Herbster Holiday Rentals, Wisconsin: Private House Rentals

A harbor with boats, a lighthouse, and houses on a hillside.

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Our top choices for Herbster hotels

A marina filled with various boats at sunset.

A grassy outdoor area with white chairs arranged in rows, a small arbor, and a bench.

An aerial view of a hotel with a parking lot, a marina with boats, and a body of water in the background.

A row of colorful Adirondack chairs and tables by a lakeside, with a clear view of the water and distant shoreline.

1. The Washburn Inn - On the Lake

Washburn

Michael

Rp1.463.570

Rp1.639.199 total

includes taxes & fees

19 Oct - 20 Oct

A modern bedroom with a large bed, two bedside tables with lamps, a ceiling fan, and a window with curtains.

A compact kitchenette with a coffee maker, microwave, and a small refrigerator.

A compact kitchenette with a microwave, coffee maker, sink, and dishwasher.

A motel with a simple, single-story structure, a parking lot, and a signboard.

2. Lakeside Motel

Ashland

Patti

Rp1.342.725

Rp1.504.031 total

includes taxes & fees

12 Oct - 13 Oct

A modern bedroom with a wooden bed, a TV mounted on the wall, and a seating area with a sofa and chairs.

A wooden staircase with white railings leading to a lofted area. A bench with cushions is placed against the wall below the staircase.

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

A row of white cabins with wooden railings and a grassy lawn.

3. Seagull Bay Motel

Bayfield

Melissa

Rp2.779.441

Rp3.168.652 total

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a stone wall, a fireplace, leather sofas, and glass coffee tables.

A Cobblestone Inn & Suites building with a brick facade, a covered entrance, and a parking lot.

A modern restaurant with a bar area, seating, and a large window offering a view of the street.

A hotel room with a large bed, a sofa, a desk, and a framed picture on the wall.

4. Cobblestone Inn & Suites - Ashland

Ashland

jolene

Rp2.561.919

Rp2.869.349 total

includes taxes & fees

20 Oct - 21 Oct

A multi-level indoor pool area with stone walls and wooden railings.

A two-story log cabin with a stone foundation, a green roof, and a balcony overlooking a lake.

A wooden deck with a table and chairs overlooking a calm body of water.

A modern kitchen with dark wood cabinets, a large stove, and a microwave.

5. Quality Inn Ashland - Lake Superior

Ashland

Tammy

Rp3.028.292

Rp3.391.687 total

includes taxes & fees

26 Oct - 27 Oct

An outdoor patio with a table and chairs, overlooking a body of water at sunset.

A hotel room with two beds, a TV, a desk, and a chair.

A dining area with multiple tables and chairs, large windows offering a view of the sea, and a carpeted floor.

A beach with turquoise chairs and a pile of logs.

6. AmericInn by Wyndham Ashland

Ashland

Jonathan

Rp2.846.577

Rp3.188.345 total

includes taxes & fees

19 Oct - 20 Oct

A modern building with a unique architectural design, situated on a rocky shoreline with a body of water in the foreground.

A modern building with large windows and outdoor seating.

A restaurant with a large round window overlooking the sea, wooden tables and chairs, and a staircase leading to an upper level.

A wooden staircase leading to a bright room with large windows and a view of a parking lot.

7. Blue Wave Inn

Ashland

Dawn

Rp2.400.792

Rp2.688.886 total

includes taxes & fees

22 Oct - 23 Oct

A large white building with a green roof, a covered entrance, and a view of the water.

A bar area with a long counter, multiple taps, and bar stools.

A grand lobby with a central staircase, wooden columns, and a chandelier.

A restaurant with wooden tables and chairs, a kitchen area, and a clock on the wall.

8. Hotel Chequamegon, BW Signature Collection

Ashland

DOROTHY

Rp3.204.816

Rp3.589.395 total

includes taxes & fees

18 Oct - 19 Oct

A framed photograph of a turbulent sea on a wall, a bedside lamp, and a pillow on a bed.

A pool area with wooden walls, a pool, and several chairs.

A living room with a sofa, a coffee table, a TV, and a cabinet.

A motel with a brick facade, a covered entrance, and a row of chairs outside.

9. Super 8 by Wyndham Ashland

Ashland

Ann

Rp2.327.390

Rp2.606.676 total

includes taxes & fees

26 Oct - 27 Oct

A room with two patterned armchairs, a small table with a lamp, and a mirror on the wall.

A spacious living room with a wooden staircase, a green sofa, and a lamp on a side table.

A bedroom with a large bed, two bedside lamps, a chair, and a window with curtains.

A living room with a green sofa, a brown leather armchair, a wooden coffee table, and a window with a view of trees.

10. Pinehurst Inn - Luxury Bayfield Hotel

Bayfield

Carrie

Rp3.684.616

Rp4.126.770 total

includes taxes & fees

25 Oct - 26 Oct

A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

A dining area with a white table, chairs, and a chandelier. There is a sign on the wall that reads "Welcome to THE LAKE HOUSE."

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

A modern kitchen with white cabinetry, stainless steel appliances, and a patterned rug.

11. Mission Springs Resort

Ashland

Brian r

Rp2.646.833

Rp2.792.408 total

includes taxes & fees

27 Oct - 28 Oct

A rooftop terrace with wicker furniture, a view of the sea, and a brick building in the background.

A modern bedroom with a large bed, a wooden chair, a small table, and a hanging light fixture.

A bar area with a leather couch, wicker chairs, and a bar counter.

A dining area with a wooden ceiling, wicker furniture, and a central floral arrangement.

12. St. James Social

Bayfield

Michelle

Rp6.345.503

Rp7.233.875 total

includes taxes & fees

21 Oct - 22 Oct

A balcony with wicker furniture, a small table, and a view of a marina with boats and cars.

A bathroom with a white door, a sink with a mirror, and a framed picture on the wall.

A compact kitchen with a sink, microwave, and coffee maker. There is a wooden chair and a small table.

A room with a sofa, two rocking chairs, a bed with a headboard, a TV, and a lamp.

13. Harbor's Edge Motel

Bayfield

Grace

Rp2.154.805

Rp2.456.471 total

includes taxes & fees

5 Oct - 6 Oct

A bar with a view of a lake and boats, large windows, and hanging light fixtures.

A view from a room with a door leading to a deck overlooking a body of water and a forested area.

Outdoor wicker lounge chairs and a table in front of a building with red and blue exterior walls and multiple windows.

A spacious lobby with a stone fireplace, comfortable seating, and a patterned floor.

14. Legendary Waters Resort & Casino

Bayfield

Michael

A room with a wooden deck visible through a glass door, a wooden table, and two black chairs.

A living room with a sofa, wooden flooring, a chandelier, and a large window with a view.

A room with a wooden floor, a round table with chairs, a potted plant, and a bed with a white headboard.

A cozy room with wicker furniture, a small table with a lamp, and a view through large windows.

15. Outbounder

Bayfield

Helen

Rp2.953.995

Rp3.367.733 total

includes taxes & fees

29 Sept - 30 Sept

A cozy loft-style room with a dining area, a kitchen, and a staircase.

A brown leather sofa with a striped pillow and a tall, textured floor lamp.

A bedroom with a bed, a nightstand, a wooden ceiling, a kitchenette, and a window with curtains.

A room with a bed, a sofa, a small table, a chair, a TV, and a window with curtains.

16. The Mill House

Bayfield

Christopher

Rp4.363.856

Rp4.974.886 total

includes taxes & fees

20 Oct - 21 Oct

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Stay near popular Herbster attractions

Bark Bay Slough State Natural Area

This pristine 646-acre wetland sanctuary along Lake Superior shelters rare plants and diverse birdlife. Paddle through the coastal lagoon and explore the pine-forested barrier spit for an intimate wilderness experience.

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Flag River State Wildlife Area

This pristine wildlife area showcases diverse ecosystems where Lake Superior meets boreal forests and wetlands. Observe steelhead runs while exploring trails rich with migratory birds.

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Learn more about Herbster

Nestled along Lake Superior's pristine shoreline, this quiet hamlet invites visitors to explore the rugged beauty of Apostle Islands Mainland Sea Caves. Kayak through the crystal waters of Bark Bay Slough State Natural Area or hike Flag River's wildlife trails for an authentic northwoods experience.

See all hotels in Herbster

A rocky shoreline with clear water and lush greenery.

Top Herbster Hotel Reviews

Harbor's Edge Motel

10/10 Excellent

"Great Place right across from the Madeline Island ferry. Within walking distance to restaurants and shops."

Lakeside Motel

10/10 Excellent

"This place was adorable. It had everything you needed in your room. The towels were wonderful. They felt very high-end. I loved that there was a little area with a refrigerator and a little coffee bar. There was even a little table if you wanted to eat in your room. The only thing that I guess I would have to say was negative about my experience here was the bed was really hard. It was a little uncomfortable, but other than that this place was adorable.."

The Washburn Inn - On the Lake

10/10 Excellent

"Great location, clean rooms"

St. James Social

10/10 Excellent

"The check-in was odd. Thought there would be a desk. Also restaurant wasn’t open when we were there. Nice rooftop, lovely room. Very clean. They did provide beverages and occasional snacks. Not sure if this was supposed to be everyday. One day was lovely charcuterie and some breakfast things."

Hotel Chequamegon, BW Signature Collection

10/10 Excellent

"Very nice hotel, staff was very helpful and the sunset view was amazing."

Super 8 by Wyndham Ashland

10/10 Excellent

"It was ok"

Outbounder

10/10 Excellent

"Room was clean, nice and quiet, within walking distance to nearby amenities"

Seagull Bay Motel

10/10 Excellent

"The room was just about perfect for what we were looking for. Nice kitchenette, bed was comfortable, air conditioning worked well and this was a very nice location for the walk on the path into town. Only 10 minutes and we were in the midst of the restaurants and also the boat tour and ferry to Madeline Island."

More cheap stays in Herbster