Holiday houses in Glenwood

Historic Drees Haus, Oldenburg

Drees Haus is a charming 1870s home on the historic district walking tour of Oldenburg. Located on a quiet street, across the street from the convent wall, and next to the well-maintained village park, this brick cottage home is an example of the town's late 19th century architectural style. It reflects the German heritage of the village, with much of the artwork and furniture original to the town and surrounding area. Easy walking distance to restaurants, shops, and the Catholic church

The Hidden Gem

It's rare to find a place that's both historic and one-of-a-kind. This 2nd story downtown spacious 4 bedroom, 4 bath offers more than just a place to rest your head. With off street parking and private stairway entrance,enjoy the community/living room where you can sit at the personal bar while playing pool, foosball or a game of chess with your guest. Every room is equipped with large smart TVs with access to all of your favorite streaming services. Multiple food options within walking distance

Spacious 3 Bedroom Home - New Castle

This home is equipped with everything you need for a relaxing stay. Unwind in the living room while watching your 65” TV. Prepare a meal in the fully equipped kitchen. The home offers a King, Full, and 2 Twin size beds. All 3 bedrooms are fitted with room darkening curtains. If you need a quick start, grab a shot of espresso on the way out the door. For a slow morning, pour yourself a cup of coffee and relax on the large back deck. The fully equipped laundry area offers washer, dryer, and iron.

NEW - Conner's Villa, Indoor Pool, Fire-pit, Golf

Welcome to our serene 4-bedroom haven near the golf course! Inside, discover a refreshing indoor swimming pool surrounded by ample space to lounge. Enjoy entertainment on multiple large screen TVs, enjoy time around the fire pit outside, or brew coffee at the bar. Relax in the fully stocked kitchen and spacious living areas. Play games in the game room, which also offers extra sleeping space. With 2.5 baths and laundry area, your comfort is ensured. Dive into fun and relaxation at our retreat!

The Lucky One; Cozy 3 bed 2 bath in Connersville

Relax in comfort at this newly updated and thoughtfully designed cozy home, located in the heart of Connersville. Perfect for families, couples, business travelers, and anyone looking for a peaceful stay near local attractions such as Arbor Crossing Golf Club, Brookville lake, scenic state parks, and charming small-town vibes. Step inside and experience a bright, clean, and modern space filled with amenities for everyone. Your stay will including a private drive, garage, yard games, and more.

Secluded Wooded Getaway w/ 2BR 2BA + Private Lake

Enjoy a weekend getaway at this cozy homestead nestled on 40 acres of wooded land with biking, hiking, walking trails and its very own stocked private lake & pedal boat. Take a break and relax on the dock or by the fire pit as you & your family & friends go off the grid... take a short drive to the quaint downtown Brookville, go experience the beautiful Brookville Lake & golf course, even check out the Wolf Habitat & Canoe Rental location right down the road. This is just the escape you need!

Tree City Retreat

Tree City Retreat is a cozy 3 bedroom, 2.5 bath home made to entertain any group. Relax with the whole family at this hidden gem located in Greensburg, IN, which is conveniently 1 hour away from Indianapolis and Cincinnati. Enjoy the outdoors with a pool, fire pit, pond, walking trail, badminton, basketball, game room, and many other outdoor games. Inside, make yourself a drink at the home bar and hang out with friends in the living room where you can take in the scenic view of the pond.

Backyard Barndominium

This memorable place is anything but ordinary. We’re a mile from I74 exit. This is a 2000 square foot house with a great room that towers to 14’ ceilings. Two large bedrooms with large walk in closets for extra dressing space. View from kitchen windows overlooks a forest of 100 trees. (And we’re in town!) Fully furnished kitchen to prepare your meals. You’ll find a beautiful park across the road with miles of wooded walking trails and a lot to explore. Lots of parking. Easy access.

Private Suite Sleeps 4 - Weathered Fence Post

Enjoy your stay in a private suite on spacious property at our farmhouse nestled amidst picturesque covered bridges, vintage round barns, and Amish charm. Relax on the deck and soak in the peaceful surroundings, take a stroll around the flower gardens, or unwind in the hot tub. It's beautiful, it's peaceful, it's safe, it's private! Book your stay today and experience the tranquility of rural America.

Grand Ave House in Connersville

Enjoy a stylish experience at this centrally-located home in Connersville. Located near shopping and restaurants, Roberts Park is within walking distance. 2 bed, 1-1/2 bath home with a large dining room and living room with workspace. Bathroom has a nice jacuzzi tub. Cheerful kitchen is stocked with major appliances and cooking necessities. Enclosed front porch to exercise or relax.

Cottage on the Bloom/Brookville Lake

Cabin on Brookville lake within a quiet neighborhood. Within a two minute walk of Brookville Lake and boat launch, find yourself inside this cabin with friends and family. This property offers a quiet and relaxed setting with many local attractions and activities. Four bedrooms, two bathrooms, a sun room with games, and large open area to take a break from the race of life.

Yellow House on the Hill Country Retreat

This quiet oasis in the country is perfect for family gatherings, small events, or a productive place to focus on work. The house is perched on a hill outside of town, providing a scenic overlook of rolling hills. Enjoy the sunrise on the front porch, and watch the sunset on the back patio. There is year round fun with sledding in the winter and barbecuing in the summer.