Winona County Cottages from CA $219

A river flowing through a forest with autumn-colored trees.

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Top Cities in Winona County

A stone wall with a hole, overlooking a river and a town.

Our top choices for Winona County cottages

A small, dark blue cabin with a wooden deck and a window, surrounded by dense greenery and a small stream.

1. Stylish 1 bedroom cottage along the Mississippi River

Stoddard

Kevin

CA $219 total

includes taxes & fees

Nov 12 - Nov 13

A small blue shed with a wooden fence, surrounded by various plants and a gravel path.

2. The Alton House - Come experience tiny house living in beautiful Pepin!

Pepin

Ranell

CA $240 total

includes taxes & fees

Dec 7 - Dec 8

A wooden deck with two chairs and a table, overlooking a body of water with trees in the background.

3. Adorable Cottage on GREAT Fishing Lake

Trempealeau

Megan E.

A house with a wooden deck, a staircase, and a tree.

4. Quaint Cottage Nestled in Driftless Region: Bike, Hike, Bird & Boat

Trempealeau

Karen s

A vineyard with rows of grapevines supported by a trellis system.

5. Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

Stoddard

emily e.

A two-story house with a garage, a covered porch, and a front yard with flowers and a bench.

6. Stone's Throw Cottage - Centrally located 2-bedroom with newly remodeled kitchen

Bluffside

Arlene M.

A two-story wooden house with a deck and outdoor seating area.

7. Urban Cottage

Buffalo City

Sue B.

A single-story house with a covered porch, a grill, and a small window.

8. Studio Cottage at Lake Road Campground, on the beautiful Mississippi River.

Trempealeau

Pamela G.

A house with a green exterior, large windows, and a stone pathway leading to the entrance.

9. Quaint cottage steps from Marina

Wabasha

Michael D.

A two-story house with a porch, a small deck, and a front yard with a garden.

10. Your Home Away From Home

Coon Valley

Jack P.

A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

11. Big River Escape Parkside Bungalow

Winona

Julie

A two-story white house with a front porch, a garage, and a snow-covered driveway.

12. Steps to Root River: Home w/ Large Yard!

Preston

Ronald

A two-story yellow house with a front porch, a mailbox, and a small window.

13. Studio cottage at Lake Road Campground, on the Majestic Mississippi River.

Trempealeau

Jacqueline C.

A wooden building with a covered patio area, outdoor seating, and a barbecue grill.

14. La Crescent Cottage on Minnesota Bluffs w/ View!

La Crescent

Josh M.

A wooden deck with outdoor seating and a view of a green landscape.

15. 'fins & Flowers' Off-grid Cabin w/ Trout Fishing!

Lewiston

"We booked this cabin while in the area for a wedding. We were most looking forward to the trout stream fishing as advertised in the name. Unfortunately there was significant foliage overgrowth to the point we couldn’t access the stream due to poisonous flowers surrounding all the trails. We were unaware of the flowers until reading about it in a welcome book on the property. There was also a significant carpenter ant infestation in the bathroom and loft sleeping area. The beds had a significant...

Jenna