Book Holiday Homes in Baileys Harbor

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Featured Holiday Homes in Baileys Harbor

The Cherry Cabana- Sister Bay

The Cherry Cabana- Sister Bay

Sister Bay
With a stay at this vacation home in Sister Bay, you'll be within a 15-minute walk of Lake Michigan and Pirate's Cove Adventure Golf.
The Cherry Cabana- Sister Bay
Beautiful Door County Waterfront Property - Fall Dates Available

Beautiful Door County Waterfront Property - Fall Dates Available

Sturgeon Bay
When you stay at this vacation home in Sturgeon Bay, you'll be on the waterfront, just steps from Lake Michigan and a 5-minute drive from Bay Shore Blufflands ...
Beautiful Door County Waterfront Property - Fall Dates Available
Country Estate! Pool, Game Room, Sauna

Country Estate! Pool, Game Room, Sauna

Sturgeon Bay
The price is AU$2,884 per night from 1 Jan to 2 Jan
AU$2,884
includes taxes & fees
1 Jan - 2 Jan 2025
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.
Country Estate! Pool, Game Room, Sauna
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Downtown Sturg - Arcades/Theater/Modern

Downtown Sturg - Arcades/Theater/Modern

Sturgeon Bay
The price is AU$796 per night from 2 Jan to 3 Jan
AU$796
includes taxes & fees
2 Jan - 3 Jan 2025
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.
Downtown Sturg - Arcades/Theater/Modern
BRAND NEW! Newly Constructed home, walking distance to downtown Fish Creek!

BRAND NEW! Newly Constructed home, walking distance to downtown Fish Creek!

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 School of Art.
BRAND NEW! Newly Constructed home, walking distance to downtown Fish Creek!
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!
Whispering Pines By The Bay, quiet seclusion near water and town

Whispering Pines By The Bay, quiet seclusion near water and town

Sturgeon Bay
Located in Sturgeon Bay, this vacation home is in a rural location, a 4-minute drive from Crossroads At Big Creek and 6 minutes from Sturgeon Bay Ship Canal ...
Whispering Pines By The Bay, quiet seclusion near water and town
Breathtaking views on the Bay! Waterfrontage!

Breathtaking views on the Bay! Waterfrontage!

Sturgeon Bay
With a stay at this vacation home in Sturgeon Bay, you'll be on the waterfront, within a 10-minute drive of Lake Michigan and Third Avenue Playhouse.
Breathtaking views on the Bay! Waterfrontage!
New! Beautiful newly built family home immersed in nature. Fish Creek, WI

New! Beautiful newly built family home immersed in nature. Fish Creek, WI

Fish Creek
With a stay at this vacation home in Fish Creek, you'll be within a 10-minute drive of Lake Michigan and The Skyway Drive-In Theatre.
New! Beautiful newly built family home immersed in nature. Fish Creek, WI
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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
308 Holiday Homes
Lowest Price
AU$796
Highest Price
AU$2,884
Popular accommodation
The Cherry Cabana- Sister Bay, Beautiful Door County Waterfront Property - Fall Dates Available, Country Estate! Pool, Game Room, Sauna, Downtown Sturg - Arcades/Theater/Modern, BRAND NEW! Newly Constructed home, walking distance to downtown Fish Creek! , Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!, Whispering Pines By The Bay, quiet seclusion near water and town, Breathtaking views on the Bay! Waterfrontage!, New! Beautiful newly built family home immersed in nature. Fish Creek, WI

Top trending hotels in Baileys Harbor

Ridges Inn & Suites

Ridges Inn & Suites

2.5 out of 5
8252 STH 57, Baileys Harbor, WI
When you stay at Ridges Inn & Suites in Baileys Harbor, you'll be near the beach, within a 15-minute walk of Lake Michigan and Baileys Harbor Ridges Park.
Ridges Inn & Suites
Beachfront Inn

Beachfront Inn

2 out of 5
8040 State Hwy 57, Baileys Harbor, WI
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
Gordon Lodge

Gordon Lodge

4 out of 5
1420 Pine Drive, Baileys Harbor, WI
With a stay at Gordon Lodge in Baileys Harbor, you'll be on the waterfront, within a 15-minute drive of Lake Michigan and Ridges Sanctuary.
Gordon Lodge
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Serene Lakefront Baileys Harbor Home w/ Deck!

Serene Lakefront Baileys Harbor Home w/ Deck!

Bailey's Harbor
When you stay at this vacation home in Baileys Harbor, you'll be on the waterfront, just steps from Lake Michigan and 5 minutes by foot from Cana Island ...
Serene Lakefront Baileys Harbor Home w/ Deck!
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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.