
Holiday houses in Osceola
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Osceola
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

Couples, Lake Michigan Close, Hot Tub, Private,
Imagine soaking in a private hot tub under a star filled sky, while a gentle creek flows just steps away. Surrounded by trees and pure country quiet. This secluded couples' retreat in Southwest Michigan is your escape from everything. Enjoy a meal, book, or game while watching our feathered friends at the bird feeder right outside your door. Leave the noise behind and reconnect in a quiet setting. Lake Michigan, Amish Country Shipshewana, and Wine Country are all within 45 minutes of us.

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.

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.

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

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.

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!

Russ Street Retreat - 10 minutes from Notre Dame
This southwest style oasis is 10 minutes from Notre Dame or short walk to Bethel University. Three bedrooms, an open living area, and a bright kitchen makes it an easy choice for your next getaway. A large, private yard and ample parking also makes this location a great stay for game day. It is within walking distance to many shops and restaurants. Pet dishes and treats available upon request.

Gameday Hideaway, 15 min to ND
Welcome to our little slice of Midwestern charm in Osceola, Indiana! This cozy cottage is perfect for couples or solo travelers looking for a warm, inviting stay. Enjoy a cheerful bedroom, comfy living room, fully stocked kitchen, and washer/dryer. Surrounded by greenery yet just 15 minutes from Notre Dame, it’s the ideal spot for game days, exploring South Bend, or a peaceful getaway.

The Guesthouse on 29 Near Shipshewana, Notre Dame
Relax and unwind at The Guesthouse on 29, conveniently located just 1.5 miles off of US Highway 20. This cozy retreat is ideal for travelers exploring Northern Indiana and Amish Country. Enjoy easy access to nearby attractions — 10 minutes to Goshen and Middlebury, 15 minutes to Elkhart, 20 minutes to Shipshewana, and only 40 minutes to the University of Notre Dame.
Popular amenities for Osceola holiday rentals
Other great holiday rentals in Osceola

Cozy "DOG friendly" cottage

Gorgeous 2BR home near ND (absolutely no parties)

Choo Choo Inn

Chelsea Upstairs Studio for One Person

Cozy Stay in Quiet Area, 3 BDR & Fenced Yard

"Cozy Arts & Crafts period retreat" comfy!

Close to Notre Dame

Treehouse Acres
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- Cleveland Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Lexington Holiday rentals
- Traverse City Holiday rentals
- London Holiday rentals
- Downtown Chicago Holiday rentals
- Warren Dunes State Park
- Indiana Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Silver Beach Carousel
- Beachwalk Vacation Rentals
- Potato Creek State Park
- New Buffalo Public Beach
- 12 Corners Vineyards
- Van Buren State Park
- Grand Mere State Park
- Shady Creek Winery
- Woodlands Course at Whittaker
- Weko Beach
- Jean Klock Park
- Four Winds Casino
- Silver Beach Park
- Blue Gate Restaurant & Bakery
- Four Winds Casino
- Dablon Winery and Vineyards
- Studebaker National Museum
- Potawatomi Zoo
- Four Winds Field
- Howard Park





