Madeline Island Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Madeline Island Vacation Packages

Madeline Island Hotel Deals

The Washburn Inn - On the Lake

The Washburn Inn - On the Lake

2.5 out of 5
123 Harbor View Drive, Washburn, WI
Fully refundableReserve now, pay when you stay
The price is ₩179,865 per night from Sep 1 to Sep 2
₩179,865
₩201,449 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"We liked the location of the property. Right next to the water and a nice walking path. The air conditioner in the room was way too loud! It kept cycling on and off every few minutes even after I raised the temp on it. We ended up opening the window and turning it off. I noticed the light that indicated ..."

Reviewed on Aug 24, 2025

The Washburn Inn - On the Lake
Legendary Waters Resort & Casino

Legendary Waters Resort & Casino

2.5 out of 5
37600 Onigamiing Dr, Bayfield, WI
Fully refundableReserve now, pay when you stay
The price is ₩247,799 per night from Aug 26 to Aug 27
₩247,799
₩282,491 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (338 reviews)
"I've stayed here 2 times and have only been happy with my stay. The location is fabulous with sweeping views of Lake Superior all around. I feel that it is an excellent value for what you get compared to other hotels and inns on the water. The staff has always been friendly and I find the size of ..."

Reviewed on Aug 24, 2025

Legendary Waters Resort & Casino
AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

2.5 out of 5
3009 Lakeshore Drive East, Ashland, WI
Fully refundableReserve now, pay when you stay
The price is ₩303,004 per night from Aug 26 to Aug 27
₩303,004
₩339,365 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Our bathroom ceiling had a slow water drip above the toilet. We called maintenance and they fixed it quickly."

Reviewed on Aug 15, 2025

AmericInn by Wyndham Ashland
See all 341 properties in Madeline Island
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.

Frequently asked questions

How much does a Madeline Island vacation package cost?
Get your credit card ready, because a trip to Madeline Island starts from an enticing . When you combine your flights, hotels and car rentals into a vacation package, you'll land the biggest bargains.
How do I get a cheap travel package to Madeline Island?
Combine your bookings with Expedia to save big bucks on your next getaway. With more than 550 airlines and 1,000,000 properties around the globe, your Madeline Island vacation package can be tailored exactly to suit your travel style. With all that extra cash, why not throw in some exciting activities and tours? It's an easy way to unlock even more bargains. Your dream vacation in Madeline Island is much closer than you thought!
How far in advance should I book my Madeline Island vacation?
To score cheap prices, book as early as you can. Airlines usually begin selling tickets, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to Madeline Island, there are always plenty of great deals to be had on Expedia. Book your escape today!
What does an Expedia Madeline Island travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply choose your preferred bundle and get access to great discounts. Once you've made your booking, add on some tours and experiences and watch your savings stack up. When it comes to crafting your Madeline Island escape, you're the one in control!
What should I know before booking a Madeline Island travel package?
When you book your hotels, flights and car rentals together, you'll pick up great discounts. Whether you're planning an island getaway in a villa or would rather stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Madeline Island Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Simply pick the carrier you want and put together your ideal Madeline Island trip.
If I'm not able to travel, can I cancel my Madeline Island vacation package?
Because we know life is full of surprises, the answer is yes. For further information, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.