation, sophistication, and fun. This house also has an old speakeasy downstairs filled with arcade games and a movie projector and screen. At night relax in the backyard under a beautifully lit gazebo. This house is also equipped with an office set up to make it easy to work from your home away from home.

Guest favorite

A spacious living area features a comfortable gray sofa complemented by two armchairs, one adorned with a decorative pillow. Natural light enters through large windows, illuminating the warm wood floors. A side table and lamp provide additional lighting in the inviting space.

Home in Newburgh

4.81 out of 5 average rating, 101 reviews

Pecan Place near Newburgh Evansville and Kentucky

Pecan Place has all the tranquility of the country with all the amenities of the city. A warm, cozy ranch home with open plan. Sitting on 2.5 acres of beautiful fields & shade of pecan trees. It is just right for relaxing & enjoying each other's company. In town for work or play, it is a great spot to find peace and quiet after a long day. Located near downtown historic Newburgh, Evansville and Henderson Kentucky. This home provides the perfect spot to enjoy all three cities have to offer.

Top guest favorite

A welcoming front porch features a comfortable seating area with two blue chairs, adorned with decorative pillows. A small side table is positioned next to a larger wicker chair, and the view includes lush greenery and tranquil neighborhood streets.

Bungalow in Evansville

4.92 out of 5 average rating, 144 reviews

Cozy Craftsman in Akin Park Neighborhood

This cozy craftsman style home is nestled in the Akin Park neighborhood and includes all the amenities needed for a great visit to Evansville. The location boasts quick access to Haynie’s Corner/Art District, which features unique shops, bars and restaurants that showcase the best of Evansville culture. You are welcome to cozy sleeping arrangements for up to six (two queen bedrooms and a pull out couch), one bathroom, a fully stocked kitchen and a beautiful front porch perfect for relaxing.

Top guest favorite

A cozy living area features a brown leather sofa paired with a plush cream-colored armchair. A large patterned rug anchors the space, while a wooden coffee table provides a functional centerpiece. An acoustic guitar leans against the armchair, adding a creative touch.

Home in Evansville

4.98 out of 5 average rating, 289 reviews

Haynie's Hangout

Haynie’s Hangout was featured in Evansville Living. Located in the Art's District and within walking distance of restaurants. Ideal for business travel. Spacious desk for work needs. Very close to downtown attractions. Charming two bedroom shotgun home with stylish and hip decor. All bedding is high quality. Cozy living room with large smart TV/LG and internet access for Netflix, etc. Leaf antenna provides local TV channel access. Equipped kitchen! Washer/Dryer. Patio! Photo ID required.

Top guest favorite

The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.

Loft in Newburgh

4.97 out of 5 average rating, 422 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

Top guest favorite

The interior showcases a warm, wooden design with vaulted ceilings and exposed beams. A modern television is mounted on the wall above a stone fireplace, while a cozy seating area is arranged with a dark sofa and wooden coffee table. The space is well-lit and inviting.

Cabin in Corydon

4.96 out of 5 average rating, 134 reviews

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.

Guest favorite

The cabin is showcased with a modern architectural design, featuring a wooden facade and large windows that allow for natural light. The structure sits on a grassy area, with a clear blue sky enhancing the overall appearance.

Cabin in Robards

4.93 out of 5 average rating, 127 reviews

REINE CABIN at Farmer and Frenchman

EAT. TASTE. STAY. Year round view, seasonal flavor. The property features a winery/cafe, a vineyard, walking trails, and a 360 view of countryside. Created in the spirit of rustic elegance, the Cabin's lavish accents are sure to impress. Enjoy dinner in the cafe, walk the trails, snuggle in for the night, order breakfast in bed and a morning yoga session on the patio. Enjoy the ambiance of Kentucky's agrarian heritage with modern and stylish amenities.

Guest favorite

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, 274 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.

Top guest favorite

An open living area features large windows that allow natural light to fill the space. A comfortable sofa and patterned chair are arranged around a central area rug. A wooden table and chairs are positioned nearby, offering additional seating options.

Loft in Henderson

4.99 out of 5 average rating, 105 reviews

The Lifeboat Loft - in the Heart of Henderson

Welcome to The Lifeboat Loft, our luxury apartment in Downtown Henderson KY! This unique 1100 sq ft loft on Main Street features soaring ceilings, a comfy king bed, upscale furnishings, a fully equipped kitchen, washer/dryer, high speed WiFi and a cool rolltop desk work area. 7 restaurants and the Vault venue are within 1 block. The new couch features a hideaway bed for extra company. It’s even friendly to your furry friends!

Top guest favorite

A charming yellow cottage is presented, featuring a well-maintained front yard with green grass. The exterior includes white shutters and a welcoming front door. An American flag gently waves, and a single-car garage is visible on the left side.

Cottage in Newburgh

5 out of 5 average rating, 155 reviews

Newburgh Yellow Comfy Cottage

The Newburgh Yellow Comfy Cottage is a quiet retreat located near the Newburgh Rivertown Trail and Ohio River just minutes away from quaint shops, restaurants and scenic views. Health enthusiasts will enjoy walking, running and/or riding bicycles on the trail. Great for business travelers, vacationers, or out-of-town visitors. There are two bedrooms with one equipped as an office space.