Madeline Island Packages (Flight + Hotel)

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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 ฿6,992 per night from 6 Aug to 7 Aug
฿6,992
฿7,831 total
6 Aug - 7 Aug
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"Staff were very nice and everything was very clean. But so creaky. We could hear every little movement the guests in the room above us made. And they weren’t loud. The hotel just squeaks and creaks so loud with every step people make you wonder if there’s someone in your room. Also there are no rooms ..."

Reviewed on 12 Jul 2026

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

Legendary Waters Resort & Casino

2.5 out of 5
37600 Onigamiing Dr Bayfield WI
The price is ฿5,230 per night from 2 Aug to 3 Aug
฿5,230
฿5,963 total
2 Aug - 3 Aug
includes taxes & fees
8/10 Very good! (479 reviews)
"Staff was so helpful and pleasant, the property sits on the lake and is an amazing view of course! The property needs updates and maintenance but I’m sure they are working on it as they can. Ate at the restaurant on a week night and rather disappointed as we went to order the fish and we were told ..."

Reviewed on 12 Jul 2026

Legendary Waters Resort & Casino
Hotel Chequamegon, BW Signature Collection

Hotel Chequamegon, BW Signature Collection

3 out of 5
101 Lake Shore Dr W Ashland WI
Fully refundableReserve now, pay when you stay
The price is ฿7,461 per night from 5 Aug to 6 Aug
฿7,461
฿8,356 total
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Balcony overlooking Lake Superior was quite nice!"

Reviewed on 12 Jul 2026

Hotel Chequamegon, BW Signature Collection
See all 374 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.

Stay near popular Madeline Island attractions

Big Bay State Park

9.2/10 (9 reviews)
Dramatic sandstone bluffs meet pristine Lake Superior beaches at this Madeline Island sanctuary. Explore seven miles of forest trails or paddle the protected lagoon for an intimate wilderness experience.
See properties

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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.