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Holiday Homes in Madeline Island

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Madeline Island and around

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Terrace/patio

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

10.0 out of 10, Exceptional, (36)
"This place was very nice, it had everything we needed for a long weekend. "
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Private Beach and Endless Water
Beach nearby, sun-loungers, beach towels

Private Beach and Endless Water

8.8 out of 10, Excellent, (42)
"Very little traffic and very quiet beach. It was early in the year before tourist season but very quiet neighborhood. Would definitely stay here again. House was very clean. "
Private Beach and Endless Water
Michigan Suite @ The Bayfield Guest House
Exterior

Michigan Suite @ The Bayfield Guest House

9.4 out of 10, Exceptional, (22)
"Clean good bed "
The price is €233
includes taxes & fees
19 Aug - 20 Aug
Michigan Suite @ The Bayfield Guest House
Sunshine House | Historic Bayfield Farmhouse
Property grounds

Sunshine House | Historic Bayfield Farmhouse

9.8 out of 10, Exceptional, (13)
"Great place to stay while visiting Bayfield!"
Sunshine House | Historic Bayfield Farmhouse
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Exterior

Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

9.4 out of 10, Exceptional, (26)
"This home was wonderful! My family of 6 had more than enough room here and everyone had their own space. There was plenty of towels for us to use. The beds were comfy, we all slept great. We ate dinner one night at Patsy's. Definitely recommend eating there, it was delicious, and we could walk there from the house! The grocery store is also within walking distance. The location was perfect! We spent half our time in Ashland, the other half in Bayfield! Washburn is about halfway between the two....
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Huron Suite @ The Bayfield Guest House, Bayfield
Exterior

Huron Suite @ The Bayfield Guest House, Bayfield

9.4 out of 10, Exceptional, (18)
"We enjoyed soo many great things on our 1st visit to Bayfield! The Guest House was a perfect location to everything"
The price is €187
includes taxes & fees
11 Sept - 12 Sept
Huron Suite @ The Bayfield Guest House, Bayfield
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Terrace/patio

Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

10.0 out of 10, Exceptional, (3)
"This house is a great place to stay. We highly recommend!"
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Erie Suite @ The Bayfield Guest House, Bayfield
1 bedroom, desk, free WiFi, bed sheets

Erie Suite @ The Bayfield Guest House, Bayfield

9.0 out of 10, Wonderful, (14)
" Very nice property, the management was great about making sure we were comfortable and taken care of. And what a view!"
The price is €190
includes taxes & fees
1 Sept - 2 Sept
Erie Suite @ The Bayfield Guest House, Bayfield
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse

8.8 out of 10, Excellent, (5)
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Property grounds

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!

10.0 out of 10, Exceptional, (20)
"As far as a place to disconnect there is not better place! "
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Balsam House in Washburn, Wisconsin
Sun-loungers, beach towels

Balsam House in Washburn, Wisconsin

2.0 star property
9.6 out of 10, Exceptional, (14)
"Nice home in quiet location. Beds were super comfy, well stocked kitchen. Close to all the dining options in town. "
Balsam House in Washburn, Wisconsin
Spacious home with EV charging station two miles from Big Bay Town Park.
Property grounds

Spacious home with EV charging station two miles from Big Bay Town Park.

10.0 out of 10, Exceptional, (3)
"We had a great experience. It was a quick driving distance to the big bay town park which makes it very convenient for beach access. Beautiful home with plenty of room for my children to hang out and play. The hosts are very thoughtful and quick to respond. Strongly recommend and will love to come back again. "
Spacious home with EV charging station two miles from Big Bay Town Park.
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Fridge, microwave, oven, stovetop

Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

10.0 out of 10, Exceptional, (52)
"Had a great weekend stay, the house was very clean and well kept. The owners have done an excellent job fixing it up. The owners do a great job with communication as well. I'd highly recommend staying here. "
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Luxurious Lake Superior Estate with Outdoor Hot Tub
Exterior

Luxurious Lake Superior Estate with Outdoor Hot Tub

10.0 out of 10, Exceptional, (54)
"Loved the property close to everything house was great. I would recommend this place anytime. "
Luxurious Lake Superior Estate with Outdoor Hot Tub
4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!
Marina

4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!

9.8 out of 10, Exceptional, (76)
"We enjoyed the large space with all the bedrooms. Very close to Big Bay Town Park. "
4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Interior

Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

10.0 out of 10, Exceptional, (47)
"Loved the location and the convenience of check in. My girls loved the candy machine!"
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Motisi's Sandy Beach
On the beach, sun-loungers, beach towels

Motisi's Sandy Beach

10.0 out of 10, Exceptional, (69)
"We enjoyed our stay and loved the beautiful location and view of the water. It's a very spacious and can accommodate a family. "
Motisi's Sandy Beach
Ontario Suite @ The Bayfield Guest House
Exterior

Ontario Suite @ The Bayfield Guest House

9.0 out of 10, Wonderful, (26)
"Loved the location and property. Everything within walking distance, which is exactly what we wanted. Would definitely stay here again."
The price is €243
includes taxes & fees
26 Aug - 27 Aug
Ontario Suite @ The Bayfield Guest House
Superior Suite @ The Bayfield Guest House
1 bedroom, desk, free WiFi, bed sheets

Superior Suite @ The Bayfield Guest House

9.8 out of 10, Exceptional, (19)
"Great location, easy walk into town. "
The price is €263
includes taxes & fees
11 Sept - 12 Sept
Superior Suite @ The Bayfield Guest House
Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland
Fridge, microwave, oven, stovetop

Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland

9.6 out of 10, Exceptional, (7)
"Our family greatly enjoyed several nights at this cozy cottage! It was clean, had lots of lovely amenities, and was close to Ashland, Washburn and Bayfield. When we had a question, Chelsie responded quickly and thoroughly. Would absolutely recommend it for couples and small families. It didn’t quite provide the lake view we hoped for, but perhaps as leaves fall off, there will be a better view!"
Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland
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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Top Madeline Island Hotel Reviews

Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

10/10 Excellent
"This property is downtown, but in a quiet area. The room was very nice, clean, and they have some nice breakfast options available that are included with your stay. Some fun and unique food and shopping experiences are also available in Ashland. "
Lee 1-night trip
Posted 1 day ago
Cobblestone Inn & Suites - Ashland