Book Holiday Homes in Baileys Harbor

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Featured Holiday Homes in Baileys Harbor

Indoor Pool, Game RM, Movie RM! Sleep 24! Private!

Indoor Pool, Game RM, Movie RM! Sleep 24! Private!

Sturgeon Bay
With a stay at this vacation home in Sturgeon Bay, you'll be on a lake, within a 10-minute drive of Lake Michigan and Snake Island.
Indoor Pool, Game RM, Movie RM! Sleep 24! Private!
Home w/ Fireplace < 1 Mi to Peninsula State Park!

Home w/ Fireplace < 1 Mi to Peninsula State Park!

Fish Creek
With a stay at this vacation home in Fish Creek, you'll be within a 5-minute drive of Lake Michigan and Peninsula State Park.
Home w/ Fireplace < 1 Mi to Peninsula State Park!
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

Baileys Harbor
When you stay at this vacation home in Baileys Harbor, you'll be on the beach, just steps from Lake Michigan and a 4-minute drive from Cana Island ...
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!
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Sister Bay Vintage Log Cabin

Sister Bay Vintage Log Cabin

Sister Bay
With a stay at this vacation home in Sister Bay, you'll be a 1-minute walk from Lake Michigan and 6 minutes by foot from Sister Bay Marina.
Sister Bay Vintage Log Cabin
The Quilted Log, a cozy, compact cabin In the woods, very clean, perfect for 4-6

The Quilted Log, a cozy, compact cabin In the woods, very clean, perfect for 4-6

Sturgeon Bay
Located in Sturgeon Bay, this vacation home is in a rural location, within a 10-minute drive of Plum Loco Animal Farm and Clark Lake.
The Quilted Log, a cozy, compact cabin In the woods, very clean, perfect for 4-6
Beautiful updated house on Lake Michigan in the heart of downtown Baileys Harbor

Beautiful updated house on Lake Michigan in the heart of downtown Baileys Harbor

Baileys Harbor
With a stay at this vacation home, you'll be centrally located in Baileys Harbor, steps from Lake Michigan and 3 minutes by foot from Anclam Beach Park.
Beautiful updated house on Lake Michigan in the heart of downtown Baileys Harbor
Peaceful cul-de-sac and Walking Distance to Sister Bay

Peaceful cul-de-sac and Walking Distance to Sister Bay

Sister Bay
When you stay at this vacation home in Sister Bay, you'll be near the beach, within a 15-minute walk of Lake Michigan and Sister Bay Marina.
Peaceful cul-de-sac and Walking Distance to Sister Bay
Roomy House on 2 Acres - 2 Mi to Egg Harbor Beach!

Roomy House on 2 Acres - 2 Mi to Egg Harbor Beach!

Egg Harbor
With a stay at this vacation home in Egg Harbor, you'll be within a 10-minute drive of Lake Michigan and The Orchards at Egg Harbor.
Roomy House on 2 Acres - 2 Mi to Egg Harbor Beach!
Cool + Modern! Arcades, Movie RM, Private Pond!

Cool + Modern! Arcades, Movie RM, Private Pond!

Sturgeon Bay
With a stay at this vacation home in Sturgeon Bay, you'll be near the beach, within a 10-minute drive of Lake Michigan and Crossroads At Big Creek.
Cool + Modern! Arcades, Movie RM, Private Pond!
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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.

Baileys Harbor 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 Baileys Harbor vacation homes are the perfect way for you to wing it.

Holiday houses in Baileys Harbor 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 Baileys Harbor 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 Baileys Harbor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Baileys Harbor 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 Baileys Harbor 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.

Baileys Harbor Holiday Homes essential information

Accommodation
417 Holiday Homes
Lowest Price
AU$181
Highest Price
AU$181
Popular accommodation
Indoor Pool, Game RM, Movie RM! Sleep 24! Private!, Home w/ Fireplace < 1 Mi to Peninsula State Park!, Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!, Sister Bay Vintage Log Cabin, The Quilted Log, a cozy, compact cabin In the woods, very clean, perfect for 4-6, Beautiful updated house on Lake Michigan in the heart of downtown Baileys Harbor, Peaceful cul-de-sac and Walking Distance to Sister Bay, Roomy House on 2 Acres - 2 Mi to Egg Harbor Beach!, Cool + Modern! Arcades, Movie RM, Private Pond!

Top trending hotels in Baileys Harbor

Beachfront Inn

Beachfront Inn

2 out of 5
8040 State Hwy 57, Baileys Harbor, WI
The price is AU$181 per night from 27 Apr to 28 Apr
AU$181
includes taxes & fees
27 Apr - 28 Apr
When you stay at Beachfront Inn in Baileys Harbor, you'll be on the waterfront, just steps from Lake Michigan and 6 minutes by foot from Anclam Beach Park.
Beachfront Inn
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

Baileys Harbor
When you stay at this vacation home in Baileys Harbor, you'll be on the beach, just steps from Lake Michigan and a 4-minute drive from Cana Island ...
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!
Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!

Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!

Baileys Harbor
When you stay at this vacation home in Baileys Harbor, you'll be on the beach, just steps from Lake Michigan and Anclam Beach Park.
Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!
Save an average of 15% on thousands of hotels when you're signed in
Cute Cottage - Center of the Door Peninsula - Pet Friendly!
On Snowmobile Trail!

Cute Cottage - Center of the Door Peninsula - Pet Friendly! On Snowmobile Trail!

Baileys Harbor
With a stay at this vacation home in Baileys Harbor, you'll be within a 15-minute drive of Lake Michigan and Stone's Throw Winery.
Cute Cottage - Center of the Door Peninsula - Pet Friendly! On Snowmobile Trail!
Don't see what you're looking for?
See all available properties in Baileys Harbor
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.