
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.

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

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.

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.

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!

Little Monticello
Little Monticello is a spacious 3 bedroom home one block away from the beautiful river front. Great walking paths. Walking distance to downtown Newburgh dining and shops. The master bedroom has a king size bed , bedroom # 2 has a queen size bed and dressing table. Bedroom #4 has a full size bed.. Bedrooms 1&2 have TV’s in them. The side porch is great for relaxing or hanging out with the little ones. There is a full size washer and dryer located in the kitchen area behind the barn door.

The Angel Carriage House in New Harmony
Cozy and elegant, located in the heart of historic New Harmony, this 1920's carriage house was reimagined, expanded, and tastefully furnished as a stand-alone guest house in 2016. It includes a fully equipped kitchen, roomy bedroom plus queen-sized sofa bed in the living room, two full baths, hi-speed WIFI, three HD TVs, a private back porch with one of the best views in New Harmony, and heated & A/Ced garage. Relax and recharge, just one or two blocks from the town's key attractions.

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!

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.

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.

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.

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.

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.
Popular amenities for Henderson holiday rentals
Other great holiday rentals in Henderson

Suburban Chateau

The Nest - Huge Loft in Downtown Henderson

Lakeside Log Cabin: Venue • Hunting • Fishing

Newly Listed! Secluded 3 BR house in the Woods!

Nature Lovers Retreat

Little House on the River

Nest: 1905 Carriage House Apartment

Victorian 1 Bedroom Guesthouse Apt on 1st Street
When is the best time to visit Henderson?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $135 SGD | $140 SGD | $163 SGD | $191 SGD | $177 SGD | $162 SGD | $154 SGD | $176 SGD | $159 SGD | $134 SGD | $134 SGD | $130 SGD |
| Avg. temp | 1°C | 3°C | 8°C | 14°C | 19°C | 24°C | 26°C | 25°C | 21°C | 15°C | 8°C | 3°C |
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 $110 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 $39 SGD per night before taxes and fees

Verified guest reviews
Over 470 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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