Baileys Harbor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Baileys Harbor

Gordon Lodge

Gordon Lodge

4 out of 5
1420 Pine Drive Baileys Harbor WI
The price is 7.780.313 ₫ per night from 11 Aug to 12 Aug
7.780.313 ₫
9.407.063 ₫ total
11 Aug - 12 Aug
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"We loved the charm of our cabin. It was clean, comfortable and the view was amazing! The entire property was top notch!"

Reviewed on 14 Jul 2026

Gordon Lodge
Beachfront Inn

Beachfront Inn

2 out of 5
8040 State Hwy 57 Baileys Harbor WI
The price is 5.806.086 ₫ per night from 29 Jul to 30 Jul
5.806.086 ₫
6.590.210 ₫ total
29 Jul - 30 Jul
includes taxes & fees
9.4/10 Exceptional! (349 reviews)
"Great location, friendly staff!"

Reviewed on 14 Jul 2026

Beachfront Inn
Best Western Maritime Inn

Best Western Maritime Inn

2.5 out of 5
1001 N 14th Avenue Sturgeon Bay WI
The price is 3.937.987 ₫ per night from 12 Aug to 13 Aug
3.937.987 ₫
4.489.305 ₫ total
12 Aug - 13 Aug
includes taxes & fees
8/10 Very good! (1,001 reviews)
"Would never do that again."

Reviewed on 15 Jul 2026

Best Western Maritime Inn
See all 1,224 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 spiral staircase with a geometric metal railing.
Photo by Melissa Beaudry Palmer
Open Photo by Melissa Beaudry Palmer

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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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.

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