Holiday rentals with a patio in Henderson County

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.

The Nest - Huge Loft in Downtown Henderson

Welcome to The Nest, Henderson's finest loft! This Victorian 1800 sq. ft. loft is newly renovated, fully furnished and nicely appointed in the heart of Downtown Henderson. The huge living room is perfect to meet friends, watch TV, cook, or just gaze out the massive windows. The Master Room, Reading Room (featuring a queen Murphy bed), fully equipped Kitchen, and Private Patio are quiet spaces to relax, work, prepare a meal, or plan your day. Parking, fast wifi, and washer/dryer all included!

The Cypress Cottage

Pickleball anyone? Looking for a quiet place to disconnect and unwind? You’ll love this 1878 cottage getaway. With 4 bedrooms, there is plenty of room for you to kickback and relax. Cook a meal in the full kitchen and step outside and play pickleball on the private, woods surrounded court. Washer and dryer are included at this country getaway. A short drive to historic New Harmony and Evansville so you can attend events like Kunstfest and the Fall Festival. Also not far from USI & U of E.

House of Color A | KING 1BD/1BA Apt near Downtown

Enjoy this stylish and fully renovated one-bedroom, one-bathroom apartment in close proximity to Evansville’s Art District (Haynie’s Corner) and Downtown EVV — perfect for a weekend escape or a longer stay. ✅ Sparkling Clean ✨ ✅ King Bed for ultimate comfort 🛏️ ✅ Fast WiFi 🚀 ✅ Smart TV in the living room 📺 ✅ Stocked Kitchen for easy meal prep 🍽️ ✅ Washer and Dryer in Unit 🧺 ✅ Free Street Parking 🚗 ✅ Fabulous Location near local art, dining, and attractions 🎨🌆

Pink House in Historic Arts District

Step back in time in this spacious 1890s Victorian located in Evansville's historic district walking distance to museums, waterfront parks and Haynie's Corner Arts district with it's cozy cocktail bars and restaurants. Ford and Old National event centers, Victory Theatre and historic Main Street are 5 min drive or 20 min walk. Lovingly restored over four years, you'll experience original Queen Anne details paired with modern touches and eclectic decor.

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.

Quiet Cottage

Relax at this peaceful home that only takes 5 mins. to get to Evansville’s downtown! Enjoy an outdoor sitting area and parking your car safely in our oversized two car garage. •Always thoroughly cleaned ✔️ •Extra amenities provided: coffee, bathroom necessities ✔️ •Comfortable beds ✔️ •Kid-friendly: crib, high chair, toys, blow-up house✔️ •Host lives close by and is readily available and always happy to help ✔️

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.

The Zen Den - Dog friendly! NO cleaning fee!

Find your zen at this peaceful and centrally-located space. Upstairs apartment with private entrance & off-street parking. Relax from a long day in the tub, cozy king bed, or on the spacious balcony. Yoga equipment provided to help clear your mind from the daily stresses of life. Lots of local touches to connect you to artists & artisans of the area. Your home away from home.