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
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
4.85 out of 5 average rating, 218 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!

Guest favorite
A comfortable living area is showcased with a spacious gray sofa adorned with blue and green cushions. A round wooden coffee table is centered on a large area rug. Two tall windows allow natural light to fill the space, complemented by a small dining table and chair.
Bungalow in Evansville
4.89 out of 5 average rating, 400 reviews

Fabulous on Historic First St. Near Haynies Corner

Light and airy with 11ft ceilings and warm wood floors, this 900 sq foot updated downtown 1 bedroom is just right for your next visit to Evansville. Whether you are in town for work or for play, this is a great spot for you. Located in the same block as Haynies Corner, two blocks from the river trail, and very close to Main Street, Ford Center and Old National events Plaza this home provides a great spot for the active life as well as the night life. Fully equipped, stainless appliances.

Top guest favorite
The exterior of the cottage showcases a welcoming blue facade with white trim. A covered porch features a comfortable swing, and large windows provide ample natural light. Lush green trees frame the peaceful setting, enhancing the cottage's serene ambiance.
Home in Henderson
5 out of 5 average rating, 39 reviews

Little House on the River

This gem is nestled on the riverbank, offering you a tranquil getaway with stunning water views and quiet surroundings. Our cozy cottage is perfect for couples or solo adventurers. You'll enjoy a blend of rustic charm and contemporary amenities. The open-concept living area features large windows that flood the space with natural light, offering uninterrupted views of the river. Situated on a peaceful, dead end street and just a short drive to local attractions, shops, and restaurants.

Guest favorite
A charming restored 1938 home features a light green exterior and a welcoming front porch. A white picket fence outlines the property, providing a quaint boundary. Two large windows adorn the upper level, and a simple decorative wreath accents the front door.
Home in Newburgh
4.84 out of 5 average rating, 431 reviews

Historic Downtown Newburgh

Restored 1938 home with original oak floors. You will have this sunny and homey house all to yourself. We have WiFi. It is in a very quiet neighborhood and only 3 blocks from the Ohio River and the River Walk. There are a couple of restaurants that overlook the river and within walking distance. We have plenty of grocery stores, pharmacies, gas, a theatre and only 10 minutes from the east side of Evansville. Newburgh is a great walking town with historical houses and civil war history.

Top guest favorite
The entrance features ornate wooden doors with intricate carvings and lace curtains visible through the glass. Large urns filled with colorful flowers flank the doorway, adding vibrant touches to the entry. A decorative doormat lies at the base of the steps.
Apartment in Evansville
4.99 out of 5 average rating, 399 reviews

Historic Home Apt B: 3 Blks to Haynie's Corner

Location, location, location! This 1BR/1BA apartment has all the perks and pampering of a hotel, but in a fully furnished private luxury residence. Our 1850 home is located in downtown Evansville on coveted First Street. This architecturally diverse street is filled with historic mansions, giving it character that is unmatched in any other neighborhood in Evansville. Guests will have the privilege of experiencing a unique atmosphere whether they are in town for business or leisure.

Top guest favorite
A wooden door with multiple panes opens into a cozy sitting area. Outdoor seating is provided by a small table and two chairs on a gravel patio. Natural light filters through the door, highlighting the inviting interior and lush greenery outside.
Guesthouse in Evansville
4.9 out of 5 average rating, 652 reviews

Nest: 1905 Carriage House Apartment

Our renovated 1912 carriage house was designed exclusively for Airbnb guests! Set in the midst of Semper Fulgens gardens, this luxury apartment is small but features a large bathroom with clawfoot tub, a loft bedroom with king sized bed, a sitting area, and coffee bar. There is not a full kitchen, but we do have a fridge. Not suitable for kids. A place for pet lovers! We do have two dogs, a cat and chickens who live on the property and have access to courtyard and event space.

Guest favorite
Home in Evansville
5 out of 5 average rating, 7 reviews

Fire Pit + BBQ + Private Yard 1BR Retreat

Enjoy your own private retreat in this stylish 1BR, 1BA guesthouse—fully separated and fenced for comfort and privacy. Ideal for solo travelers or couples, it features a comfy queen bed, full kitchen, fast Wi-Fi, and modern touches throughout. Step outside to your private yard with a BBQ grill and fire pit—perfect for relaxing nights under the warm string lights. Located in a quiet area, yet minutes from great food, shops, and local attractions. A cozy, secure getaway you’ll love.

Top 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, 221 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
4.98 out of 5 average rating, 66 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
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
4.98 out of 5 average rating, 331 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. 2 complimentary drip coffees are included with your stay.

Guest favorite
An indoor pool area features a long, narrow pool, surrounded by large windows that allow natural light to fill the space. The tiled floor is complemented by potted plants, and wicker chairs with cushions are arranged nearby for seating.
Vacation home in Evansville
4.94 out of 5 average rating, 189 reviews

Nugent House

It's rare to find a place that's both historic and one-of-a-kind. Whole house to enjoy in downtown Evansville Indiana. Walking distance to arts district , bars , restaurants, casino , ford center , Evansville museum, Evansville riverfront and much more.,, Home was built in 1915 as a mansion by the Nugent family. No lifeguard on duty, swim at your own risk

Guest favorite
Guesthouse in Henderson
4.89 out of 5 average rating, 84 reviews

Downtown 1 bed & 1 bath studio guest house

Enjoy easy walkable access to downtown Henderson festivals, restaurants, and river fun when you stay in our guest house. This one-bedroom 1 bathroom studio space has a private entrance, free parking, and access to an outdoor deck with seating Enjoy ammenities such as a queen-size mattress, 50" smart tv, full-size refrigerator, blow dryer, Keurig, and more.

Popular amenities for Henderson County vacation rentals