Book Holiday Homes in Baileys Harbor

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Featured Holiday Homes in Baileys Harbor

SPECTACULAR WATER VIEWS on the bluff. Secluded. Quiet.

SPECTACULAR WATER VIEWS on the bluff. Secluded. Quiet.

Fish Creek WI
With a stay at this vacation home in Fish Creek, you'll be on a lake, within a 5-minute drive of Lake Michigan and Edgewood Orchard Galleries.
Opens in a new windowSPECTACULAR WATER VIEWS on the bluff. Secluded. Quiet.
Historic Remodeled 1938 Log Cabin – Walk to Sister Bay

Historic Remodeled 1938 Log Cabin – Walk to Sister Bay

Sister Bay WI
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.
Opens in a new windowHistoric Remodeled 1938 Log Cabin – Walk to Sister Bay
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

Ephraim WI
The price is AU$435 per night from 14 Apr to 15 Apr
AU$435
14 Apr - 15 Apr
includes taxes & fees
Located in Ephraim, this vacation home is in a rural location, within a 5-minute drive of Eagle Harbor and Lake Michigan.
Opens in a new windowTHE CHARM of DOOR COUNTY - Cuteness and elegance combined!
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Top-Rated 6-Bedroom Vacation Home in Sister Bay – Walkable & Family-Friendly

Top-Rated 6-Bedroom Vacation Home in Sister Bay – Walkable & Family-Friendly

Sister Bay WI
A stay at this vacation home places you in the heart of Sister Bay, within a 15-minute walk of Lake Michigan and Pirate's Cove Adventure Golf.
Opens in a new windowTop-Rated 6-Bedroom Vacation Home in Sister Bay – Walkable & Family-Friendly
House By The Bay| Cedar Hot Tub & Sauna

House By The Bay| Cedar Hot Tub & Sauna

sturgeon bay WI
Located in Sturgeon Bay, this vacation home is on a lake, within a 15-minute walk of Door County Maritime Museum and Sturgeon Bay Bridge.
Opens in a new windowHouse By The Bay| Cedar Hot Tub & Sauna
Clay  Banks  Retreat

Clay Banks Retreat

Sturgeon Bay WI
Located in Sturgeon Bay, this vacation home is in a rural location, a 3-minute drive from Lake Michigan and 5 minutes from Legacy Nature Preserve at Clay ...
Opens in a new windowClay Banks Retreat
Catch an Early Spring Get Away in a Brand New 2-bedroom home in Baileys Harbor

Catch an Early Spring Get Away in a Brand New 2-bedroom home in Baileys Harbor

Baileys Harbor WI
With a stay at this vacation home in Baileys Harbor, you'll be within a 15-minute walk of Lake Michigan and Door County Brewing Company.
Opens in a new windowCatch an Early Spring Get Away in a Brand New 2-bedroom home in Baileys Harbor
The Maxwell on 4th — 3 BR home in Door County near marina, shops & restaurants

The Maxwell on 4th — 3 BR home in Door County near marina, shops & restaurants

Sturgeon Bay WI
The price is AU$440 per night from 20 Mar to 21 Mar
AU$440
20 Mar - 21 Mar
includes taxes & fees
With a stay at this vacation home in Sturgeon Bay, you'll be within a 15-minute drive of Lake Michigan and Miller Art Museum.
Opens in a new windowThe Maxwell on 4th — 3 BR home in Door County near marina, shops & restaurants
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 WI
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 ...
Opens in a new windowLake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!
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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
426 Holiday Homes
Lowest Price
AU$435
Highest Price
AU$440
Popular accommodation
SPECTACULAR WATER VIEWS on the bluff. Secluded. Quiet., Historic Remodeled 1938 Log Cabin – Walk to Sister Bay, THE CHARM of DOOR COUNTY - Cuteness and elegance combined!, Top-Rated 6-Bedroom Vacation Home in Sister Bay – Walkable & Family-Friendly, House By The Bay| Cedar Hot Tub & Sauna, Clay Banks Retreat, Catch an Early Spring Get Away in a Brand New 2-bedroom home in Baileys Harbor, The Maxwell on 4th — 3 BR home in Door County near marina, shops & restaurants, Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

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.
Opens in a new windowGordon Lodge
250'  RELAXING WATERFRONT SPACIOUS REMODEL & WALKING TO SAND BEACH NEW FIREPLACE

250' RELAXING WATERFRONT SPACIOUS REMODEL & WALKING TO SAND BEACH NEW FIREPLACE

Baileys Harbor WI
When you stay at this vacation home in Baileys Harbor, you'll be on the waterfront, just steps from Lake Michigan and a 3-minute drive from Cana Island ...
Opens in a new window250' RELAXING WATERFRONT SPACIOUS REMODEL & WALKING TO SAND BEACH NEW FIREPLACE
Luxury lakefront home - 6 BRs, kids, pets, EVs, elevator - family celebrations

Luxury lakefront home - 6 BRs, kids, pets, EVs, elevator - family celebrations

Baileys Harbor WI
When you stay at this vacation home in Baileys Harbor, you'll be on the beach, just steps from Lake Michigan and 5 minutes by foot from Cana Island ...
Opens in a new windowLuxury lakefront home - 6 BRs, kids, pets, EVs, elevator - family celebrations
Save an average of 15% on thousands of hotels when you're signed in
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.
Opens in a new windowScandinavian Lodge
Don't see what you're looking for?
See all available properties in Baileys Harbor
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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.

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