Baileys Harbor Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric & Kristy's Adventures

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Baileys Harbor Vacation Packages

Baileys Harbor Hotel Deals

Gordon Lodge
Gordon Lodge
4 out of 5
1420 Pine Drive, Baileys Harbor, WI
The price is ₩271,515 per night from Jul 13 to Jul 14
₩271,515
₩334,197 total
Jul 13 - Jul 14
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"So beautiful"

Reviewed on Jul 2, 2025

Gordon Lodge
Beachfront Inn
Beachfront Inn
2 out of 5
8040 State Hwy 57, Baileys Harbor, WI
The price is ₩285,553 per night from Jul 14 to Jul 15
₩285,553
₩324,107 total
Jul 14 - Jul 15
includes taxes & fees
9.4/10 Exceptional! (277 reviews)
"This property was wonderful. It was clean and inviting and the staff were great. I will definitely go back."

Reviewed on Jun 30, 2025

Beachfront Inn
Scandinavian Lodge
Scandinavian Lodge
3.5 out of 5
10506 State HWY 57, Sister Bay, WI
9.2/10 Wonderful! (1,432 reviews)
"Easy reservation and check in. Condo very clean and well furnished. Location is excellent- close to shopping, dining and local attractions. Only thing we didn’t like was the multiple doors by bathroom and bedroom. Always hitting each other due to hall and bedroom access."

Reviewed on Jul 6, 2025

Get rates
Scandinavian Lodge
See all 1,160 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.

Discover the most popular places to visit in Baileys Harbor

What A beautiful day to go see Lake Michigan from the top of the lighthouse. #Blue Travel Photo Contest

Cana Island Lighthouse

4.5/5(186 reviews)

You can find out about the history of Baileys Harbor with a trip to Cana Island Lighthouse. Amble around this relaxing area's waterfront, or seek out the hiking trails.

Cana Island Lighthouse

Anclam Beach Park

5/5(1 review)

Why not spend a carefree afternoon at Anclam Beach Park during your travels in Baileys Harbor? Amble around this relaxing area's lakeside and enjoy its top-notch restaurants.

Anclam Beach Park

Frequently asked questions

How much does a Baileys Harbor vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Baileys Harbor costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Baileys Harbor?
The off-season is the best time to head to Baileys Harbor if you're trying to save. Another tip for scoring cheap Baileys Harbor vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Baileys Harbor?
The ideal duration for your Baileys Harbor vacation 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 vacation package to Baileys Harbor?
Popular for its family-friendly attractions, watersports and views, a Baileys Harbor vacation 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 Harbor package deals?
Use Expedia's filter tool to help you find some of the best Baileys Harbor 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 Harbor 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 vacation package well in advance.
Is it cheaper to book a Baileys Harbor vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations separately. Better still, you can tailor your Baileys Harbor 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 vacation package to Baileys Harbor?
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 Harbor trip.
How to plan a trip to Baileys Harbor?

  1. Choose when to travel: Check your calendar and pack your bags. Your favorite season and the activities on offer will also help you decide when to escape to Baileys Harbor.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will likely be the largest expense during your trip to Baileys Harbor.
  3. Decide how long to go away for: Now that you're up to speed on Baileys Harbor, 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 accommodations: After you've nailed down your dates and duration, lock in the right Baileys Harbor vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.