Top Cottages in Osceola County in 2026

An aerial view of a coastal city with high-rise buildings, a curved waterfront promenade, and a beach.

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Our top choices for Osceola County cottages

A wooden deck with a white picket fence overlooking a calm lake.

1. Lakefront Group Getaway w/ Dock in Baldwin!

Baldwin

"Excellent property! We stayed for graduation weekend for our son’s graduation from Ferris State. Only a quick 30 minute drive to campus, this property was a quiet and relaxing place to celebrate with family and friends. There were plenty of bedrooms for everyone to have their own space, enough bathrooms that no one waited in line and a spacious kitchen for preparing and serving food. We enjoyed the fire pit and grill, as well as the two sitting rooms and the big dining room table and game room...

Linda

A two-story cabin with a red front door and windows, surrounded by trees and a grassy area with a fire pit and chairs.

2. Peaceful Lake Escape: Near Dining & Winter Trails

Lake

Nicole

A white house with a porch, a bench, and a small garden area.

3. Golf Getaway in Cadillac: Deck + Putting Green

Cadillac

Theresa

A two-story house with a covered porch, a garage, and a small yard with trees.

4. Hunt, Snowmobile, Fish: Accessible Baldwin Home

Baldwin

5. Northern Michigan Summer Retreat on Crooked Lake!

Lake

A wooden deck with a railing overlooking a campsite surrounded by trees.

6. Little Manistee Riverfront Cabin w/ Fire Pit!

Irons

A riverside view with a house adjacent to the water.

7. Rustic River View Cabin w/ Fire Pit, Games & Grill

Falmouth

A multi-story building with a balcony and a covered porch area.

8. Rustic Crooked Lake Cottage w/ Views & Deck

Lake

Lisa

A cabin surrounded by a forest with snow on the ground.

9. Remote Michigan Retreat on 10 Acres w/ Grill!

Wellston

A wooden deck with outdoor seating, a barbecue grill, and a view of a forested area.

10. Wooded Country Home w/ Spacious Deck in Farwell!

Farwell

Heather

A residential driveway leading to a garage with a light-colored house and a dark garage door.

11. Sand Lakefront Retreat Private Dock & Fire Pit

Harrison

A wooden deck with a table and chairs, overlooking a forested area with a stream.

12. Custom Log Cabin w/ Deck & 45 Acres By Pine River!

Tustin

A blue single-story house with a covered patio area, a small outdoor seating arrangement, and a visible front door.

13. Fish & Hike: Riverfront Cabin in Paris

Paris

Ronald

A wooden deck with Adirondack chairs and a fire pit, overlooking a frozen lake with houses in the background.

14. Pet Friendly Home on Lake w/ Dock, Firepit & More!

Farwell

Anonymous traveller

A modern kitchen with white cabinets, stainless steel appliances, and a wooden island.

15. Pet-friendly Harrison Home: 1 Mi to Wilson St Park

Harrison

A wooden deck with a glass table and chairs, a red umbrella, and a view of the surrounding greenery.

16. Pet-friendly Stanwood Sanctuary w/ Fire Pit!

Stanwood

A lakeside property with a dock, a boat, and a grassy area with a wooden deck and a bench.

17. Diamond Lake Waterfront Cabin w/ Deck + Dock!

Tustin

A single-story house with a porch, a garage, and a snow-covered yard.

18. Waterfront Evart House on Chippewa Lake Channel

Evart

"The cottage was perfect for our trip. The bunk bed with a trundle was great for the teens while the adults were comfortable in the other two bedrooms (we didn’t have need for the Murphy bed in the living room, but if we had a larger group, it was another sizable bed! The bed linens and towels were all new and the appliances, too. I always appreciate a place with a washer and dryer, and they provided detergent. The hosts also had extras like snacks and drinks from Michigan in a basket for us and...

Gina