Ashland Holiday Rentals, Wisconsin: Private House Rentals

A sandy beach with a wooden structure extending into the water.

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Our top choices for Ashland hotels

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

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

1. Hotel Chequamegon, BW Signature Collection

Ashland

3.316.184 ₫

3.714.126 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

2. Cobblestone Inn & Suites - Ashland

Ashland

Joshua

3.702.283 ₫

4.146.764 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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.

3. Super 8 by Wyndham Ashland

Ashland

Bonni

3.127.399 ₫

3.502.635 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

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

4. Quality Inn Ashland - Lake Superior

Ashland

3.366.492 ₫

3.770.471 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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 microwave, coffee maker, sink, and dishwasher.

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

A living room with a black leather sofa, a wooden chair, a small table with two stools, a floor lamp, and a large mirror.

5. Lakeside Motel

Ashland

Cheryl

1.940.400 ₫

2.173.507 ₫ total

includes taxes & fees

18 Oct - 19 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 modern building with large windows and outdoor seating.

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

6. Blue Wave Inn

Ashland

Dawn

2.305.195 ₫

2.582.025 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

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

A beach with turquoise chairs and a pile of logs.

7. AmericInn by Wyndham Ashland

Ashland

Jonathan

3.236.587 ₫

3.625.184 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

8. Mission Springs Resort

Ashland

Brian r

4.511.857 ₫

4.760.010 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A marina filled with various boats at sunset.

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

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.

9. The Washburn Inn - On the Lake

Washburn

3.596.208 ₫

4.028.012 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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.

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

10. Pinehurst Inn - Luxury Bayfield Hotel

Bayfield

Carrie

3.985.489 ₫

4.463.748 ₫ total

includes taxes & fees

2 Nov - 3 Nov

An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and tables.

A multi-story hotel with a brick facade, a covered entrance, and a flagpole.

A hotel room with a kitchenette, a dining area with wooden chairs and a table, a refrigerator, a microwave, and a television.

11. Days Inn by Wyndham Hurley

Hurley

Brittany

3.496.601 ₫

3.863.744 ₫ total

includes taxes & fees

20 Oct - 21 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 modern bedroom with a large bed, a wooden chair, a small table, and a hanging light fixture.

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

12. St. James Social

Bayfield

Michelle

8.570.241 ₫

9.770.074 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

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

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.

13. Seagull Bay Motel

Bayfield

Dave

4.551.066 ₫

5.188.475 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A restaurant with a bar area, wooden tables, and chairs. There is a large wooden wall with skis displayed on it.

A bar area with a wooden counter, multiple bar stools, and a television mounted on the wall.

A window with a view of a snowy landscape and a wooden shelf with various wine bottles.

A group of off-road vehicles parked on a grassy slope with trees in the background.

14. Whitecap Mountains Resort

Upson

Stephanie

3.824.528 ₫

4.822.896 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A spacious living room with a large Christmas tree, multiple windows, and a high ceiling with exposed beams.

A spacious room with a piano, multiple seating areas, large windows, and a mountain view.

A bedroom with a bed, a dresser, a chair, a window with curtains, and a framed certificate on the wall.

A cozy living room with a fireplace, a television, a chessboard, and a large window offering a view of the outdoors.

15. Davos Chalet

Upson

Ruslan

4.411.137 ₫

4.653.750 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A motel with a sign indicating air conditioning, vacancy, and color TV.

A Coach USA RV parked in a snowy area with a building in the background.

A man standing behind a reception desk with a painting, framed certificates, and a clock on the wall.

A compact kitchen with wooden cabinets, a refrigerator, a coffee maker, and a small table.

16. Cedars Motel

Ironwood

gughan

3.363.360 ₫

3.766.964 ₫ total

includes taxes & fees

14 Oct - 15 Oct

17. Econo Lodge Hurley - Ironwood

Hurley

Jennifer

2.683.703 ₫

3.046.002 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A room with a bed, a desk, a chair, a lamp, and a framed picture on the wall.

A reception desk with a laptop, a 'WELCOME' sign, a wall calendar, and a lamp.

A kitchenette with a microwave, refrigerator, and a flat-screen TV mounted on a wooden wall.

A bathroom with a toilet, sink, and shower curtain.

18. Royal Motel

Ironwood

Jennifer

2.561.328 ₫

2.868.687 ₫ total

includes taxes & fees

25 Oct - 26 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.

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

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

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

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.

20. Outbounder

Bayfield

Helen

4.278.780 ₫

4.878.069 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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Stay near popular Ashland attractions

Northern Great Lakes Visitor Center

9.2/10 (120 reviews)

Immerse yourself in Lake Superior's rich heritage through interactive exhibits and a five-story observation tower. Explore the interpretive boardwalk through wetland habitats.

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Chequamegon Bay Golf Course

8.2/10 (23 reviews)

Enjoy panoramic views of Lake Superior on this championship course with rolling terrain and four tee sets. Morning rounds offer the best conditions, avoiding afternoon winds off the bay.

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Ashland Mural Walk

9.2/10 (54 reviews)

Stroll through Ashland's historic city centre to discover over 20 vibrant murals depicting the city's rich past. Grab a self-guided tour book from the Historical Museum to uncover stories behind each artistic masterpiece.

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Soo Line Locomotive 950

This historic 1900 Baldwin steam locomotive once hauled ore across the region's railways. View the massive engine under its protective pavilion while exploring the restored Soo Line Depot nearby.

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Ashland Historical Museum

8.6/10 (42 reviews)

Step into the past at this free museum showcasing Ashland's timber, shipping, and railway heritage. Explore exhibits and archives while learning about the Edmund Fitzgerald shipwreck from knowledgeable volunteers.

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Ore Dock Park

Walk along the remnants of Ashland's historic iron ore shipping industry on Lake Superior's picturesque shoreline. The park offers peaceful waterfront views where industrial heritage meets natural beauty.

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Learn more about Ashland

Nestled on Lake Superior's southern shore, this charming town boasts a vibrant arts scene and outdoor adventures. Catch a show at the historic Ashland Theatre, then explore the Apostle Islands' sea caves by kayak in nearby Bayfield.

See all hotels in Ashland

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

Top Ashland Hotel Reviews

The Washburn Inn - On the Lake

10/10 Excellent

"The location was great - right on the lake, but also close to the other businesses on the Main Street. It's a very basic hotel, but it was very clean and comfortable. The staff was very friendly and they did have freshly-brewed coffee in the lobby, made from beans ground daily. They also had in-room coffee, but it was worth the trip to the lobby. We had a partial lake view from the 2nd floor, so that was an added bonus."

Royal Motel

8/10 Good

"Room was clean. We like the idea of parking in front of our room"

Super 8 by Wyndham Ashland

10/10 Excellent

"Everything was really great."

Seagull Bay Motel

10/10 Excellent

"Beautiful location within easy 5-10 minute walking distance to downtown Bayfield shops, restaurants, and the ferry to Madeline Island. We were there for peak fall leaves color. The view of the lake, the island, the small marina, the trees, and the sunrise from the cozy furniture on the deck outside our door was amazing. It is a motel, so there is the potential for noise from the vehicles that park outside the rooms, but it was a non-issue. Our stay was peaceful, pleasant, and perfect."

Whitecap Mountains Resort

10/10 Excellent

"All staff were super accommodating and very friendly. The restaurant on site has really good food. We stayed 4 nights and ate there 3 times."

Quality Inn Ashland - Lake Superior

10/10 Excellent

"Great place and a great view from our room."

Mission Springs Resort

10/10 Excellent

"Very modern and beautiful, while nestled in trees. We will stay again when in the area."

Harbor's Edge Motel

10/10 Excellent

"Great Inn right on the waterfront."

Days Inn by Wyndham Hurley

8/10 Good

"clean room"

More cheap stays in Ashland

Super 8 by Wyndham Ashland

1610 Lake Shore Dr W Ashland WI

3.127.399 ₫

3.502.635 ₫ total

12 Nov - 13 Nov

includes taxes & fees

8/10 Very good! (1,003 reviews)

Quality Inn Ashland - Lake Superior

30600 Us Highway 2 Ashland WI

3.366.492 ₫

3.770.471 ₫ total

10 Nov - 11 Nov

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

Days Inn by Wyndham Hurley

13355 N. US Hwy 51 Hurley WI

3.496.601 ₫

3.863.744 ₫ total

20 Oct - 21 Oct

includes taxes & fees

8.4/10 Very good! (982 reviews)

The Washburn Inn - On the Lake

123 Harbor View Drive Washburn WI

3.596.208 ₫

4.028.012 ₫ total

19 Oct - 20 Oct

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

Cobblestone Inn & Suites - Ashland

818 Main Street W. Ashland WI

3.702.283 ₫

4.146.764 ₫ total

22 Oct - 23 Oct

includes taxes & fees

Harbor's Edge Motel

33 North Front Street Bayfield WI

Get rates

9.2/10 Wonderful! (1,007 reviews)

Hotels in Ashland with star rating

Frequently asked questions

What's the weather like in Ashland?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -7°C. The snowiest months in Ashland are April, March, January and December, with each month seeing an average of 50 cm of snowfall.

Explore a world of travel with Expedia

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Book Hotels in Ashland on Expedia.com

Find hotels in Ashland, WI from 2.173.507 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Ashland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Ashland hotels

1. Hotel Chequamegon, BW Signature Collection

2. Cobblestone Inn & Suites - Ashland

3. Super 8 by Wyndham Ashland

4. Quality Inn Ashland - Lake Superior

5. Lakeside Motel

6. Blue Wave Inn

7. AmericInn by Wyndham Ashland

8. Mission Springs Resort

9. The Washburn Inn - On the Lake

10. Pinehurst Inn - Luxury Bayfield Hotel

11. Days Inn by Wyndham Hurley

12. St. James Social

13. Seagull Bay Motel

14. Whitecap Mountains Resort

15. Davos Chalet

16. Cedars Motel

17. Econo Lodge Hurley - Ironwood

18. Royal Motel

19. Legendary Waters Resort & Casino

20. Outbounder

Stay near popular Ashland attractions

Northern Great Lakes Visitor Center

Chequamegon Bay Golf Course

Ashland Mural Walk

Soo Line Locomotive 950

Ashland Historical Museum

Ore Dock Park

Learn more about Ashland

Top Ashland Hotel Reviews

The Washburn Inn - On the Lake

Royal Motel

Super 8 by Wyndham Ashland

Seagull Bay Motel

Whitecap Mountains Resort

Quality Inn Ashland - Lake Superior

Mission Springs Resort

Harbor's Edge Motel

Days Inn by Wyndham Hurley

More cheap stays in Ashland

Super 8 by Wyndham Ashland

Quality Inn Ashland - Lake Superior

Days Inn by Wyndham Hurley

The Washburn Inn - On the Lake

Cobblestone Inn & Suites - Ashland

Harbor's Edge Motel

Hotels in Ashland with star rating

Frequently asked questions

Explore a world of travel with Expedia

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