Baileys Harbor Holiday Rentals

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Check prices for these dates

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Baileys Harbor holiday rentals

Front of property – evening/night
Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (924)
"Great resort with friendly staff!"
United States
Richard
The price is S$160
includes taxes & fees
4 Jan - 5 Jan, 2026
Westwood Shores Waterfront Resort
Property grounds
Bridgeport Waterfront Resort

Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (567)
"Great views and location "
United States
Richard
The price is S$208
includes taxes & fees
23 Dec - 24 Dec
Bridgeport Waterfront Resort
Exterior
Scandinavian Lodge

Scandinavian Lodge

Scandinavian Lodge
3.5 star property
Sister Bay
9.4 out of 10, Exceptional, (1556)
"Very clean, spacious room, friendly staff."
United States
David
Scandinavian Lodge
Restaurant
Landmark Resort

Landmark Resort

Landmark Resort
3.5 star property
Egg Harbor
9.0 out of 10, Wonderful, (609)
"Everything was great."
United States
DAVID
The price is S$221
includes taxes & fees
23 Dec - 24 Dec
Landmark Resort
Exterior
Evergreen Hill Condominiums

Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (69)
"I would love to stay here again. Decor was great, spacious, great kitchen. Wonderful property."
United States
Nergiz
The price is S$201
includes taxes & fees
23 Dec - 24 Dec
Evergreen Hill Condominiums
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

Bridgeport Waterfront Resort

Bridgeport Waterfront Resort

10/10 Excellent
"Quiet and peaceful"
Michael 1-night trip
Posted 3 days ago
Bridgeport Waterfront Resort

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.

How many holiday rentals will I find in Baileys Harbor?

Expedia has 66 holiday 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 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.