Madeline Island Vacation Rentals from ￥41,427: Search Short-Term Rentals

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Our top choices for Madeline Island vacation rentals

South Apartment on Main Street

Ashland

Mark

￥29,360 total

includes taxes & fees

May 20 - May 21

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Bayfield

Jenna Q.

￥41,427 total

includes taxes & fees

Jun 6 - Jun 7

Mission Springs Resort

Ashland

Kimber

￥31,728 total

includes taxes & fees

May 21 - May 22

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

Bayfield

Monica O.

￥121,787 total

includes taxes & fees

May 21 - May 22

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

Bayfield

Robyn G.

￥45,246 total

includes taxes & fees

May 19 - May 20

Annex No. 2 DePerrys | On Lake Superior Shoreline

Bayfield

Jeffrey P.

￥39,388 total

includes taxes & fees

May 19 - May 20

Bayfield Fruit Loop Retreat -2 Cottages

Bayfield

Tami N.

￥96,327 total

includes taxes & fees

May 21 - May 22

Avenue Side Room at The Copper Trout.

Bayfield

Kyle E.

￥45,805 total

includes taxes & fees

May 20 - May 21

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

Washburn

Anastasia Hopkins F.

￥96,362 total

includes taxes & fees

Jun 1 - Jun 2

Lower Flat @ Steeple Hill Flats, Bayfield

Bayfield

Tina W.

￥40,169 total

includes taxes & fees

May 19 - May 20

Annex No. 1 DePerrys | On Lake Superior Shoreline

Bayfield

Sarah S.

￥39,388 total

includes taxes & fees

May 20 - May 21

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

Bayfield

"The property is very conveniently located. Easy walk to downtown Bayfield and just 2 blocks from the Madeleine Island ferry dock. The condo is a flat which provides windows on all sides and sunlight all day long, along with a nice view of the lake directly to the east. The condo is also very nicely furnished and the kitchen is fully stocked with everything you would need to cook full meals if you wish to bring your own food. We’re already looking forward to our next trip!"

Shawn W.

￥57,005 total

includes taxes & fees

May 19 - May 20

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

Bayfield

Stacey L.

￥55,701 total

includes taxes & fees

Jun 3 - Jun 4

Bayfield Fruit Loop Retreat - Main Cottage

Bayfield

Kerry B.

￥59,477 total

includes taxes & fees

May 21 - May 22

North Apartment with Lake Superior Views

Ashland

Maura

￥41,931 total

includes taxes & fees

May 31 - Jun 1

Up North Oasis - Families & Dogs in the Bayfield Area

Washburn

Joan Q.

￥65,070 total

includes taxes & fees

Jun 8 - Jun 9

Outer Island Apartment @ The Copper Crown

Bayfield

Perry R.

￥60,540 total

includes taxes & fees

May 24 - May 25

Lake Side Room at The Copper Trout.

Bayfield

Sally R.

￥45,805 total

includes taxes & fees

May 21 - May 22

Upper Flat @ Steeple Hill Flats, Bayfield

Bayfield

￥47,873 total

includes taxes & fees

May 19 - May 20

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Top Madeline Island Hotel Reviews

AmericInn by Wyndham Ashland

10/10 Excellent

"Nice staff, clean rooms, beautiful view. They had a ton of free activities and games for kids and adults to play. This will be out go to hotel when in the area. ❤️"

Mission Springs Resort

10/10 Excellent

"We only stayed one night because we were passing through. We were upgraded from a cabin to the lake house for no charge because of a booking conflict, so that was very good for us ! Lake house was very roomy , and had lots of character. Some antique furnishings , a full kitchen and laundry, and even two tubs of locally made ice cream in the freezer ! Mainfloor washroom was way too far away away from the bedrooms for our liking , but that would be our only complaint."

Quality Inn Ashland - Lake Superior

4/10 Poor

"The older ladies at the front desk have an attitude and don’t really know if they are coming or going. When I asked to extend over the last three days I was given different answers all the way you need to talk to Tim on Monday. Oh but the way we are booked for the weekend and you’ll have to move out. lol. They can’t even properly read the computer screen for occupancy , rates or if or when things are available. Only thing that the rude ladies at the front said “we are booked for the summer”. I simply said people cancel and you won’t be booked this winter? They lost my business and the 60k in revenue they would have made from my long term stay for work."

Blue Wave Inn

8/10 Good

"The room was clean and was on the 3rd floor, and the building has an elevator. When I arrived, there was no one in the building and I had not received instructions for my arrival and had to call and leave a message. I shortly received a text and got settled. I had the Captains Room which was fine but had no true view of Lake Superior due to high, slanted windows. The lighting was too dim for me in spite of the three lamps and sink lighting. I know this is a new age of contactless entry etc., but this felt impersonal and I would have appreciated a return phone call instead of just a text. Price was O.K. and the location for furthering my travels was good for one night."

Seagull Bay Motel

10/10 Excellent

"We stayed the week for my wife's business trip to the Bayfield area. There is a lot of positive things about this place. Our unit had frontage on the main road coming into town, but it was still quiet. It is an older facility, but has been kept up or has been restored as a labor of love. It was a very clean room. The bed was quite comfortable, and the two chairs by the window were also surprisingly comfortable (I had my doubts when I first saw them.) Being up on the road at the crest of the bluff, there was a very nice view over the lake toward the island, and the unit had a decent-sized deck that would have been very nice for sitting outside if it was just a little later in the spring. One very striking feature of the unit was the retro appliances -- a small refrigerator and a microwave. The decor was simple, and I really liked the blinds. They operated very well and kept the sun out when closed. The people who own/run it were very nice and helpful. The downsides were there was no dresser or closet, no desk (just a small table), and just the bathroom sink. It was a fairly small unit and didn't have room for anything else in it. Since I was on vacation and my wife was working, I had the room to myself during the day, and it would have been nice to have a bit more room to set up my computer and work with an auxilliary kepboard, but I made do well enough. If it was warmer weather I would have been either outside more, sitting on the deck, taking a boat tour, or taking the ferry"

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Check prices for these dates

Our top choices for Madeline Island vacation rentals

South Apartment on Main Street

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Mission Springs Resort

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

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

Annex No. 2 DePerrys | On Lake Superior Shoreline

Bayfield Fruit Loop Retreat -2 Cottages

Avenue Side Room at The Copper Trout.

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

Lower Flat @ Steeple Hill Flats, Bayfield

Annex No. 1 DePerrys | On Lake Superior Shoreline

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

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

Bayfield Fruit Loop Retreat - Main Cottage

North Apartment with Lake Superior Views

Up North Oasis - Families & Dogs in the Bayfield Area

Outer Island Apartment @ The Copper Crown

Lake Side Room at The Copper Trout.

Upper Flat @ Steeple Hill Flats, Bayfield

Find vacation rentals that suit your style

Top Madeline Island Hotel Reviews

AmericInn by Wyndham Ashland

The Washburn Inn - On the Lake

Super 8 by Wyndham Ashland

Mission Springs Resort

Quality Inn Ashland - Lake Superior

Legendary Waters Resort & Casino

Hotel Chequamegon, BW Signature Collection

Blue Wave Inn

Seagull Bay Motel

Find out more about Madeline Island

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