Madeline Island Holiday Rentals, Wisconsin: Private House Rentals

A rocky shoreline with clear water, a small tree on a rock formation, and lush greenery.

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Go beyond your typical stay in Madeline Island

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Our top choices for Madeline Island hotels

1. Hotel Chequamegon, BW Signature Collection

Ashland

Todd

6.494.181 ₫

7.273.712 ₫ total

includes taxes & fees

13 Sept - 14 Sept

Superior Double Room, Private Bathroom, Lake View (Guest House) | Floor plan

Cottage, Private Bathroom, Lake View | Lobby

Superior Double Room, Private Bathroom, Lake View (Guest House) | Lounge

Double Room, Private Bathroom, Lake View (King/Lake View (Room 2)) | Exterior

2. Seagull Bay Motel

Bayfield

Melissa

5.881.040 ₫

6.704.646 ₫ total

includes taxes & fees

14 Sept - 15 Sept

Desk, blackout curtains, iron/ironing board, bed sheets

3. AmericInn by Wyndham Ashland

Ashland

Jonathan

6.493.920 ₫

7.273.451 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Premium bedding, pillow-top beds, in-room safe, desk

4. Cobblestone Inn & Suites - Ashland

Ashland

jolene

4.870.440 ₫

5.454.892 ₫ total

includes taxes & fees

13 Sept - 14 Sept

Suite, 1 King Bed, Non Smoking, Lake View (Upper Floor) | Desk, iron/ironing board, free WiFi, alarm clocks

5. Quality Inn Ashland - Lake Superior

Ashland

Richard

6.169.224 ₫

6.909.530 ₫ total

includes taxes & fees

13 Sept - 14 Sept

6. The Washburn Inn - On the Lake

Washburn

Annette

2.738.400 ₫

3.067.269 ₫ total

includes taxes & fees

4 Oct - 5 Oct

Design Suite, 1 King Bed, Accessible, Non Smoking (Sailor's Retreat #2) | 1 bedroom, premium bedding, down duvets, pillow-top beds

7. Blue Wave Inn

Ashland

Dawn

4.670.928 ₫

5.231.648 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Standard Room, 1 Queen Bed | Desk, laptop workspace, iron/ironing board (on request), rollaway beds

Studio Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, iron/ironing board (on request), rollaway beds

8. Super 8 by Wyndham Ashland

Ashland

Janice

5.111.680 ₫

5.725.082 ₫ total

includes taxes & fees

8 Oct - 9 Oct

Standard Suite, 1 King Bed | Free WiFi, bed sheets

Standard Suite, 1 King Bed | Private kitchen | Coffee/tea maker, fridge, microwave, paper towels

9. Lakeside Motel

Ashland

Jason

2.477.600 ₫

2.775.173 ₫ total

includes taxes & fees

9 Sept - 10 Sept

King ADA | Laptop workspace, soundproofing, free WiFi, bed sheets

10. St. James Social

Bayfield

Stephen

12.585.217 ₫

14.347.147 ₫ total

includes taxes & fees

17 Sept - 18 Sept

Coffee/tea maker, fridge, microwave, oven

11. Mission Springs Resort

Ashland

Brian r

4.540.189 ₫

4.789.900 ₫ total

includes taxes & fees

4 Oct - 5 Oct

Double Room, Ensuite, Lake View (Private Deck, Non-ADA) | View from property

Economy Double Room, Ensuite (1st Floor, Non-ADA)

Superior Suite, Ensuite (Rm 13A, Floor 2, Non-ADA) | Private kitchen | Ice maker

12. Harbor's Edge Motel

Bayfield

Robin

2.223.320 ₫

2.534.715 ₫ total

includes taxes & fees

5 Oct - 6 Oct

TreeHaus Room | Desk, free WiFi, bed sheets

13. Wild Rice Retreat

Bayfield

Jeffrey

16.172.208 ₫

18.112.874 ₫ total

includes taxes & fees

13 Sept - 14 Sept

14. Legendary Waters Resort & Casino

Bayfield

Hon Wah

Comfort Double Room, Ensuite, Lake View (Kitchenette ) | Interior

Family Cottage, Private Bathroom, Lake View (Brownstone Cottage) | Interior

Comfort Triple Room, Private Bathroom, Lake View (Residence) | Interior

15. Outbounder

Bayfield

Landon

3.520.800 ₫

4.013.973 ₫ total

includes taxes & fees

15 Sept - 16 Sept

Panoramic Suite, Ensuite, City View (The Mill House #4) | Shared kitchen

Panoramic Suite, Ensuite, Lake View (The Mill House #1)

Panoramic Suite, Ensuite, Lake View (The Mill House #1) | Interior

Panoramic Suite, Ensuite, City View (The Mill House #4) | Lounge

16. The Mill House

Bayfield

Christopher

5.053.000 ₫

5.760.550 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Madeline Island attractions

Big Bay State Park

9.2/10 (9 reviews)

Dramatic sandstone bluffs meet pristine Lake Superior beaches at this Madeline Island sanctuary. Explore seven miles of forest trails or paddle the protected lagoon for an intimate wilderness experience.

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Madeline Island Museum

9.0/10 (17 reviews)

Housed in the 1835 American Fur Company Building, this museum chronicles Madeline Island's Native American and fur trade history. Explore maritime artefacts while staff illuminate the island's cultural significance.

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Learn more about Madeline Island

Head to sights like Madeline Island Museum and Big Bay State Park as you discover Madeline Island—a family-friendly area also known for its island views.

See all hotels in Madeline Island

A rocky shoreline with clear water and lush greenery.

Top Madeline Island Hotel Reviews

Harbor's Edge Motel

10/10 Excellent

"Location was excellent for visiting Apostle Island National Park and catching the ferry to Madeline Island. Easy walking distance to good restaurants and tourist shops. Very quiet neighborhood"

Super 8 by Wyndham Ashland

8/10 Good

"Excellent breakfast for a smaller hotel. Room ok but a little musty smelling"

Cobblestone Inn & Suites - Ashland

10/10 Excellent

"Just need better warmer for the hot breakfast foods!"

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."

AmericInn by Wyndham Ashland

10/10 Excellent

"We loved staying here, it was just for 2 nights and I didn’t want to leave. The private beach was a HUGE bonus and it was so peaceful."

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."

Seagull Bay Motel

10/10 Excellent

"Very clean room and close to downtown Bayfield. We didn’t spend much time there due to all the area things to explore. We would stay at this property again!"