Madeline Island Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
123 Harbor View Drive Washburn WI
Fully refundableReserve now, pay when you stay
₩129,790
₩145,365 total
Oct 19 - Oct 20
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Enjoyed our stay! Staff was wonderful, room was clean, spacious shower with chair for accessibility. No complaints :)"
Reviewed on Oct 4, 2026
Cobblestone Inn & Suites - Ashland
818 Main Street W. Ashland WI
Fully refundableReserve now, pay when you stay
₩191,969
₩215,006 total
Oct 21 - Oct 22
includes taxes & fees
9.4/10 Exceptional! (840 reviews)
"We've stayed here several times, but this time I made the reservation. We've noticed some things sliding. More and more often, no one is at the desk upon arrival or at check out. Had to wait for someone to show up to check in. Not sure if they are short staffed or if the staff has more responsibilities ..."
Reviewed on Oct 6, 2026
Harbor's Edge Motel
33 North Front Street Bayfield WI
₩269,105
₩306,774 total
Oct 10 - Oct 11
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Great location."
Reviewed on Oct 2, 2026
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.
Madeline Island Museum
9.0/10 (17 reviews)
Housed in the 1835 American Fur Company Building, this museum chronicles Madeline Island's Native American and fur trade history. Explore maritime artifacts while staff illuminate the island's cultural significance.
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.
