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Search Holiday Rentals in Madeline Island

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Top Holiday Rentals in Madeline Island

On the beach
# 1 Lakeside
10.0 out of 10, Exceptional, (119)
"Property was in great shape,great communication with the property owner. Will rent there again."
The price is £348
includes taxes & fees
22 May - 23 May
# 1 Lakeside
Exterior
Weisel Cabin - Nostalgic Cabin located within walking distance of Downtown La
10.0 out of 10, Exceptional, (9)
"We (my dog and I) thoroughly enjoyed our days at Weidel Cottage. Took walks in the evening to take pictures of the sunset, found the Madeline Museum quite interesting, and enjoyed our morning coffee taking in the view of Lake Superior,"
Weisel Cabin - Nostalgic Cabin located within walking distance of Downtown La
Exterior
Charming Vintage 1950's Cottage
10.0 out of 10, Exceptional, (7)
"The cottage was the perfect accommodation for my husband and I while our daughter attended the Madeline Island School of the Arts for the week. The lake views are stunning and you can hear the waves gently hitting the shore…so relaxing. We spent 2 days exploring Big Bay State Park which is only a few miles away. The cottage was well equipped. We had everything we needed including paper towels, soap, toilet paper, hair dryer and more. Thank you Frank!"
Charming Vintage 1950's Cottage
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On the beach, sun-loungers
Motisi's Sandy Beach
10.0 out of 10, Exceptional, (56)
"We went with friends to the Applefest in Bayfield. We enjoyed taking the car ferry to Madeline Island to our rental property. We found the accommodations to be enjoyable with sitting on the porch for coffee, playing games by the fire place, walking the beach, roasting marshmallows at the fire pit. the host was very accessible! everyone we encounter on the island was friendly and loved their unique island. hiking was gorgeous in the parks. Definitely recommend!"
Motisi's Sandy Beach
Fridge, microwave, oven, stovetop
Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed - 1 block from marina
10.0 out of 10, Exceptional, (11)
"We loved our stay! The full kitchen was perfect for our 6 person group. Our stay was hidden in the trees, but was perfectly located near downtown Bayfield. The view at our Marina was beautiful and the area was full of adventure including a bakery, multiple orchards, & fish markets! 10/10 would recommend staying here."
Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed - 1 block from marina
Exterior
Hike-in, Off-Grid Camping: an A-frame Cabin
10.0 out of 10, Exceptional, (13)
"Amazing views, very clean and had everything we needed"
The price is £154
includes taxes & fees
23 May - 24 May
Hike-in, Off-Grid Camping: an A-frame Cabin
Property grounds
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
10.0 out of 10, Exceptional, (82)
"Home was well stocked, especially the kitchen. Liked the open floor plan very much. Secluded property low vehicle usage on the road. Definitely on our radar if we are in the area. Our two yorkies had a good time as well."
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
Property grounds
Bell Street Lodging-Suite
9.8 out of 10, Exceptional, (78)
"Great Bed and Shower."
Bell Street Lodging-Suite
Interior
Spirit Lodge- Log Cabin with Large front porch
9.8 out of 10, Exceptional, (38)
"Owner was friendly and helpful."
Spirit Lodge- Log Cabin with Large front porch
On the beach, sun-loungers
OPENINGS THIS SUMMER!!Madeline Island cottage within steps of Lake Superior
9.8 out of 10, Exceptional, (63)
"4th time there loved it as always"
OPENINGS THIS SUMMER!!Madeline Island cottage within steps of Lake Superior
Exterior
SUMMER SPECIALS Beautiful lake front, beach and pool table
9.8 out of 10, Exceptional, (13)
"We loved everything about our stay - such a great experience. The house was beautiful and checked all of our boxes plus more. Bonus being able to sit on the deck and see the lake. I can’t wait to bring my family back."
SUMMER SPECIALS Beautiful lake front, beach and pool table
Beach
Top coastal town/Apostle Is.'s gateway/next to scenic marinas/fireplace/jacuzzi
9.8 out of 10, Exceptional, (152)
"Great place to stay and I'd like to visit again but not in April. All of the Bayfield shops are closed for the season in April."
The price is £135
includes taxes & fees
24 May - 25 May
Top coastal town/Apostle Is.'s gateway/next to scenic marinas/fireplace/jacuzzi
Exterior
The Little Bodin
9.8 out of 10, Exceptional, (9)
"Excellent clean apartment in an upstairs unit in Bayfield. Clean and comfortable."
The price is £236
includes taxes & fees
21 May - 22 May
The Little Bodin
Terrace/patio
The Carriage House Sleeps 4. Downtown Bayfield! Walk to everything!
9.8 out of 10, Exceptional, (31)
"We came to Bayfield purposefully after the AppleFest to avoid some of the crushing crowds. We appreciated the text that notified us of an early check-in opportunity but we had some stops on the road, so didn’t get there in time to take advantage of that. The communication emails prior to the trip were very concise and nicely organized. The property is well represented in the VRBO listing. There were no surprises, and we were quite pleased wiith everything. We wanted a place that was fairly...
The Carriage House Sleeps 4. Downtown Bayfield! Walk to everything!
Property grounds
#2 Island Overlook, #2 Island Overlook
9.8 out of 10, Exceptional, (7)
"Beautiful scenery, close to many good places to eat and explore. Cabin was exactly as advertised, extremely clean and comfortable."
#2 Island Overlook, #2 Island Overlook
Beach
Bayfield condo in downtown Bayfield, Wisconsin. Patio, Lake Views! Sleeps 4.
9.8 out of 10, Exceptional, (197)
"Cannot stress enough how great the Andrew Tate Condos are to stay in when visiting Bayfield. Great quality for the price and right in the heart of downtown Bayfield so within walking distance of everything! This was our first time in the city and are definitely going to go back and stay at these condos. 5 Star rating!"
The price is £277
includes taxes & fees
9 Jun - 10 Jun
Bayfield condo in downtown Bayfield, Wisconsin. Patio, Lake Views! Sleeps 4.
Property grounds
Privacy in the Valhalla Hills near Bayfield/ Lake Superior. On ATV/Snow trails.
9.8 out of 10, Exceptional, (90)
"What a beautiful place inside and out! Definitely one of the best we've stayed at! The drive in was a little rough because of the frozen dirt road, but it was worth it for the large private property where our dog loved roaming freely!"
Privacy in the Valhalla Hills near Bayfield/ Lake Superior. On ATV/Snow trails.
Property grounds
3 Bears Guest Cottage at South Shore Vista Overlooking Lake Superior
9.6 out of 10, Exceptional, (4)
"A cozy space to get away from everything. Only a 10 minute bike ride from town and the ferry back to Bayfield, this hideaway is an ideal home base to see the area."
3 Bears Guest Cottage at South Shore Vista Overlooking Lake Superior
Dining
Sunset Bay Lodge.
9.6 out of 10, Exceptional, (46)
"It was a great escape for extended family on the island. We enjoyed the lake, fires and plenty of family time together."
Sunset Bay Lodge.
Property grounds
Escape To Madeline Island ! Superior Lakefront 2 Bedroom Condo
9.6 out of 10, Exceptional, (69)
"We truly loved our stay at this cozy condo. Everything about it was perfect. Clean, conveniently located, spacious, comfortable with beautiful views. You can tell the owners put a lot of thought into the furnishings to make it a really nice getaway spot."
Escape To Madeline Island ! Superior Lakefront 2 Bedroom Condo
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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.

Other types of properties in Madeline Island you may be interested in

On the beach, sun-loungers
OPENINGS THIS SUMMER!!Madeline Island cottage within steps of Lake Superior
9.8 out of 10, Exceptional, (63)
"4th time there loved it as always"
OPENINGS THIS SUMMER!!Madeline Island cottage within steps of Lake Superior
Exterior
<br>Beautiful home on Madeline Island for summer specials
9.6 out of 10, Exceptional, (66)
"We had a lovely time enjoying the island. Our two families were comfortable in this charming home. We played with the kids in the beautiful spacious yard and enjoyed making dinners together in the well stocked kitchen."
<br>Beautiful home on Madeline Island for summer specials
Dining
Sunset Bay Lodge.
9.6 out of 10, Exceptional, (46)
"It was a great escape for extended family on the island. We enjoyed the lake, fires and plenty of family time together."
Sunset Bay Lodge.
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.

Everything you need to know about Madeline Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madeline Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madeline Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Madeline Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madeline Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madeline Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madeline Island holiday rentals we have selected for you start as low as £135 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madeline Island rentals

At Expedia, we put the best Madeline Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Madeline Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madeline Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madeline Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews of Madeline Island properties
Expedia verified reviews

Legendary Waters Resort & Casino

Legendary Waters Resort & Casino

5/5 Excellent
"Wonderful location, nice casino, beautiful view of Lake Superior. Kind and knowledgeable staff. Definitely coming again!"
A verified traveller stayed at Legendary Waters Resort & Casino
Posted 3 days ago
Legendary Waters Resort & Casino