Book Holiday Homes in Chequamegon Bay

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Featured Holiday Homes in Chequamegon Bay

300' of Private Beach

300' of Private Beach

La Pointe
Located in La Pointe, this vacation home is on the waterfront, a 1-minute drive from Lake Superior and 5 minutes from Big Bay State Park.
300' of Private Beach
Motisi's Sandy Beach

Motisi's Sandy Beach

La Pointe
With a stay at this vacation home in La Pointe, you'll be on the beach, just steps from Lake Superior and a 5-minute drive from Big Bay State Park.
Motisi's Sandy Beach
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

Washburn
Located in Washburn, this vacation home is in a rural location, within a 15-minute walk of Bayfield County Courthouse and StageNorth.
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
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Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

Bayfield
With a stay at this vacation home in Bayfield, you'll be within a 5-minute drive of Apostle Highlands Golf Course and Lake Superior.
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
3+ Bedroom House +SAUNA,  Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Washburn
The price is AU$666 per night from 25 Nov to 26 Nov
AU$666
includes taxes & fees
25 Nov - 26 Nov
With a stay at this vacation home in Washburn, you'll be within a 5-minute drive of Lake Superior and Bayfield County Courthouse.
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
SUMMER SPECIALS  Beautiful lake front, beach and pool table

SUMMER SPECIALS Beautiful lake front, beach and pool table

LaPointe
With a stay at this vacation home in La Pointe, you'll be on a lake, just steps from Lake Superior and a 3-minute drive from Big Bay State Park.
SUMMER SPECIALS Beautiful lake front, beach and pool table
Lake Shore Home with private dock and large deck--1 mile from Bayfield

Lake Shore Home with private dock and large deck--1 mile from Bayfield

Bayfield
With a stay at this vacation home in Bayfield, you'll be on the waterfront, just steps from Lake Superior and a 3-minute drive from Madeline Island Ferry ...
Lake Shore Home with private dock and large deck--1 mile from Bayfield
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.

This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.

Herbster
Located in Herbster, this vacation home is on the waterfront, a 1-minute drive from Lake Superior and 6 minutes from Bark Bay Slough State Natural Area.
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!

This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!

Herbster
Located in Herbster, this vacation home is on a lake, a 2-minute drive from Lake Superior and 10 minutes from Boreal Forest.
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
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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
106 Holiday Homes
Lowest Price
AU$122
Highest Price
AU$666
Popular accommodation
300' of Private Beach, Motisi's Sandy Beach, Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails, Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities., 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit, SUMMER SPECIALS Beautiful lake front, beach and pool table, Lake Shore Home with private dock and large deck--1 mile from Bayfield, This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI., This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!

Top trending hotels in Chequamegon Bay

Quality Inn Ashland - Lake Superior

Quality Inn Ashland - Lake Superior

2.5 out of 5
30600 Us Highway 2, Ashland, WI
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 8 Dec to 9 Dec
AU$122
includes taxes & fees
8 Dec - 9 Dec
A stay at Quality Inn Ashland - Lake Superior places you in the heart of Ashland, steps from Lake Superior and 15 minutes by foot from Maslowski Beach.
Quality Inn Ashland - Lake Superior
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 AU$170 per night from 23 Nov to 24 Nov
AU$170
includes taxes & fees
23 Nov - 24 Nov
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
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 15 Dec to 16 Dec
AU$174
includes taxes & fees
15 Dec - 16 Dec
With a stay at AmericInn by Wyndham Ashland in Ashland, you'll be next to a golf course, just steps from Lake Superior and a 5-minute drive from Ashland Mural ...
AmericInn by Wyndham Ashland
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Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

2.5 out of 5
818 Main Street W., Ashland, WI
Fully refundableReserve now, pay when you stay
The price is AU$239 per night from 23 Nov to 24 Nov
AU$239
includes taxes & fees
23 Nov - 24 Nov
A stay at Cobblestone Inn & Suites - Ashland places you in the heart of Ashland, steps from Ashland Mural Walk and Lake Superior.
Cobblestone Inn & Suites - Ashland
Don't see what you're looking for?
See all available properties in Chequamegon Bay
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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.

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^Subject to availability and chosen travel dates.