Madeline Island Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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 NT$6,760 per night from Jul 26 to Jul 27
NT$6,760
NT$7,571 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Clean, quiet, perfect! We were only here overnight, quite place to land, right on the water for a summer night-beautiful! The restaurant that shares the parking lot was DELICIOUS! Harbor Table. So glad I picked this place!"

Reviewed on 2026/7/8

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 NT$5,765 per night from Aug 2 to Aug 3
NT$5,765
NT$6,573 total
Aug 2 - Aug 3
includes taxes & fees
8/10 Very Good! (476 reviews)
"Nice would stay again"

Reviewed on 2026/7/10

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 NT$7,693 per night from Jul 12 to Jul 13
NT$7,693
NT$8,617 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Breakfast was good for a free one and overall was very pleased with the staff and facilities. Bathrooms could use an update though."

Reviewed on 2026/7/10

Hotel Chequamegon, BW Signature Collection
See all 372 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 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.

Explore a world of travel with Expedia

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