Aerial view of Bailey Beach and historic building the Waves on Ledge Road panorama at the end of Cliff Walk in city of Newport, Rhode Island RI, USA.

Baileys Harbor Vacation Rentals

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Our top choices for Baileys Harbor vacation rentals

Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
Baileys Harbor
10.0 out of 10, Exceptional, (99 reviews)
"Great stay with a good location"
United States
Michael S.
The price is CA $454
CA $902 total
includes taxes & fees
Jun 18 - Jun 19
Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

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 CA $710
CA $2,171 total
includes taxes & fees
Jun 13 - Jun 14
Fabulous 2 Bed, 2 Bath Cottage On Kangaroo Lake

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, (24 reviews)
"Hosts were great, great location , relaxing stay will definitely look into staying again!"
United States
Tim W.
The price is CA $234
CA $280 total
includes taxes & fees
Jun 13 - Jun 14
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 CA $188
CA $424 total
includes taxes & fees
Jun 14 - Jun 15
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, (42 reviews)
"Good stay. Nice place. Glad it had a garage weather was all over the place."
United States
Aaron M.
The price is CA $113
CA $351 total
includes taxes & fees
Jun 14 - Jun 15
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!
3.0 star property
Sister Bay
The price is CA $222
CA $581 total
includes taxes & fees
Jun 14 - Jun 15
Updated Home w/ Deck: 2 Mi to Sister Bay Beach!

Scandinavian Lodge

Scandinavian Lodge
3.5 star property
Sister Bay
9.4 out of 10, Exceptional, (1,582 reviews)
"The staff is very friendly, the resort is clean and comfortable. We loved our stay."
United States
Kathleen
Scandinavian Lodge

[Cozy] loft - steps to downtown!

[Cozy] loft - steps to downtown!
Sturgeon Bay
9.6 out of 10, Exceptional, (41 reviews)
"Excellent stay! Will definitely be recommending to others!"
United States
Autumn M.
The price is CA $103
CA $431 total
includes taxes & fees
Jun 24 - Jun 25
[Cozy] loft - steps to downtown!

Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (600 reviews)
"Friendly staff, very clean and very nice rooms!"
United States
Sonia
The price is CA $313
CA $371 total
includes taxes & fees
Jun 29 - Jun 30
Bridgeport Waterfront Resort

Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (955 reviews)
"Beautiful place to stay"
United States
Zohra
Westwood Shores Waterfront Resort

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

A City Cottage in the heart of Sturgeon Bay

A City Cottage in the heart of Sturgeon Bay
Sturgeon Bay
9.8 out of 10, Exceptional, (30 reviews)
"if you are looking for a cute place in the downtown of Sturgeon bay, walkable to all stores and the river, also, it was a good starting point to exploring Door county. "
United States
george
A City Cottage in the heart of Sturgeon Bay

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 CA $438
CA $903 total
includes taxes & fees
Jun 15 - Jun 16
Private 3BR Gem on 2.5 Wooded Acres- Close to All

Beach Harbor Resort - Studio Cottage

Beach Harbor Resort - Studio Cottage
Sturgeon Bay
7.6 out of 10, Good, (10 reviews)
"Property was tired, but fair for the price. "
United States
Amy
The price is CA $264
CA $353 total
includes taxes & fees
Jun 15 - Jun 16
Beach Harbor Resort - Studio Cottage

Door County Cabin on the Water

Door County Cabin on the Water
Sturgeon Bay
9.2 out of 10, Wonderful, (45 reviews)
"Very clean and great location!"
United States
Katelyn C.
The price is CA $212
CA $546 total
includes taxes & fees
Jun 14 - Jun 15
Door County Cabin on the Water

City Apartment | In the heart of historic downtown

City Apartment | In the heart of historic downtown
Sturgeon Bay
9.6 out of 10, Exceptional, (26 reviews)
"Kind host, and a cute and cozy space near everything. Property was well-stocked, clean, and quiet. Everything you could ask for!"
United States
Amanda S.
The price is CA $195
CA $478 total
includes taxes & fees
Jul 2 - Jul 3
City Apartment | In the heart of historic downtown

Newly updated cottage on 13 acres only minutes from Potawatomi State Park!

Newly updated cottage on 13 acres only minutes from Potawatomi State Park!
Sturgeon Bay
9.2 out of 10, Wonderful, (59 reviews)
"The stay was great! Andy was great to work with! Looking forward to coming back. "
United States
jordan G.
Newly updated cottage on 13 acres only minutes from Potawatomi State Park!

Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (495 reviews)
"Lovely stay."
United States
Susan
The price is CA $314
CA $383 total
includes taxes & fees
Jun 13 - Jun 14
Waterbury Inn

A Charming Door County Condo in the heart of Sturgeon Bay

A Charming Door County Condo in the heart of Sturgeon Bay
Sturgeon Bay
8.0 out of 10, Very good, (2 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.
The price is CA $152
CA $348 total
includes taxes & fees
Jun 14 - Jun 15
A Charming Door County Condo in the heart of Sturgeon Bay

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, (87 reviews)
"Very charming and quiet place to stay. Great location near town! "
United States
Tedra M.
The price is CA $375
CA $661 total
includes taxes & fees
Jun 15 - Jun 16
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
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

Find out more about Baileys Harbor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Baileys Harbor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Baileys Harbor?

Yes, we offer vacation rentals close to top attractions in Baileys Harbor, or you can select a secluded option if you'd like a relaxing place to 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 vacation home rentals that Baileys Harbor has to offer?

Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!: This highly rated vacation home rental in Baileys Harbor is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Baileys Harbor?

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

What can I see and do in Baileys Harbor?

Lake Michigan and Kangaroo Lake 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 vacation rentals like in Baileys Harbor?

Vacation rentals are privately owned properties you can stay in for several days or longer in Baileys Harbor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family gatherings.