Holiday rentals in Glenwood

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

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!

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!

The Next Door Suite

If you ever wanted to book an overnight stay in downtown Laurel, Indiana...we got you covered! Our fully furnished 700 sq. ft. rental is literally steps from the historic Long Branch Tavern, a quarter mile from Haspin Acres and 6 miles from Metamora, Indiana. It features a full kitchen, living room, dining area, private bedroom with full size bed, 2nd private sleeping area with fold out bed, a common area with a futon, 2 twin beds, bathroom, shower, and can comfortably sleep up to 6 people.

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.

Monét Garden Suite • Breakfast • Antique Alley

Experience our restored historic 1888 bank in your private Garden Suite, inspired by Monet's ‘The Garden at Argenteuil.’ This boutique retreat blends art, music, and English-country charm right on Main Street, in the heart of Indiana's Antique Alley. Sleeping up to 7 guests, the spacious suite offers a full kitchen, living room, dining room, and bath. Wake to complimentary artisan pastries, house-made granola, and Nespresso, fresh flowers in summer months, and a vinyl record collection.

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.

5BR Retreat w/ Private Indoor Pool In Greensburg

Welcome to your perfect getaway in Greensburg, Indiana — a spacious and beautifully designed 5-bedroom 2 1/2-bath home featuring a private indoor pool for year-round relaxation and fun. Whether you're visiting for a family trip, weekend escape, or extended stay, this home offers the ideal blend of comfort, entertainment, and convenience — all just about an hour from Indianapolis and Cincinnati.

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.

Seven Springs Hideaway

Nestled in the rolling hills of rural Franklin County, Laurel, Indiana awaits the perfect place to escape the busyness of life. Whether it is a family reunion, staff outing or a friend trip, this spacious home, property and pond provide the ideal getaway. You will have full use of the three story home, the 18 secluded acres, and the pond.