Holiday rentals in Middletown

Updated Historic Home, in the Heart of Greenfield

A one-of-a-kind historic gem located three blocks from Downtown Greenfield on Main Street and only a 35-minute drive to downtown Indianapolis. Enjoy the entire downstairs of this completely upgraded late 1800's wooden frame home featuring all original wood flooring and beautiful antique furniture pieces. Filled with modern luxuries; including 3 flat screen tv's with streaming services included, an upgraded 8 burner gas stove, dishwasher, full-size washer and dryer, and outdoor barbecue grill.

Enjoy Nostalgia In James Dean's Hometown

The Rebel Lodge is a fully restored historic brick building located in the heart of James Dean's hometown. lt is right across the street from the James Dean Museum, just around the corner from Main street, and only blocks from The James Dean Gallery. The building will sleep 4-5 with a comfy double bed, a pull out sofa and an additional sofa. It is decorated with fun mid century furniture and decor. Everything is freshly up to date with new furnace, & air conditioning. Please enjoy your stay!

The Cozy Cottage

Enjoy a relaxing getaway in this cozy cottage. Historic Downtown Noblesville is just a short walk where you will find great restaurants, pubs, and boutique shops. The cottage consists of one bedroom, a fully equipped kitchen, and a full bathroom with walk-in shower. There’s also a fenced backyard with fire pit and furniture. The Cozy Cottage is centrally located near downtown Noblesville (2 min), Ruoff Music Center (15 min), Grand Park Sporting Complex (20 min), and over 100 miles of trails.

🦉Wooded Suite Retreat - 2BR Easy i69 Access!

Recharge surrounded by nature in this cozy, comfortable, clean 2 BR “in-law” suite nestled among towering ash trees in a rural, wooded neighborhood just outside town near the White River. Enjoy the full private apt (2 BR, LR, kitchen, bath, washer & dryer) on lower level of host’s home. Great for singles, couples, families or work travelers. Near I-69, Anderson University, Hoosier Park, Mounds State Park, Rangeline Nature Preserve, Anderson Airport, St Vincent & Community Hospitals & more!

Entire Home with Modern Conveniences - New Castle

This home has been equipped with everything you need for a relaxing stay. Unwind in the evening while watching your 65” TV. The updated kitchen offers plenty of space for cooking dinner.The first bedroom features a King size bed and room darkening window treatments. The second bedroom offers a designated office space w/ high speed internet and a trundle bed. To start your day well, the bonus room offers a coffee bar with Nespresso and wellness area complete with treadmill and yoga space.

Quaint carriage house.

You’ll think you are in the country when you arrive at our peaceful 10 acre property right in Muncie. Located near our historic home, built in 1848, you’ll find a carriage house with an upstairs apartment with everything you need for a relaxing and comfortable stay. This is a quaint, rustic cabin like space with private outdoor area. You are only five to 10 minutes from BSU and IU Ball Hospital, downtown, Elm Street Brewing, the Children’s Museum, walking trails and most restaurants.

Designer 2 bedroom, 1 acre retreat in the city.

Welcome to the Honeysuckle Homestead. This is a completely updated 2 bedroom, 1.5 bathroom cottage with designer updated decor, nestled on a 1 acre wooded lot. Enjoy a peaceful morning on the trails or cooking a meal in a fully stocked kitchen. Adventure minutes away to Broadripple Avenue, Keystone Fashion Mall, Butler University, or a 15 minute drive to downtown Indianapolis. Quiet, safe neighborhood with ample parking and local ownership.

Anderson Art House-Entire house to yourself nearAU

We are located 0.3 miles from Anderson University, 1 mile from down town Paramount theatre. This is a house all to yourself with 3 bedrooms and 2 full baths. Each bedroom can sleep two plus additional two for the sofa bed in the living room. There is a small deck with a bbq grill when the weather is nice. This house will feature local artist's artwork through the house because there's so many talent in town we want to share with the world!

10 Min to Grand Park | Family-Friendly Quiet Area!

Nestled in a safe and beautiful neighborhood in the heart of Westfield, our home offers the perfect balance of peace and convenience. The area is quiet, welcoming, and ideal for unwinding after a full day of activities, yet close enough to everything you might want to explore during your stay. Tree-lined streets, friendly neighbors, and a calm atmosphere make this an ideal retreat for both short visits and longer stays.

White River Retreat

Escape to a private retreat on the White River in Indianapolis! This custom-built home offers a peaceful, open-concept space with a stone fireplace, pool table, and jetted tub. Enjoy 12 acres of shared grounds with river access, kayaks, and fire pits. Perfect for a unique getaway, feeling worlds away yet close to everything. Ideal for couples or small groups seeking tranquility and adventure.

Cozy cabin w/ pool, hot tub, gazebo & gardens

Our original log cabin with private pool (open Memorial Day-Oct. 1), hot tub and gardens provides the perfect get away! Located on Quaker Hill right next to a retreat center, you’ll have access to trails leading to a beautiful waterfall. The Historic Downtown and Depot Districts are both just a mile away or you can visit Earlham College or explore the Antique Alley nearby.

Studio M

Studio M is located in the small Historic town of Pendleton, IN. The home is within walking distance of our shops, restaurants and Falls Park. We have a fully stocked kitchen, car port with chairs to sit out and enjoy the beautiful outdoors. Our house is conveniently located to Fishers, Anderson, Noblesville and Indianapolis.