Madeline Island Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Kate Johnson

  • Plan, book, travel with confidence

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    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Madeline Island

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 ฿4,223 per night from 1 Sept to 2 Sept
฿4,223
฿4,730 total
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"Our room was ready and we were able to check in early. We appreciated that."

Reviewed on 23 Aug 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
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 24 Aug 2025

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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 ฿7,110 per night from 24 Sept to 25 Sept
฿7,110
฿7,964 total
24 Sept - 25 Sept
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 15 Aug 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 holiday 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 holiday 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 holiday 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 holiday in Madeline Island is much closer than you thought!
How far in advance should I book my Madeline Island holiday?
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 holiday 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 holiday 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.