Vacation rentals in Henderson

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Top-rated vacation rentals in Henderson

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
4.96 out of 5 average rating, 99 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

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
4.87 out of 5 average rating, 240 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
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, 271 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, 353 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
Cabin in Dixon
4.96 out of 5 average rating, 317 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.

Top guest favorite
An open-concept living area is highlighted by exposed brick walls and wooden flooring. A comfortable seating arrangement includes a sofa and two chairs, inviting relaxation. The kitchen features modern appliances and a breakfast bar with stools, with natural light streaming through large windows.
Home in Downtown Evansville
4.93 out of 5 average rating, 105 reviews

Downtown Haven Retreat

Welcome to the Dr. J.R. Mitchell House! Built in 1909 as what is believed to be the first animal clinic in Evansville, this century-old home has been renovated and modernized. This downstairs apartment was Dr. Mitchell’s original animal clinic while his family’s quarters was located upstairs. Inside, you’ll discover urban comfort at our 2 bed, 2 bath apartment and be just steps away from shopping, dining, and all that the downtown riverfront area has to offer.

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, 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.

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
4.94 out of 5 average rating, 124 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, 234 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 favorite
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, 101 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 favorite
A cozy living area features a comfortable sofa with decorative pillows and a welcoming atmosphere. A coffee table is centered beneath a tasteful arrangement of candles and plants. Warm lighting is provided by two side tables with lamps. A front door with an oval window adds charm.
Home in Corydon
4.96 out of 5 average rating, 219 reviews

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.

Guest favorite
A white single-story house is framed by lush green landscaping. Two windows with gray shutters are visible on either side of the front door, which is painted in teal. A pathway leads to the entrance, surrounded by tall grass and leafy plants.
Apartment in Evansville
4.78 out of 5 average rating, 347 reviews

Best Value/Sleeps 4/ Cozy/Center Town /Pets ok!

This is a private unit, but There is a GUEST SUITE attached to this listing (also available on Air BNB.) However, there are NO shared spaces. Each listing has a separate entrance. Near shopping, restaurants. 1Bedroom-2 queen beds-1bath cable/wifi, stocked wi/ snacks & amenities. Key lock box entry, Washer/Dryer. Couch folds down with a pull out feature on the base see pics or contact us to operate.

Popular amenities for Henderson vacation rentals

When is the best time to visit Henderson?

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Frequently Asked Questions

  • What are the most popular amenities for Boutique Hotel Rentals in Henderson?

    Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do boutique hotel rentals in Henderson have air conditioning?

    Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Henderson. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Henderson have wifi?

    Absolutely! We offer over 10 boutique hotel rentals with wifi in Henderson. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Henderson?

    Four-legged friends are welcome in Henderson. Choose from more than 10 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in boutique hotel rentals in Henderson?

    Experience the best of Henderson with our boutique hotel rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there boutique hotel rentals with a dedicated workspace in Henderson?

    Yes! Work meets play with ease at over 10 boutique hotel rentals in Henderson featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Henderson?

    Henderson has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do boutique hotel rentals in Henderson have free parking?

    Absolutely! We offer over 10 boutique hotel rentals with free parking in Henderson. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Henderson

  • Total vacation rentals

    Explore 30 vacation rentals in Henderson

  • Nightly prices starting at

    Henderson vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 470 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Henderson vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Henderson rentals

  • 4.6 Average rating

    Henderson stays receive an average rating of 4.6 out of 5 from guests

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