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

Baileys Harbor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Baileys Harbor holiday rentals

Fabulous 2 Bed, 2 Bath Cottage On Kangaroo Lake

Fabulous 2 Bed, 2 Bath Cottage On Kangaroo Lake
Baileys Harbor
9.6 out of 10, Exceptional, (47 reviews)
"So relaxing … the perfect peaceful getaway. "
United States
Victoria N J.
The price is NZ$2,696
includes taxes & fees
2 July - 3 July
Fabulous 2 Bed, 2 Bath Cottage On Kangaroo Lake

Beautiful Home in Baileys Harbor

Beautiful Home in Baileys Harbor
Baileys Harbor
10.0 out of 10, Exceptional, (46 reviews)
"We had a wonderful time and home was perfect! Owners were very friendly and nice."
United States
Denise Z.
Beautiful Home in Baileys Harbor

Rustic Log Home located near Baileys Harbor

Rustic Log Home located near Baileys Harbor
Baileys Harbor
10.0 out of 10, Exceptional, (142 reviews)
"Beautiful log cabin with a cozy fireplace. The kitchen was fully stocked and a great size for our family. "
United States
Amy D.
The price is NZ$1,499
includes taxes & fees
15 July - 16 July
Rustic Log Home located near Baileys Harbor

30' CARVER BOAT DOCKED AT MENOMINEE MARINA IN HISTORIC DOWNTOWN MENOMINE MI.

30' CARVER BOAT DOCKED AT MENOMINEE MARINA IN HISTORIC DOWNTOWN MENOMINE MI.
Menominee
9.6 out of 10, Exceptional, (25 reviews)
The price is NZ$420
includes taxes & fees
8 July - 9 July
30' CARVER BOAT DOCKED AT MENOMINEE MARINA IN HISTORIC DOWNTOWN MENOMINE MI.

Beautiful yacht for rent with 4 beds, kitchen, grill, 4 tvs, internet, ac

Beautiful yacht for rent with 4 beds, kitchen, grill, 4 tvs, internet, ac
Sturgeon Bay
10.0 out of 10, Exceptional, (2 reviews)
"Amazing yacht stay! Perfect description. Had an amazing time. Communication with host was great, any questions I had were answered quickly. Will definitely be starting here any time in I'm in Saint Pete. 5 stars, highly recommend "
United States
Daniel W.
The price is NZ$533
includes taxes & fees
29 June - 30 June
Beautiful yacht for rent with 4 beds, kitchen, grill, 4 tvs, internet, ac

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, (43 reviews)
"Good stay. Nice place. Glad it had a garage weather was all over the place."
United States
Aaron M.
The price is NZ$434
includes taxes & fees
30 June - 1 July
Cozy Door County home with detached yoga room- short walk from Potawatomi Park

Updated Home w/ Deck: 2 Mi to Sister Bay Beach!

Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
Sister Bay
9.8 out of 10, Exceptional, (52 reviews)
"We stayed here with four adults and three kids under the age of 4 and there was plenty of room for everyone. The kids really enjoyed the large deck in the back. The half bath was located in a bedroom but we made it work. The property is beautiful and very close to Sister Bay. We would definitely stay here again."
United States
Jesse S.
The price is NZ$763
includes taxes & fees
5 July - 6 July
Updated Home w/ Deck: 2 Mi to Sister Bay Beach!

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, (58 reviews)
"Fantastic property - was perfect for our family of 5."
United States
Andrew L.
The price is NZ$1,498
includes taxes & fees
8 July - 9 July
Private 3BR Gem on 2.5 Wooded Acres- Close to All

Door County Home Away - Backyard Seclusion, Close to Beaches, Shops, Restaurants

Door County Home Away - Backyard Seclusion, Close to Beaches, Shops, Restaurants
Sturgeon Bay
9.6 out of 10, Exceptional, (74 reviews)
"Excellent property to stay at. Very clean, well supplied with the basics."
United States
Tanya H.
The price is NZ$793
includes taxes & fees
28 June - 29 June
Door County Home Away - Backyard Seclusion, Close to Beaches, Shops, Restaurants

Door County Cabin on the Water

Door County Cabin on the Water
Sturgeon Bay
9.2 out of 10, Wonderful, (46 reviews)
"Very clean and great location!"
United States
Katelyn C.
The price is NZ$772
includes taxes & fees
1 July - 2 July
Door County Cabin on the Water

Nautical Haven - Sunset views

Nautical Haven - Sunset views
Sturgeon Bay
9.8 out of 10, Exceptional, (30 reviews)
"Check in was easy. The accommodations were great! Highly recommend!"
United States
Cheryl R.
The price is NZ$906
includes taxes & fees
5 July - 6 July
Nautical Haven - Sunset views

Snug Harbor Inn - 2 Bedroom Cottage

Snug Harbor Inn - 2 Bedroom Cottage
Sturgeon Bay
9.2 out of 10, Wonderful, (60 reviews)
"Great location and a pretty view."
United States
Nicholas N.
Snug Harbor Inn - 2 Bedroom Cottage

Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (958 reviews)
"Beautiful place to stay"
United States
Zohra
The price is NZ$683
includes taxes & fees
29 June - 30 June
Westwood Shores Waterfront Resort

Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (74 reviews)
"Good location, good hotel. "
United States
shane
The price is NZ$634
includes taxes & fees
30 June - 1 July
Evergreen Hill Condominiums

Walk to Downtown! Wooded 4BR Sister Bay Home

Walk to Downtown! Wooded 4BR Sister Bay Home
Sister Bay
9.8 out of 10, Exceptional, (27 reviews)
"Nice clean property close to town."
United States
Nicole H.
The price is NZ$1,012
includes taxes & fees
29 June - 30 June
Walk to Downtown! Wooded 4BR Sister Bay Home

The Doorgeous Tamarack Cabin

The Doorgeous Tamarack Cabin
Sturgeon Bay
10.0 out of 10, Exceptional, (1 review)
"My wife and I were looking forward to this weekend getaway. A very cozy well tastefully decorated cabin. The Christmas tree was a pleasant surprise. Eack morning we had a hot breakfast delivered and a couple of tastefull chocolate chip cookies were on a plate for us when we came back from our daily activities. A very nice getaway, thanks Bryon and Nick!"
United States
Jonathan S.
The price is NZ$860
includes taxes & fees
28 June - 29 June
The Doorgeous Tamarack Cabin

Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (607 reviews)
"Friendly staff, very clean and very nice rooms!"
United States
Sonia
The price is NZ$472
includes taxes & fees
30 June - 1 July
Bridgeport Waterfront Resort

A Charming Door County Condo in the heart of Sturgeon Bay

A Charming Door County Condo in the heart of Sturgeon Bay
Sturgeon Bay
8.8 out of 10, Excellent, (3 reviews)
"Everything was great, Beautiful Home, great neighborhood, had a wonderfull trip, will definitely book another stay in the future, Kelly was awesome "
United States
Angela M.
A Charming Door County Condo in the heart of Sturgeon Bay

Location! Walk to Downtown - Garden Studio Apt. in the Heart of Door County!

Location! Walk to Downtown - Garden Studio Apt. in the Heart of Door County!
Sturgeon Bay
10.0 out of 10, Exceptional, (25 reviews)
"Great property, reasonably priced, super friendly owners. Will definitely stay here again."
United States
Matt F.
The price is NZ$432
includes taxes & fees
26 July - 27 July
Location! Walk to Downtown - Garden Studio Apt. in the Heart of Door County!

Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (500 reviews)
"Lovely stay."
United States
Susan
The price is NZ$613
includes taxes & fees
30 June - 1 July
Waterbury Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Baileys Harbor Hotel Reviews

Find out more about Baileys Harbor

Everything you need to know about Baileys Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Baileys Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Baileys Harbor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Baileys Harbor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Baileys Harbor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Baileys Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Baileys Harbor holiday rentals we have selected for you start as low as NZ$472 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Baileys Harbor rentals

At Expedia, we put the best Baileys Harbor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Baileys Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Baileys Harbor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Baileys Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Baileys Harbor?

Yes, there are holiday rentals close to the most popular sights in Baileys Harbor, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Baileys Harbor speak positively about the scenic lakeside and top-notch restaurants in this destination. Allow some time to check out the shops during your trip.

What are some of the best holiday rentals that Baileys Harbor has to offer?

Stunning Lakefront 5BR 5000 sq ft Dune Alright: This highly rated holiday home rental in Baileys Harbor is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Baileys Harbor is Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!.

How many holiday rentals will I find in Baileys Harbor?

Expedia has 69 holiday rentals for your stay in Baileys Harbor.

What can I see and do in Baileys Harbor?

Lake Michigan and Anclam Beach Park are a couple of scenic spots to enjoy the outdoors, whereas Door Shakespeare is one of the cultural attractions. Door County Brewing Company and Cana Island Lighthouse are other places to visit while you're in town.

What are holiday rentals like in Baileys Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Baileys Harbor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.