Book Holiday Homes in Baileys Harbor

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Featured Holiday Homes in Baileys Harbor

Sister Bay Log Cabin - Recent Remodel!

Sister Bay Log Cabin - Recent Remodel!

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 Log Cabin - Recent Remodel!
Welcome to your own private getaway!

Welcome to your own private getaway!

Sister Bay
When you stay at this vacation home in Sister Bay, you'll be on a lake, just steps from Lake Michigan and 10 minutes by foot from Bay Ridge Golf Course.
Welcome to your own private getaway!
Harbor House - Prime June dates just became available!

Harbor House - Prime June dates just became available!

Ephraim
When you stay at this vacation home in Ephraim, you'll be on a lake, within a 5-minute walk of Lake Michigan and Eagle Harbor.
Harbor House - Prime June dates just became available!
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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!
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!
Charming guesthouse within minutes of downtown Fish Creek!

Charming guesthouse within minutes of 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 Historic Noble House.
Charming guesthouse within minutes of downtown Fish Creek!
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
Pinecone Haven - Where Northwoods meets the Southwest

Pinecone Haven - Where Northwoods meets the Southwest

Sturgeon Bay
With a stay at this vacation home in Sturgeon Bay, you'll be within a 15-minute walk of Door County Maritime Museum and Sturgeon Bay Bridge.
Pinecone Haven - Where Northwoods meets the Southwest
Spacious Family-Friendly Cottage on 7.5 acre peaceful wooded area

Spacious Family-Friendly Cottage on 7.5 acre peaceful wooded area

Ellison Bay
With a stay at this vacation home in Ellison Bay, you'll be a 3-minute drive from Lake Michigan and 6 minutes from Linden Gallery.
Spacious Family-Friendly Cottage on 7.5 acre peaceful wooded area
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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
451 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Sister Bay Log Cabin - Recent Remodel!, Welcome to your own private getaway!, Harbor House - Prime June dates just became available!, Indoor Pool, Game RM, Movie RM! Sleep 24! Private!, Cool + Modern! Arcades, Movie RM, Private Pond!, Charming guesthouse within minutes of downtown Fish Creek!, The Quilted Log, a cozy, compact cabin In the woods, very clean, perfect for 4-6, Pinecone Haven - Where Northwoods meets the Southwest , Spacious Family-Friendly Cottage on 7.5 acre peaceful wooded area

Top trending hotels in Baileys Harbor

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
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
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!
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Scandinavian Lodge

Scandinavian Lodge

3.5 out of 5
10506 State HWY 57, Sister Bay, WI
When you stay at Scandinavian Lodge in Sister Bay, you'll be near the beach, within a 15-minute walk of Lake Michigan and Waterfront Park.
Scandinavian Lodge
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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.