Vacation 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

Family · Location · Cleanliness

New-Honeymoon Suite-Hot Tub-Sauna-Romantic Getaway

Escape to Liv’s Treehouse- a magical honeymoon suite in the heart of Indiana's rolling hills! Although a treehouse, only 4 steps to it! Enjoy a private hot tub, sauna/steam room, stunning scenic views,patio and flat-top grill. The fully-equipped kitchen, double-ended tub, and a king-sized bed with beautiful views, offer both comfort and luxury. Guests are invited to mingle with friendly farm animals for a unique experience. Enjoy the convenience of self check-in in this serene woodland hideaway.

Location · Condition · Comfort

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!

Value · Family · Backyard

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!

Location · Family · Laundry

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.

Family · Value · Indoor spaces

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.

Family · Location · Breakfast

The Camp in Oxford (OH)

The Camp in Oxford includes3 private acres nestled right alongside the Indian Creek River and surrounded by sprawling farmland. Located just 5 miles from Miami University, 13 miles from Brookville Lake and short drives to Hamilton, Cincinnati or Dayton, this beautiful 2 bedroom modern cottage is waiting for your next visit. Fully furnished and equipped with every amenity you'd expect from a 5 star property.

Family · Location · Hospitality

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.

Location · Value · Kitchen

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.

Family · Location · Indoor spaces

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.

Location · Value · Hospitality

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.

Value · Location · Walkability

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.

Location · Value · TV