An aerial view of a coastal island with a mix of residential areas, green spaces, and rocky coastlines.

Holiday Homes in Baileys Harbor

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Baileys Harbor holiday homes

A two-story house with a wrap-around porch, a turret, and a front door with an American flag.

1. Private 3BR Gem on 2.5 Wooded Acres- Close to All

Private 3BR Gem on 2.5 Wooded Acres- Close to All
Sister Bay
10.0 out of 10, Exceptional, (61 reviews)
"Fantastic property - was perfect for our family of 5."
United States
Andrew L.
The price is NZ$908
includes taxes & fees
22 Nov - 23 Nov
Private 3BR Gem on 2.5 Wooded Acres- Close to All
A white arched entrance with a dark green door, surrounded by greenery and a pathway leading to a porch.

2. THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
Ephraim
9.8 out of 10, Exceptional, (94 reviews)
"Super cozy cottage just a short drive from town. Adorable courtyard with great landscaping. A perfect getaway for my mom and I to visit Door County!"
United States
Kayla V.
The price is NZ$607
includes taxes & fees
1 Nov - 2 Nov
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
A backyard with two blue Adirondack chairs, a fire pit, and a house in the background.

3. Walk to Downtown! Wooded 4BR Sister Bay Home

Walk to Downtown! Wooded 4BR Sister Bay Home
Sister Bay
9.6 out of 10, Exceptional, (30 reviews)
"Nice clean property close to town."
United States
Nicole H.
The price is NZ$936
includes taxes & fees
9 Nov - 10 Nov
Walk to Downtown! Wooded 4BR Sister Bay Home
A modern cabin with a wooden exterior, surrounded by a forest and snow-covered ground.

4. Cedar & Glass | Modern Architectural Retreat

Cedar & Glass | Modern Architectural Retreat
Fish Creek
9.6 out of 10, Exceptional, (5 reviews)
"A thoughtfully designed and curated home with top end amenities. We stayed for 3 nights and loved the serenity of the setting and space. The house has gorgeous showers, a gas fireplace and fun games to play. Loved being able to make all kinds of coffee drinks on the espresso machine. Perfect place to stay and enjoy nature and decompress. Highly recommended!!!"
United States
katherine k.
The price is NZ$1,589
includes taxes & fees
26 Oct - 27 Oct
Cedar & Glass | Modern Architectural Retreat
A two-story house with a front porch, a garage, and a landscaped garden with various plants and flowers.

5. A Truly Luxurious Door County Retreat

A Truly Luxurious Door County Retreat
Fish Creek
9.6 out of 10, Exceptional, (23 reviews)
"Impressive home, expansive yard, good location, friendly neighbor."
United States
Alan V.
The price is NZ$2,498
includes taxes & fees
25 Oct - 26 Oct
A Truly Luxurious Door County Retreat
A modern kitchen with white cabinets, stainless steel appliances, a large island with bar stools, and pendant lighting.

6. Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay

Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay
Ellison Bay
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely beautiful property! We have nothing but great things to say about it. Stylish and comfortable with everything you could want in a door county getaway. Close to a lot of our favorite DC place’s & restaurants. Host is wonderful to work with, really goes the extra mile. We hope to stay again!"
United States
Rebecca U.
The price is NZ$1,111
includes taxes & fees
6 Nov - 7 Nov
Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay
Terrace/patio

7. Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay

Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
Ellison Bay
10.0 out of 10, Exceptional, (32 reviews)
"The house was clean and very comfortable! Everything we could have wanted was there- we discovered the drawer in the coffee table with games on night three:)Loved walking into Ellison Bay for dinner, sunsets and morning coffee.Will definitely stay here again!!"
United States
Molly C.
The price is NZ$1,203
includes taxes & fees
22 Nov - 23 Nov
Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
A porch with a wicker swing chair, a white table, and a potted plant.

8. Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach

Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
Ellison Bay
10.0 out of 10, Exceptional, (32 reviews)
"Amazing place to stay! Has everything you need for a nice family/friends vacation getaway! We loved it!"
United States
Deanna W.
The price is NZ$1,317
includes taxes & fees
9 Nov - 10 Nov
Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
A dining area with a round glass table and two chairs, a potted plant, and a view of a street through a window with blinds.

9. Cozy Door County home with detached yoga room- short walk from Potawatomi Park

Cozy Door County home with detached yoga room- short walk from Potawatomi Park
Sturgeon Bay
10.0 out of 10, Exceptional, (58 reviews)
"Location is good. Easy bike ride to potawami State Park and downtown sturgeon Bay. It is on highway C which does get a bit of traffic but we didn't notice with the windows closed. The shower is small but functional. The two-car garage is great for storing our e-bikes. We had a very good stay. Price was very good and much nicer staying here than in the hotel."
United States
MARK w
The price is NZ$398
includes taxes & fees
4 Nov - 5 Nov
Cozy Door County home with detached yoga room- short walk from Potawatomi Park
A spacious dining area with a long wooden table, white chairs, and a kitchen in the background.

10. Groups! HotTub! Huge Yard! Bikes/Kayaks/Games!

Groups! HotTub! Huge Yard! Bikes/Kayaks/Games!
Ephraim
9.8 out of 10, Exceptional, (54 reviews)
"Very nice set up for a multi age group."
United States
Alice B.
The price is NZ$3,419
includes taxes & fees
25 Oct - 26 Oct
Groups! HotTub! Huge Yard! Bikes/Kayaks/Games!
A bedroom with a bed, a ceiling fan, a window with curtains, and a nightstand with a lamp.

11. 2BR Home Near Marinas / Ideal for Work or Fishing

2BR Home Near Marinas / Ideal for Work or Fishing
Marinette
The price is NZ$470
includes taxes & fees
10 Nov - 11 Nov
2BR Home Near Marinas / Ideal for Work or Fishing
A cozy living room with a stone fireplace, wooden paneling, a comfortable armchair, and a bookshelf filled with books and decorative items.

12. Door County Cabin on the Water

Door County Cabin on the Water
Sturgeon Bay
9.0 out of 10, Wonderful, (51 reviews)
"Beautiful view of water!"
United States
Adam C.
The price is NZ$542
includes taxes & fees
3 Nov - 4 Nov
Door County Cabin on the Water
A modern kitchen with a large island, bar stools, stainless steel appliances, and wooden cabinets.

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

Indoor Pool, Game RM, Movie RM! Sleep 24! Private!
Sturgeon Bay
9.8 out of 10, Exceptional, (99 reviews)
"Wonderful location and spot for big families or friends to gather. There's plently of space for everyone and tons of activities to keep everyone busy and engaged."
United States
Renee N.
Indoor Pool, Game RM, Movie RM! Sleep 24! Private!
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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Top Baileys Harbor Hotel Reviews

Homestead Suites

Homestead Suites

8/10 Good
"No thanks"
Richard 3-night trip
Posted 3 hours ago
Homestead Suites

Find out more about Baileys Harbor

Baileys Harbor Holiday Homes information

Number of reviews
375
Accommodation
498 Holiday Homes
Lowest Price
NZ$398
Highest Price
NZ$3,419