Holiday rentals in Henderson

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Top-rated holiday rentals in Henderson

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

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Guest favourite
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, 116 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 favourite
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, 107 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.

Top guest favourite
A view from above captures a six-person hot tub with inviting blue water. Nearby, a circle of Adirondack chairs surrounds a fire pit, all nestled in a wooded area illuminated by warm string lights hanging overhead.
Cabin in Eckerty
4.98 out of 5 average rating, 155 reviews

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

Guest favourite
A contemporary living area features two patterned armchairs beside a small round table with a decorative lamp. Abstract artwork adorns the brick wall, while a textured rug adds comfort underfoot. Soft, ambient light enhances the inviting space.
Loft in Evansville
4.97 out of 5 average rating, 118 reviews

The Cooper I on Franklin (The Ashby Collection)

Right in the heart of Franklin Street! All the “city feels” in this contemporary walk up loft! We provide all the pleasures, perks and pampering of a hotel, but in a fully-furnished private luxury residence. Just steps away from incredible restaurants, bars, pubs, live music, and specialty boutiques. Once you’ve arrived at The Cooper, grab a seat at our window bar overlooking Historic Franklin Street! We have equipped you with everything from a well appointed kitchen to a fabulous hot tub!

Top guest favourite
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, 384 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 favourite
Cabin in Dixon
4.96 out of 5 average rating, 329 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 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, 534 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 favourite
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, 125 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 favourite
Cottage in Owensboro
4.97 out of 5 average rating, 419 reviews

Nature Lovers Retreat

This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

Top guest favourite
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, 223 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 favourite
Guest suite in Evansville
4.82 out of 5 average rating, 268 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.

Superhost
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.
Holiday home in Evansville
4.94 out of 5 average rating, 200 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

Popular amenities for Henderson holiday rentals

When is the best time to visit Henderson?

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Frequently Asked Questions

  • 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.

  • 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 $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • Are there vacation rentals with a dedicated workspace in Henderson?

    Yes! Work meets play with ease at over 20 vacation rentals in Henderson featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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.

  • 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.

  • 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.

Quick stats about holiday rentals in Henderson

  • Total holiday rentals

    Explore 30 holiday rentals in Henderson

  • Nightly prices starting at

    Henderson holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 520 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Henderson holiday rentals include wifi 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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