
Chequamegon Bay Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 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
Top Romantic Chequamegon Bay Hotels

Mission Springs Lake House
30190 Mission Springs Road, Ashland, WI
Book a stay at this romantic cottage, featuring a garden and jetted tubs. Couples will appreciate the in-room fireplaces, premium mattresses, and luxury ...
Couples like: spa tub, on the beach, fireplace
Wonderful!!!!!
"Looking to get away to a beautiful place with great service on one of the world’s greatest lakes? The Lake House at Mission Springs Resort near Ashland, Wisconsin on Lake Superior’s Chequamegon Bay is just that. Mission Springs Resort is a small family owned resort consisting of four cabins and The ..."
Reviewed on May 12, 2018

The Washburn Inn - On the Lake
123 Harbor View Drive, Washburn, WI
A garden and onsite dining await at this romantic hotel, which also offers a terrace and a lakeside location.
8.4/10 Very Good! (1,037 reviews)
Couples like: beachfront dining, winery tours
Travelers say...
"Lovely place, well kept… only complaint is there is no elevator… we are retired and stayed for three nights. Good thing we are in pretty good shape so we could take our luggage up the stairs."
Reviewed on Sep 27, 2025

AmericInn by Wyndham Ashland
3009 Lakeshore Drive East, Ashland, WI
A hot tub and a private beach await at this romantic hotel, which also offers a terrace and a lakeside location.
7.8/10 Good! (1,005 reviews)
Couples like: bar, hot tub, on the beach
America Matters So Let's Show That It Does
"It is a hidden gem with exceptional staff. They are doing their best to stay afloat like too many places are. The building is aged yet they do their best with what they can. The necessity of fresh linens and towels. The renovation of their breakfast area was a hidden gem with still fresh waffle toppings, ..."
Reviewed on Sep 23, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.