Holiday houses in Osceola

Choo Choo Inn

Discover the perfect pet-friendly haven in the heart of Elkhart County! This charming home is your ideal destination for a serene and rejuvenating getaway. Situated near the third-largest rail freight yard in the U.S., you'll love the unique train-themed ambiance. While you unwind on the deck, keep an eye out for graceful deer and enjoy the soothing sounds of trains rolling by. Plus, there’s ample parking available for RVs, making it a great choice for those is in town for a service call.

Cozy "DOG friendly" cottage

Keep it simple at this peaceful and centrally-located place. Enjoy this 704-square-foot, 100-year-old home. We've remodeled "almost the entire house to satisfy anyone looking for a cozy, quiet stay. Perfect for a business trip or a family vacation of up to 4. Close to the Mishawaka river walk and a public golf course. We did mention we are "dog friendly", Right? Bring your Well "behaved" pup they will definitely enjoy the fenced-in yard, it is sure to keep you and your best friend happy.

Treehouse Acres

Treehouse Acres, a Treehouse style retreat nestled on 10 acres of woods near Baugo Park. This unique home offers king bed, hot tub, air hockey, fire pit, outdoor area and walking trails right to Baugo, ensuring a blend of relaxation and adventure. With 3 bedrooms, 1.5 bathrooms, and a pullout couch, it comfortably sleeps 7 Perfect for family getaways or catch a Notre Dame game, enjoy all the comforts of home, including a full kitchen and laundry, in a secluded yet convenient location

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

The Serenity Suite

The Serenity Suite is one of two listings to accommodate guests. This suite is a 230 sq ft. tiny house studio apartment created in 2022. A kitchen island with 2 barstools is in the center of the space. This can be used as a sit down eating spot or a dedicated workspace. The 3/4 bath boasts up to date accessories and soft, thirsty towels. Please check out our Whispering Pines listing for a more spacious area. It will accommodate 1-5 guests at a very competitive price.

Relaxing Riverfront House • Dock Access • Sleeps 6

Stay in our modern riverfront 2‑bedroom home with a private dock! ✔ Direct riverfront access with private dock ✔ Updated, comfortable home with modern touches ✔ Sleeps 6 with 2 queen beds, sleeper sofa & floor mattress ✔ Full kitchen with quality appliances ✔ Reliable WiFi for work or streaming ✔ Professionally cleaned and sanitized ✔ Peaceful setting perfect for fishing, kayaking & relaxing ✔ Great for families, couples, and quiet getaways

Cozy family friendly oasis |4 BR |River views|ND

Pack your bags and bring the whole crew! This stunning 4-bed, 2-bath retreat offers serene river and channel views in a safe, welcoming neighborhood. Grill outdoors, whip up meals in a fully equipped kitchen, and binge your favorites in spacious lounging areas. From river view evening walks, outside campfires and s’mores under the lights, stars to late-night card games, adventure and relaxation await. Great dining and a hospital close by!

The Boho Bungalow

The Boho Bungalow is an updated 1920's bungalow with plenty of traditional charm. Wood floors, built ins and vintage kitchen make it cozy and welcoming. It's perfect for traveling professionals or families needing short term housing while visiting the Elkhart/South Bend area. The home is just blocks from Elkhart General Hospital and is very convenient to downtown Elkhart, Granger and South Bend. It's less than 15 miles from Notre Dame.

Silk On the Bend

My place is close to 80/90 Toll -road exit 83-Mishawaka IN. Visit us for events at :Notre Dame/St. Mary's/Bethel college/Holy Cross College. Mileage to ND Campus is 11.4. 15 Minutes to Elkhart Aquatic Center. Approx 20 Min to Four Winds Casino (Via the 20 Bi-pass) This Spring 2021 The Silk was chosen by AIRBNB as the 2d best place to stay in the greater South Bend-Mishawaka area. I close in January and February but re-open in March.

Luxury 6BR Summer Retreat | Pools + Sports Court

Just 15 mins to Notre Dame and 1 hour to Indiana Dunes! Perfect for an end-of-summer break with late August availability. This private 1.5-acre estate sleeps 16 and features a heated indoor pool, outdoor pool, and rare indoor sports court. Enjoy resort-style living near Mishawaka dining, the St. Joseph River, and Granger shopping. Secluded, upscale, and optimized for families, teams, or reunions. Book your Indiana getaway today!

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Little House On The River

Escape to the Little House On The River in Elkhart, IN! This cozy 1-bedroom, 1-bath retreat sleeps 4 and offers stunning river views, a private deck, and all the comforts of home. Just 30 minutes from Notre Dame and a short drive to Shipshewana, it’s the perfect spot for game days, Amish country exploring, or simply relaxing by the water. Peaceful, private, and unforgettable—your riverside getaway awaits!