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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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
4.86 out of 5 average rating, 222 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 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, 121 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, 265 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
A cozy living area is showcased, featuring a gray sofa adorned with patterned cushions. A wooden coffee table sits on a decorative rug, with a potted plant nearby. In the background, a partially visible kitchen area and art pieces add a touch of warmth to the space.
Home in Newburgh
4.97 out of 5 average rating, 104 reviews

RiverTown Retreat – Cozy 2BR Near River & Downtown

This is our personal home we use when lucky enough to be in the area. Our daughter married a sweet young man from here & we fell in love with this beautiful, friendly community and its adorable waterfront and downtown areas. We designed everything about this cottage to be exactly what we want & need, & we hope you appreciate all our thoughtful touches. Relax at this peaceful place to stay & enjoy Newburgh! Our location is also a great base for exploring Evansville, Owensboro, & Henderson.

Guest favorite
A serene lakeside view captures a quaint cabin reflected in calm waters. Lush green grass surrounds the water's edge, while trees frame the background under a blue sky dotted with clouds.
Cabin in Dixon
4.96 out of 5 average rating, 309 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
The front of the cottage features a welcoming dark blue exterior with a bright red door, flanked by well-maintained gardens. Potted plants and colorful flowers enhance the entrance, providing a charming first impression. A small walkway leads to the door, completing the inviting atmosphere.
Cottage in New Harmony
4.99 out of 5 average rating, 414 reviews

New Harmony Cottage

Open concept cottage w lots of space for one or two located in the Historic District of New Harmony. Free street parking, a sitting area and comfortable queen bed. Washer/Dryer and a small kitchenette (no stove or cooktop.) WiFi and and a Smart TV for your convenience. Bring your Netflix or Hulu passwords. Be our guest in your own space. Easy no contact checkin & checkout. Coffee/Tea bar or Black Lodge Coffee! *FYI check hours for shops & restaurants that you plan on visiting.

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, 520 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
4.93 out of 5 average rating, 123 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.

Top guest favorite
An open living area showcases original exposed brick walls and modern amenities. A spacious kitchen island is paired with stainless steel appliances. The living space features a sectional couch facing a large projector screen, with ambient lighting provided by pendant fixtures.
Home in Downtown Evansville
4.96 out of 5 average rating, 228 reviews

Rooftop Views in the Heart of Downtown!

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. Dr. Mitchell's owners' quarters above the original animal clinic now features two bedrooms, an open bunk room for kids, and three full bathrooms. You'll find the original exposed brick throughout the home which adds the perfect vibe to this modern industrial home.

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, 211 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
Guest suite in Evansville
4.82 out of 5 average rating, 259 reviews

Private Suite/Sleeps 3/Center Town/Pets OK!

Guests will have their own entrance and is closed off from the rest of the house. It is a 2 room space (250sf) Has a queen memory foam bed . A bathroom and a kitchenette in the next room (with microwave, coffee maker, mini fridge, panini press) fold down couch for 3rd guest You will get much more from us than a hotel room and much cheaper! Pet fees $20 per stay $5 guest fee per day after 2.

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, 334 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.

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 free parking, over 10 homes with air conditioning, 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 ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 440 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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