Top Cottages in Crawford County in 2026 | Expedia

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Top cities in Crawford County

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Find holiday rentals that suit your style

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Next weekend

20 Nov - 22 Nov

In two weeks

27 Nov - 29 Nov

In one month

11 Dec - 13 Dec

In two months

Map of Crawford County

Our top choices for Crawford County cottages

A wooden deck with a round table and chairs, a barbecue grill, and a covered umbrella.

1. Serene Belgrade Hideaway With Fire Pit & Grill!

Belgrade

A wooden deck with a railing overlooking a grassy field and trees.

2. Cozy Belgrade Cottage w/ Wood-burning Stove!

Belgrade

A swimming pool with a wooden deck, surrounded by chairs and a table, with a view of a forested area.

3. Spacious Ozarks Family Home - Private Pool & Grill

Bourbon

United States

Ramon

RM2,794 total

includes taxes & fees

28 Nov - 29 Nov

A rustic wooden building labeled "WM WINERY" with a gravel driveway and large rocks in front.

4. Spacious Owensville Getaway w/ Winery On-site!

Rosebud

"I don't even know where to start with this rental. We live in the country, this farmhouse was right up our alley!! I have stayed in a lot of rental properties, this one was like being at home. I could have stayed forever. The pond served as a wonderful experience for my daughter, she loves to fish and caught many fish. My husband enjoyed watching the sunrise every morning with his cup of coffee. The restaurant was in a league of it's own, the food was spectacular. The owner was VERY responsive,...

United States

Elizabeth

A rustic cabin with a stone chimney, surrounded by tall trees and a gravel driveway.

5. Ozarks Family Retreat: River + Trail Access!

Steelville

A rustic cabin with a porch, a small deck, and a gravel ground.

6. Rustic Caledonia Cabin Near State Parks & Boating!

Caledonia

A single-story house with a front porch, a driveway, and a mailbox.

7. Charming St James Home Near Maramec Spring Park!

St. James

A white house with a porch, surrounded by trees and a gravel path.

8. Saddle Up! Belleview Farm Stay w/ Pool & Stables

Belleview

A wooden deck with white rocking chairs overlooking a grassy field and a body of water.

9. Spacious Franklin County Retreat on 80 Acres!

Luebbering

A small, single-story building with a porch, stone steps, and a door.

10. Ride, Swim & Hike! Kaolin Farms Cottage

Belleview

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