Madeline Island Holidays

Photo by Kate Johnson
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    Better together
    Save up to S$134 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 S$250 per night from 6 Jul to 7 Jul
S$250
6 Jul - 7 Jul
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"The location is nice. The view of Lake Superior is great. Didnt like the musty smell in the room, no ceiling fan. We tried to use the fan on air conditioning unit and had to stop as it had a really bad odor. Didnt like the rain dripping on the outdoor box outside window, kept me up overnight. Needs ..."

Reviewed on 30 Jun, 2025

The Washburn Inn - On the Lake
Super 8 by Wyndham Ashland
Super 8 by Wyndham Ashland
2 out of 5
1610 Lake Shore Dr W, Ashland, WI
The price is S$218 per night from 21 Jul to 22 Jul
S$218
21 Jul - 22 Jul
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Safe, Quite, Great location for vacationing in the Bayfield/Ashland area."

Reviewed on 30 Jun, 2025

Super 8 by Wyndham Ashland
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 S$326 per night from 7 Jul to 8 Jul
S$326
7 Jul - 8 Jul
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Receptionist was excellent"

Reviewed on 26 Jun, 2025

AmericInn by Wyndham Ashland
See all 340 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.