Book Holiday Homes in Chequamegon Bay

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chequamegon Bay

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

Ashland
A stay at this vacation home places you in the heart of Ashland, within a 10-minute walk of Lake Superior and Ashland Mural Walk.
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Private Beach and Endless Water

Private Beach and Endless Water

La Pointe
With a stay at this vacation home in La Pointe, you'll be on a lake, within a 10-minute drive of Lake Superior and Big Bay State Park.
Private Beach and Endless Water
Michigan Suite @ The Bayfield Guest House

Michigan Suite @ The Bayfield Guest House

Bayfield
The price is AU$409 per night from 19 Aug to 20 Aug
AU$409
19 Aug - 20 Aug
includes taxes & fees
A stay at this vacation home places you in the heart of Bayfield, within a 10-minute walk of Lake Superior and Bayfield Heritage Museum.
Michigan Suite @ The Bayfield Guest House
Save an average of 15% on thousands of hotels when you're signed in
Sunshine  House | Historic Bayfield Farmhouse

Sunshine House | Historic Bayfield Farmhouse

Bayfield
When you stay at this vacation home in Bayfield, you'll be on a lake, within a 5-minute walk of Lake Superior and Bayfield Heritage Museum.
Sunshine House | Historic Bayfield Farmhouse
Beachfront and  Lakehouse With All of the Comforts!

Beachfront and Lakehouse With All of the Comforts!

Herbster
With a stay at this vacation home in Herbster, you'll be on the beach, within a 10-minute drive of Lake Superior and Bark Bay Slough State Natural Area.
Beachfront and Lakehouse With All of the Comforts!
Private & Spacious Lake Superior Lakefront Cabin on Bark Point

Private & Spacious Lake Superior Lakefront Cabin on Bark Point

Herbster
When you stay at this vacation home in Herbster, you'll be on the beach, just steps from Lake Superior and a 3-minute drive from Bark Bay Slough State Natural ...
Private & Spacious Lake Superior Lakefront Cabin on Bark Point
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

Washburn
When you stay at this vacation home in Washburn, you'll be on a lake, within a 10-minute walk of Lake Superior and StageNorth.
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Huron Suite @ The Bayfield Guest House, Bayfield

Huron Suite @ The Bayfield Guest House, Bayfield

Bayfield
The price is AU$328 per night from 11 Sept to 12 Sept
AU$328
11 Sept - 12 Sept
includes taxes & fees
A stay at this vacation home places you in the heart of Bayfield, within a 10-minute walk of Lake Superior and Bayfield Heritage Museum.
Huron Suite @ The Bayfield Guest House, Bayfield
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

Bayfield
With a stay at this vacation home, you'll be centrally located in Bayfield, within a 5-minute walk of Lake Superior and Christ Episcopal Church.
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Don't see what you're looking for?
See all available properties in Chequamegon Bay
View all properties
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.

Chequamegon Bay Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chequamegon Bay vacation homes are the perfect way for you to wing it.

Holiday houses in Chequamegon Bay let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chequamegon Bay in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chequamegon Bay adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chequamegon Bay with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chequamegon Bay vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chequamegon Bay Holiday Homes essential information

Accommodation
114 Holiday Homes
Lowest Price
AU$223
Highest Price
AU$409
Popular accommodation
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior, Private Beach and Endless Water , Michigan Suite @ The Bayfield Guest House, Sunshine House | Historic Bayfield Farmhouse, Beachfront and Lakehouse With All of the Comforts!, Private & Spacious Lake Superior Lakefront Cabin on Bark Point, Spacious four bedroom house -walking distance to Lake Superior / Washburn shops, Huron Suite @ The Bayfield Guest House, Bayfield, Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

Top trending hotels in Chequamegon Bay

The Washburn Inn - On the Lake

The Washburn Inn - On the Lake

2.5 out of 5
123 Harbor View Drive, Washburn, WI
The price is AU$223 per night from 4 Sept to 5 Sept
AU$223
4 Sept - 5 Sept
includes taxes & fees
When you stay at The Washburn Inn - On the Lake in Washburn, you'll be connected to the convention center, just steps from Lake Superior and 4 minutes by foot ...
The Washburn Inn - On the Lake
AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

2.5 out of 5
3009 Lakeshore Drive East, Ashland, WI
The price is AU$376 per night from 4 Sept to 5 Sept
AU$376
4 Sept - 5 Sept
includes taxes & fees
When you stay at AmericInn by Wyndham Ashland in Ashland, you'll be next to a golf course, just steps from Lake Superior and a 2-minute drive from Bayview ...
AmericInn by Wyndham Ashland
Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

2.5 out of 5
818 Main Street W., Ashland, WI
A stay at Cobblestone Inn & Suites - Ashland places you in the heart of Ashland, steps from Lake Superior and Ashland Mural Walk.
Cobblestone Inn & Suites - Ashland
Save an average of 15% on thousands of hotels when you're signed in
Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

2 out of 5
1610 Lake Shore Dr W, Ashland, WI
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 8 Sept to 9 Sept
AU$250
8 Sept - 9 Sept
includes taxes & fees
With a stay at Super 8 by Wyndham Ashland in Ashland, you'll be within a 5-minute drive of Ashland Mural Walk and Ashland Historical Museum.
Super 8 by Wyndham Ashland
Don't see what you're looking for?
See all available properties in Chequamegon Bay
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.