Herbster Holiday Rentals, Wisconsin: Private House Rentals

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

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Go beyond your typical stay in Herbster

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Our top choices for Herbster hotels

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Hotel

Breakfast included

Pet-friendly

Pool

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

A bar area with a wooden counter, bar stools, a television, and a sign indicating breakfast is available for 40.

1. Cobblestone Inn & Suites - Ashland

Ashland

Dennis

฿7,321

฿8,200 total

includes taxes & fees

27 Aug - 28 Aug

2. Hotel Chequamegon, BW Signature Collection

Ashland

Michael

฿7,446

฿8,340 total

includes taxes & fees

26 Aug - 27 Aug

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

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

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

A beach with turquoise chairs and a pile of logs.

3. AmericInn by Wyndham Ashland

Ashland

Jonathan

฿8,135

฿9,111 total

includes taxes & fees

26 Aug - 27 Aug

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

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

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.

4. Quality Inn Ashland - Lake Superior

Ashland

Richard

฿7,728

฿8,655 total

includes taxes & fees

30 Aug - 31 Aug

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.

An aerial view of a marina with boats docked, a parking lot, and buildings with a large parking area.

5. The Washburn Inn - On the Lake

Washburn

Annette

฿5,881

฿6,586 total

includes taxes & fees

30 Aug - 31 Aug

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.

6. Super 8 by Wyndham Ashland

Ashland

Janice

฿6,380

฿7,146 total

includes taxes & fees

20 Sept - 21 Sept

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

A covered outdoor area with a wooden deck, potted plants, and a brick wall.

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.

7. Harbor's Edge Motel

Bayfield

Robin

฿5,018

฿5,721 total

includes taxes & fees

31 Aug - 1 Sept

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 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.

8. Blue Wave Inn

Ashland

Erik

฿5,851

฿6,554 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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.

9. Wild Rice Retreat

Bayfield

Jeffrey

฿18,200

฿20,385 total

includes taxes & fees

26 Aug - 27 Aug

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.

10. St. James Social

Bayfield

Stephen

฿11,556

฿13,174 total

includes taxes & fees

2 Sept - 3 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 beach with a sandy shore, trees, and a body of water.

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."

11. Mission Springs Resort

Ashland

Brian r

฿6,920

฿7,301 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

12. Legendary Waters Resort & Casino

Bayfield

Kera

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

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

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

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

13. Outbounder

Bayfield

Bailey

฿3,430

฿3,911 total

includes taxes & fees

2 Sept - 3 Sept

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 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.

14. Seagull Bay Motel

Bayfield

Melissa

฿7,432

฿8,473 total

includes taxes & fees

31 Aug - 1 Sept

15. The Mill House

Bayfield

Christopher

฿9,201

฿10,489 total

includes taxes & fees

1 Sept - 2 Sept

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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

Super 8 by Wyndham Ashland

10/10 Excellent

"All good"

Harbor's Edge Motel

8/10 Good

"Very accessible to everything in town"

Seagull Bay Motel

10/10 Excellent

"Beautiful location and views.of the Lake fromnthe bluff above. Short walk through trail to downtown. Rooms were small but very nice and beachy. Could not habe asked for.more!"

AmericInn by Wyndham Ashland

8/10 Good

"Great location l, nice rooms but place needs a little TLC esp in the back facing the lake. Decks needs power wash and paint, railing need paint, over grass and weeds need attention and plain garbage outside just needs to be picked up when cleaning rooms so next guest does not look at it when enjoying such beautiful lake view. We did enjoy the beach area and our dig had a blast swimming in it! (Also body wash was out in our room, please, have staff check it for next guest)."

Legendary Waters Resort & Casino

10/10 Excellent

"Clean rooms and friendly staff. No breakfast but an on-site restaurant with great food and good prices."

Quality Inn Ashland - Lake Superior

8/10 Good

"Lovely location, but lots of bugs in the room. We made a fun time of it by trying to catch them."

Hotel Chequamegon, BW Signature Collection

10/10 Excellent

"Fun Stay"

Lakeside Motel

10/10 Excellent

"It was better then I expected. Definitely worth the stop."

Second Wind Country Inn

10/10 Excellent

"What a wonderful stay. Very friendly and fun atmosphere. Would highly recommend staying here!"

More cheap stays in Herbster

Harbor's Edge Motel

33 North Front Street Bayfield WI

฿5,018

฿5,721 total

31 Aug - 1 Sept

includes taxes & fees

9.2/10 Wonderful! (961 reviews)