Baileys Harbor Holidays

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Top hotels in Baileys Harbor

Gordon Lodge

Gordon Lodge

4 out of 5
1420 Pine Drive Baileys Harbor WI
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Gordon Lodge
Beachfront Inn

Beachfront Inn

2 out of 5
8040 State Hwy 57 Baileys Harbor WI
The price is S$174 per night from 8 Nov to 9 Nov
S$174
8 Nov - 9 Nov
includes taxes & fees
9.2/10 Wonderful! (385 reviews)
"Pet friendly, very clean, friendly staff and convenient location!"

Reviewed on 1 Nov, 2026

Beachfront Inn
Scandinavian Lodge

Scandinavian Lodge

3.5 out of 5
10506 State HWY 57 Sister Bay WI
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Scandinavian Lodge
See all 1,211 properties in Baileys Harbor
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.

Stay near popular Baileys Harbor attractions

A lighthouse with a white tower and a dark top, surrounded by trees.
Photo by Michelle M
Open Photo by Michelle M

Cana Island Lighthouse

9.0/10 (420 reviews)
This 1870 maritime beacon stands tall on Lake Michigan, guiding ships for over 150 years. Climb 97 spiral steps to the gallery deck for breathtaking panoramic views of Door County's rugged shoreline.
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What to do in Baileys Harbor

Door County’s Northern Peninsula: A Self-Guided Drive

Door County’s Northern Peninsula: A Self-Guided Drive

S$27
per traveller
100% of travellers recommend
Door County’s Northern Peninsula: A Self-Guided Drive
A Self-Guided Drive of Southern Door County's Natural Heritage

A Self-Guided Drive of Southern Door County's Natural Heritage

S$26
per traveller
A Self-Guided Drive of Southern Door County's Natural Heritage
Peninsula State Park Views Segway Tour w/ Private Tour Option

Peninsula State Park Segway Tour – Scenic Door County Views

S$129
per adult
100% of travellers recommend
Peninsula State Park Segway Tour – Scenic Door County Views
See all activities in Baileys Harbor

Frequently asked questions

How much does a Baileys Harbour holiday package cost?
You can snap up a holiday package to this top destination on Expedia. However, how much your holiday to Baileys Harbour costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Baileys Harbour?
The off-season is the best time to head to Baileys Harbour if you're trying to save. Another tip for scoring cheap Baileys Harbour holiday packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Baileys Harbour?
The ideal duration for your Baileys Harbour holiday depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to visit all the main attractions and discover some hidden spots along the way.
Is it worth booking a holiday package to Baileys Harbour?
Popular for its family-friendly attractions, watersports and views, a Baileys Harbour holiday is a hit with all kinds of visitors. Be sure to check out top sights like Kangaroo Lake and Door Shakespeare, and consider renting a set of wheels for day trips to explore even more.
How to find the best Baileys Harbour package deals?
Use Expedia's filter tool to help you find some of the best Baileys Harbour package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Baileys Harbour package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Baileys Harbour holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and accommodation separately. Better still, you can tailor your Baileys Harbour trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Baileys Harbour?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Baileys Harbour trip.
How to plan a trip to Baileys Harbour?

  1. Choose when to travel: Check your calendar and pack your bags. Your favourite season and the activities on offer will also help you decide when to escape to Baileys Harbour.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodation will likely be the largest expense during your trip to Baileys Harbour.
  3. Decide how long to go away for: Now that you're up to speed on Baileys Harbour, you can work out the ideal length of your break. Put together a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Baileys Harbour holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.