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

Madeline Island Holiday Rentals

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Our top choices for Madeline Island holiday rentals

1. Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint

Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint
Bayfield
10.0 out of 10, Exceptional, (2 reviews)
"The condo was very clean and everything you would need was there. Lisa was very responsive to any questions we had, and was very helpful. We would definitely recommend it to others."
United States
Carol
The price is HK$733
HK$1,419 total
includes taxes & fees
3 Nov - 4 Nov
Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint

2. PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
Bayfield
10.0 out of 10, Exceptional, (1 review)
"Great location, nice view from bedroom. Easy in and out and good communication. Could use darker shades."
United States
scott d.
The price is HK$863
HK$1,819 total
includes taxes & fees
3 Nov - 4 Nov
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

3. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (67 reviews)
"Very clean and cozy cabin near Bayfield and Meyers beach"
United States
Reed C.
The price is HK$1,863
HK$3,247 total
includes taxes & fees
3 Nov - 4 Nov
Woodland Chalet @ Brickyard Creek, Bayfield

4. Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (83 reviews)
"Beautiful place!"
United States
Susan S.
The price is HK$2,010
HK$3,430 total
includes taxes & fees
3 Nov - 4 Nov
Northwoods Chalet @ Brickyard Creek, Bayfield

5. The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Bayfield
10.0 out of 10, Exceptional, (44 reviews)
"Enjoyed our few nights at this lovely home. So many special touches! Really enjoyed the screened in area and lighting fires and having smores around the fire pit."
United States
elizabeth
The price is HK$1,451
HK$2,011 total
includes taxes & fees
16 Nov - 17 Nov
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

6. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (26 reviews)
"Nice and cozy with a great view. The outside spaces could use some tidying up and paint, but once inside the place was awesome."
United States
Lori
The price is HK$1,177
HK$1,848 total
includes taxes & fees
3 Nov - 4 Nov
Lower Flat @ Steeple Hill Flats, Bayfield

7. Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Bayfield
10.0 out of 10, Exceptional, (23 reviews)
"Location and the host are incredible!"
United States
Michelle N.
The price is HK$1,373
HK$2,915 total
includes taxes & fees
3 Nov - 4 Nov
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

8. Downtown Bayfield Lodging in Historic Building

Downtown Bayfield Lodging in Historic Building
Bayfield
9.2 out of 10, Wonderful, (5 reviews)
"Loved the rooms! Enjoyed the views of the lake and the quaint downtown area. It was a very quiet and enjoyable stay. I gave it 4 stars only because the sofa was so hard and uncomfortable. We stayed in 2 nights to watch the Brewers play (YAY!) but it was very difficult to get comfortable on the sofa and no amount of throw pillows could change that. That being said, the bed was a dream and the kitchen well appointed. Would I stay there again? Maybe if the sofa was swapped out."
United States
Susan
The price is HK$2,010
HK$3,491 total
includes taxes & fees
3 Nov - 4 Nov
Downtown Bayfield Lodging in Historic Building

9. Lake Shore Home with private dock and large deck--1 mile from Bayfield

Lake Shore Home with private dock and large deck--1 mile from Bayfield
Bayfield
10.0 out of 10, Exceptional, (124 reviews)
"Great property! wonderful rejuvenation time for myself and my family"
United States
Brian
The price is HK$2,353
HK$4,534 total
includes taxes & fees
4 Nov - 5 Nov
Lake Shore Home with private dock and large deck--1 mile from Bayfield

10. Brookside Hide-A-Way #2, Port Superior, Bayfield

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (42 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is HK$1,373
HK$2,162 total
includes taxes & fees
3 Nov - 4 Nov
Brookside Hide-A-Way #2, Port Superior, Bayfield

11. Main @ Hendrickson House

Main @ Hendrickson House
Bayfield
10.0 out of 10, Exceptional, (3 reviews)
"Very nice and spotless. Also a great location within a couple blocks of almost everything. We’ll be back."
United States
Aaron G.
The price is HK$2,206
HK$4,222 total
includes taxes & fees
3 Nov - 4 Nov
Main @ Hendrickson House

12. Carriage House - Chequamegon Bay, Bayfield

Carriage House - Chequamegon Bay, Bayfield
Bayfield
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Nice and clean."
United States
Janet H.
The price is HK$1,951
HK$3,834 total
includes taxes & fees
3 Nov - 4 Nov
Carriage House - Chequamegon Bay, Bayfield

13. Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course
Bayfield
9.8 out of 10, Exceptional, (22 reviews)
"Awesome place! Views of the golf course was amazing!"
United States
Anonymous traveller
The price is HK$1,951
HK$3,834 total
includes taxes & fees
3 Nov - 4 Nov
Apostle Pines #4 @ Apostle Highlands Golf Course

14. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (25 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is HK$777
HK$1,390 total
includes taxes & fees
9 Nov - 10 Nov
South Apartment on Main Street

15. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (82 reviews)
"Clean room, great locations"
United States
Van
The price is HK$1,601
HK$1,689 total
includes taxes & fees
16 Nov - 17 Nov
Mission Springs Resort

16. Upper Flat @ Steeple Hill Flats, Bayfield

Upper Flat @ Steeple Hill Flats, Bayfield
Bayfield
8.6 out of 10, Excellent, (18 reviews)
"Great views of Superior and comfortable stay"
United States
Josh F.
The price is HK$1,324
HK$2,144 total
includes taxes & fees
15 Nov - 16 Nov
Upper Flat @ Steeple Hill Flats, Bayfield

17. North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (46 reviews)
"Great location, clean and comfortable. "
United States
Heather Ann M.
The price is HK$981
HK$1,718 total
includes taxes & fees
8 Nov - 9 Nov
North Apartment with Lake Superior Views

18. Carriage @ Hendrickson House

Carriage @ Hendrickson House
Bayfield
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful vacation. This little house was perfect for two people. It had all the amenities that were needed. The best part was it was walking distance to absolutely everything. Prime location. Will definitely be back and staying here again."
United States
Wendy D.
The price is HK$2,010
HK$3,491 total
includes taxes & fees
15 Nov - 16 Nov
Carriage @ Hendrickson House

19. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
8.8 out of 10, Excellent, (44 reviews)
"We had a great time! Beautiful home with easy access to all the South Shore has to offer. "
United States
Anastasia Hopkins F.
The price is HK$1,640
HK$3,427 total
includes taxes & fees
3 Nov - 4 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

20. Up North Oasis - Families & Dogs in the Bayfield Area

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
9.8 out of 10, Exceptional, (14 reviews)
"Nice house, and nice location."
United States
ben H.
The price is HK$1,138
HK$2,574 total
includes taxes & fees
29 Nov - 30 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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