Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A sturdy wooden dining table is set with floral decorations and a colorful runner. Four wooden chairs are positioned around the table, while the kitchen's warm cabinetry and light-colored walls provide a welcoming atmosphere. Natural light brightens the space from a window above the sink.
Home in Mishawaka
4.96 out of 5 average rating, 108 reviews

Great for all travelers-Fenced yard-Pet friendly

Clover House is a country charmer on the edge of town. This cozy retreat provides plenty of extra room with it's spacious one bedroom. When you arrive you'll find: King bed & queen sleeper sofa Driveway parking Wi-fi & smart TV Coffee/tea/cocoa Dishwasher Washer & dryer Pet friendly Fenced backyard This is an ideal spot when traveling, vacationing or for work. You'll enjoy how private it is. For your convenience, the exact location on the map! Message me with your questions or book now!

Top guest favorite
A functional kitchen setting is depicted, featuring red cookware on a stovetop and dishes in the oven. Dark cabinetry and a stainless steel refrigerator complement the bright countertops. Natural light enters through a nearby window, and kitchen towels are displayed on a hanging rack.
Home in Elkhart
4.92 out of 5 average rating, 260 reviews

My Happy Place!!

The whole group will be comfortable in this Spacious Nicely Decor Unique space. Two bedroom and small office sitting area I’m Big on house keeping and my house rules being meet at all times Any items stolen Damaged or stained will be a $500 charge No pets , smoking ,Drugs or Guns in the unit this a Neighborhood watch community My Airbnb is setup for business workers and out of town travelers Only No Local guest Allowed Also the home is not setup for children at this time (sorry) Thank you

Top guest favorite
A blue house with a metal roof is surrounded by lush greenery. A wooden deck features two chairs and a small table, with windows allowing natural light to enter the interiors. Nearby, a gravel path leads to the house, enhancing the outdoor space.
Home in Elkhart
4.9 out of 5 average rating, 82 reviews

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.

Top guest favorite
The cabin is constructed of warm wood, surrounded by lush greenery and tall pine trees. A welcoming front porch features two chairs and flower beds, inviting relaxation. Large glass doors provide views of the outdoor space, enhancing the connection with nature.
Cabin in Goshen
4.96 out of 5 average rating, 346 reviews

Tiny home log cabin at the pines

Nurture your most important relationships at this peaceful authentic log cabin, built in 2022, set halfway in the long lane of our 18 acre property. Enjoy privacy with the massive pine trees behind you. Relax on the front porch and watch the sunset beyond the horse pasture and cornfields. The cabin boasts Wi-Fi, TV screen w options,a soaker tub, queen bed, recliners with heating feature, a full kitchen stocked with pots and pans, a washer and dryer. Everything you need for a longer stay.

Guest favorite
Home in Elkhart
4.93 out of 5 average rating, 81 reviews

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

Top guest favorite
A serene riverside view captures vibrant autumn foliage reflected in calm waters. Comfortable seating is arranged on a stone patio, overlooking the river, enhancing the tranquil outdoor experience. Sunlight dances on the water's surface, inviting relaxation and connection with nature.
Apartment in Mishawaka
4.96 out of 5 average rating, 591 reviews

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.

Superhost
Home in Osceola
5.0 out of 5 average rating, 4 reviews

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

Guest favorite
A bright living area showcases a combination of comfortable seating, including two armchairs and a sofa, arranged around a round coffee table. A dining table is positioned nearby, featuring a neutral tablecloth and a potted plant centerpiece. Light filters through sheer window curtains.
Bungalow in Elkhart
4.95 out of 5 average rating, 295 reviews

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.

Top guest favorite
The image displays a creatively designed sign reading 'Silk on the Bend,' set against a textured, warm brown brick wall. The lettering features a combination of bold and cursive styles, enhancing the welcoming identity of the space.
Guest suite in Osceola
4.95 out of 5 average rating, 637 reviews

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.

Superhost
An aerial view of the property showcases a spacious layout surrounded by lush greenery. An outdoor pool and tennis court are visible, along with a winding waterway. Nearby houses reflect a tranquil neighborhood ambiance, enhancing the property's secluded feel.
Home in Mishawaka
4.69 out of 5 average rating, 198 reviews

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!

Top guest favorite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 441 reviews

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.

Top guest favorite
Home in Elkhart
4.99 out of 5 average rating, 141 reviews

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!

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