Herbster Holiday Rentals, Wisconsin: Private House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Herbster

Pet friendly

Apartment

Condo

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Herbster hotels

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

A beach with turquoise chairs and a pile of logs.

An indoor swimming pool with a wooden ceiling, slides, and poolside chairs.

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

1. AmericInn by Wyndham Ashland

Ashland

Jonathan

6.484.209 ₫

7.262.574 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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

A traditional living room with leather furniture, a fireplace, and a bookshelf.

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

2. Hotel Chequamegon, BW Signature Collection

Ashland

Todd

6.484.469 ₫

7.262.834 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

A modern living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall.

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

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

3. Seagull Bay Motel

Bayfield

Melissa

5.881.040 ₫

6.704.646 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

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

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

A room with a round table, chairs, a flat-screen TV, and large windows offering a view of a body of water and trees.

4. Quality Inn Ashland - Lake Superior

Ashland

Richard

6.159.999 ₫

6.899.199 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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 marina with boats docked, a parking lot, and buildings with a large parking area.

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

5. The Washburn Inn - On the Lake

Washburn

Annette

2.734.305 ₫

3.062.682 ₫ total

includes taxes & fees

6 Oct - 7 Oct

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

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

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.

6. Cobblestone Inn & Suites - Ashland

Ashland

jolene

4.863.157 ₫

5.446.736 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

A hotel room with a large bed, a chair, a lamp, and a view of the water through the windows.

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

4.670.928 ₫

5.231.648 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

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

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

8. Super 8 by Wyndham Ashland

Ashland

Janice

5.104.036 ₫

5.716.520 ₫ total

includes taxes & fees

8 Oct - 9 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 motel with a simple, single-story structure, a parking lot, and a signboard.

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

9. Lakeside Motel

Ashland

Jason

2.477.600 ₫

2.775.173 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

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.

A beach with a sandy shore, trees, and a body of water.

10. Mission Springs Resort

Ashland

Brian r

4.540.189 ₫

4.789.900 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

11. St. James Social

Bayfield

Stephen

11.835.756 ₫

13.492.763 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A modern two-story house with large windows, a flat roof, and a well-lit exterior.

A cozy bedroom with a bed, a small table, and a chair. There are large windows offering a view of trees.

A cozy room with wooden walls, a skylight, a small table with chairs, and a kitchenette.

A modern log cabin interior with a dining area, a bed, and a large window offering a forest view.

12. Wild Rice Retreat

Bayfield

Jeffrey

16.172.208 ₫

18.112.874 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

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.

13. Harbor's Edge Motel

Bayfield

Robin

2.223.320 ₫

2.534.715 ₫ 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 waterfront hotel with multiple buildings, a dock, and a speedboat on the water.

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

Dale

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

A modern kitchen with a white countertop, black bar stools, a wooden ceiling, and a window with a towel rack.

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

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

15. Outbounder

Bayfield

Landon

3.520.800 ₫

4.013.973 ₫ total

includes taxes & fees

15 Sept - 16 Sept

A compact kitchen with wooden cabinets, a stainless steel stove, a refrigerator, and a small island with bar stools.

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

A bedroom with a bed, bedside lamps, a window with curtains, and a door.

A two-story house with a balcony, surrounded by a garden with various plants and flowers.

16. The Mill House

Bayfield

Christopher

6.357.000 ₫

7.247.110 ₫ total

includes taxes & fees

16 Sept - 17 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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 location, right close to pier, within walking distance to shops, ferry and apostle island cruise. Convenient parking, very nice property, clean with very nice rooms. Easy check inn, quiet location. Enjoyed stay very much!"

AmericInn by Wyndham Ashland

8/10 Good

"Clean room, games were old, had tubes to float on the lake, good beach, pools were ok, great staff"

The Washburn Inn - On the Lake

8/10 Good

"Staff was great. Property is dated but clean. Great location by the marina with beaches nearby. Very quiet."

Super 8 by Wyndham Ashland

8/10 Good

"Nice breakfast. Clean room. Helpful staff. All good."

Legendary Waters Resort & Casino

8/10 Good

"Nice being on the water can sit outside. Casino connected was fun"

St. James Social

10/10 Excellent

"This was a wonderful place to stay. The rooms are bright, comfortable beds and a beautiful bathroom. The room had a record player with a couple of old records in it. We found that pretty fun. It has a nice bar and restaurant downstairs that we enjoyed a great meal, a little pricey. . The staff were fun, kind and helpful. The breakfast was a typical European style breakfast which I and my friend enjoyed coffee was great. The only thing I would like to see is more hanging space in the bathroom.and a second chair in the room."

Lakeside Motel

8/10 Good

"Very nice motel to stay at. Clean room, friendly staff and very close to everything in town."

Great Water Inn

8/10 Good

"Room was well laid out and clean, great location."

Outbounder

10/10 Excellent

"Great distance from Bayfield and the walking trail into town was very convenient."