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
Stay at this vacation home in Sister Bay. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Sister Bay Marina and Waterfront Park ...
Opens in a new windowSister Bay Log Cabin - Recent Remodel!
Welcome to your own private getaway!

Welcome to your own private getaway!

Sister Bay
Stay at this vacation home in Sister Bay. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bay Ridge Golf Course and Frykman Studio Gallery ...
Opens in a new windowWelcome to your own private getaway!
8 Miles Of Sand Beach To Explore ~ Outstanding Sunset Views Over The Lake!

8 Miles Of Sand Beach To Explore ~ Outstanding Sunset Views Over The Lake!

Sturgeon Bay
Book a stay at this beach vacation home in Sturgeon Bay. Enjoy free WiFi, a beach locale, and a water park. Popular attractions The Farm and The Garden Door ...
Opens in a new window8 Miles Of Sand Beach To Explore ~ Outstanding Sunset Views Over The Lake!
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Cute Cottage - Center of the Door Peninsula - Pet Friendly!

Cute Cottage - Center of the Door Peninsula - Pet Friendly!

Baileys Harbor
Stay at this vacation home in Baileys Harbor. Enjoy free WiFi, a garden, and patios. Popular attractions Stone's Throw Winery and Birch Creek Music Performance ...
Opens in a new windowCute Cottage - Center of the Door Peninsula - Pet Friendly!
Guest bedroom in Quarry House

Guest bedroom in Quarry House

Fish Creek
Stay at this vacation home in Fish Creek. Enjoy a sauna, a garden, and patios. Popular attractions Edgewood Orchard Galleries and Hands On Art Studio are located ...
Opens in a new windowGuest bedroom in Quarry House
Stunning Frank Lloyd Wright inspired vacation house in Sister Bay Great Location

Stunning Frank Lloyd Wright inspired vacation house in Sister Bay Great Location

Sister Bay
Stay at this vacation home in Sister Bay. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Pirate's Cove Adventure Golf and Frykman Studio ...
Opens in a new windowStunning Frank Lloyd Wright inspired vacation house in Sister Bay Great Location
Charming guesthouse within minutes of downtown Fish Creek!

Charming guesthouse within minutes of downtown Fish Creek!

Fish Creek
Book a stay at this family-friendly vacation home in Fish Creek. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Historic ...
Opens in a new windowCharming guesthouse within minutes of downtown Fish Creek!
Washington Island - West side shore front home!

Washington Island - West side shore front home!

Washington
Stay at this vacation home in Washington Island. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Schoolhouse Beach Park and Deer Run ...
Opens in a new windowWashington Island - West side shore front home!
Wild Cedars - Cana Island - Lake Michigan - Amazing new home

Wild Cedars - Cana Island - Lake Michigan - Amazing new home

Baileys Harbor
Book a stay at this beach vacation home in Baileys Harbor. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cana Island Lighthouse and Baileys ...
Opens in a new windowWild Cedars - Cana Island - Lake Michigan - Amazing new home
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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
463 Holiday Homes
Lowest Price
NZ$282
Highest Price
NZ$302
Popular accommodation
Sister Bay Log Cabin - Recent Remodel!, Welcome to your own private getaway!, 8 Miles Of Sand Beach To Explore ~ Outstanding Sunset Views Over The Lake! , Cute Cottage - Center of the Door Peninsula - Pet Friendly!, Guest bedroom in Quarry House, Stunning Frank Lloyd Wright inspired vacation house in Sister Bay Great Location, Charming guesthouse within minutes of downtown Fish Creek!, Washington Island - West side shore front home!, Wild Cedars - Cana Island - Lake Michigan - Amazing new home

Top trending hotels in Baileys Harbor

Gordon Lodge

Gordon Lodge

4 out of 5
1420 Pine Drive, Baileys Harbor, WI
The price is NZ$302 per night from 22 Sept to 23 Sept
NZ$302
22 Sept - 23 Sept
includes taxes & fees
Stay at this 4-star beach hotel in Baileys Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowGordon Lodge
Beachfront Inn

Beachfront Inn

2 out of 5
8040 State Hwy 57, Baileys Harbor, WI
The price is NZ$282 per night from 23 Sept to 24 Sept
NZ$282
23 Sept - 24 Sept
includes taxes & fees
Book a stay at this beach motel in Baileys Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowBeachfront 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
Book a stay at this family-friendly vacation home in Baileys Harbor. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Anclam Beach Park ...
Opens in a new windowWaterfront 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
Maxwelton Braes Lodge and Golf Course

Maxwelton Braes Lodge and Golf Course

2 out of 5
7670 Highway 57, Baileys Harbor, WI
Book a stay at this golf lodge in Baileys Harbor. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowMaxwelton Braes Lodge and Golf Course
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.