Ashland County Cottages from CA $304

A cluster of mushrooms growing on a moss-covered log in a forest.

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Top Cities in Ashland County

A coastal scene with a lighthouse, rocky breakwater, and a distant shoreline.

Our top choices for Ashland County cottages

A two-story house with a wooden deck and a staircase leading to the entrance.

1. Mission Springs Resort

Ashland

Van

CA $304 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with a railing, two white chairs, and a potted plant.

2. Brookside: Cozy Cabin Retreat, Fireplace + ATV/Snowmobile Access + Pets ok

Grand View

Haley W.

A log cabin with a wooden exterior, a front porch, and a chimney.

3. Authentic Log Cabin w/ Private Pond in Glidden

Glidden

Melanie

A wooden deck with a view of the ocean and a full moon.

4. All season cottage overlooking the private beach on Lake Superior

Washburn

Eric L.

A two-story house with a large porch, stone foundation, and a chimney.

5. Madeline Island Cottage Overlooking Apostle Islands

LaPointe

"We have stayed at this property multiple times. Our kids and grandkids all keep wanting to come back! Theresa is a wonderful host and quickly responds to any questions. We were amazed at the new induction stovetop in the kitchen and the newly refinished porch floor was great! We are already planning our trip back next summer and look forward to making more wonderful family memories at this awesome property."

Martha W.

A deck with two chairs overlooking a lake, surrounded by trees.

6. Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

Hayward

Rebecca R.

A deck with a fire feature, outdoor seating, and string lights.

7. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield

Ramalakshmi

A wooden cabin surrounded by snow-covered trees.

8. Bayfield Fruit Loop Retreat - Rock Garden Cottage

Bayfield

Robert H.

A small, single-story building with a star on the front, a bench, and a table with chairs outside.

9. SxS, UTVs and all! Access to Tuscobia Tr! Private cottage! Dogs!

Ojibwa

Megan

A wooden deck leading to a lake with clear water and a distant shoreline.

10. Corny Cottage | Escape to the Lake

Cornucopia

Andrew B.

A cabin with a porch, large windows, and a picnic table in a wooded area.

11. Beautiful Western Lakefront view on the magnificent Turtle Flambeau Flowage!

mercer

Timothy M.

A lakeside cabin with a stone deck, a covered porch, and a patio area with outdoor furniture.

12. Water's Edge Retreat on Butternut Lake!

Butternut

A snow-covered landscape with a metal railing in the foreground, a wooden shed, and a tall evergreen tree.

13. Phillips Cabin w/ Lake Views & Private Dock!

Phillips

Ray

A room with a sliding glass door leading to an outdoor deck with a view of a body of water and trees.

14. FALL DEALS! Madeline Island cottage-just steps from Lake Superior & wow views

La Pointe

Daniel N.

A campsite with two Adirondack chairs facing a fire pit surrounded by trees and a lake.

15. 15min to trailhead, King Bed, PacMan

Hayward

Anonymous traveller

CA $742 total

includes taxes & fees

Nov 12 - Nov 13

A cabin with a porch, surrounded by tall trees.

16. Superior Sanctuary: Refined Rustic in the Woods

Bayfield

Zachary

A cozy cabin interior with a dining area, a sofa, a TV, and a kitchen area with shelves and a hanging plant.

17. Little Gem Cottage in the Forest Drummond, WI

Drummond

brent M.

A two-story house with a stone chimney, a covered patio, and a view of a lake.

18. Waterfront Pike Lake Retreat: Snowmobile Paradise

Park Falls

"We have stayed in this property several times and it continues to be a winner! Home is lovely and comfortable. There is nice area to relax outside and pier available. We have a family cabin nearby, but not large enough to accommodate everyone so I rent this home and the one located on the same property (as noted in the description) for my family. It is perfect if you have a larger group.If you aren't familiar with the area, the Pike Lake Chain has great fishing and beautiful, northwoods...

Debra F.