Baileys Harbor Vacations from $622

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Photo by Eric & Kristy's Adventures

Your Baileys Harbor Vacation

The lively city of Baileys Harbor is calling your name. Discover all its secrets with a Baileys Harbor vacation package that's custom made for you. Want to venture out and explore? Door County Brewing Company, Kangaroo Lake and Cana Island Lighthouse are three of the most popular places to visit during your trip to Baileys Harbor. Your ideal Baileys Harbor vacation is a couple of clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored just for you.

The Latest Baileys Harbor vacation packages

Price found within the past 48 hours. Click for updated prices.
Tundra Lodge

Tundra Lodge

3.5 out of 5
Price was $832, price is now $622 per person
$622
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Green Bay (GRB)
7.4/10 Good! (1,333 reviews)
It’s okay boring though

Reviewed on Aug 22, 2025

The Goat House Waterfront Hottub 3 Acres

The Goat House Waterfront Hottub 3 Acres

2 out of 5
Save 100% on your flight
Price was $4,127, price is now $3,063 per person
$3,063
per person
Oct 30 - Nov 3
found 12 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Green Bay (GRB)
No reviews
The Waterfront - Waterslide Game Room Sleeps 26

The Waterfront - Waterslide Game Room Sleeps 26

2 out of 5
Save 100% on your flight
Price was $2,511, price is now $1,955 per person
$1,955
per person
Oct 30 - Nov 3
found 12 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Green Bay (GRB)
No reviews
Riverfront Kayaks Bay Access Sleeps 15

Riverfront Kayaks Bay Access Sleeps 15

2 out of 5
Price was $1,841, price is now $1,473 per person
$1,473
per person
Oct 30 - Nov 3
found 12 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Green Bay (GRB)
No reviews
DoubleTree by Hilton Neenah

DoubleTree by Hilton Neenah

4 out of 5
Price was $756, price is now $659 per person
$659
per person
Nov 8 - Nov 11
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Green Bay (GRB)
8.6/10 Excellent! (968 reviews)
This place is how all motels should be. Everything was perfect.

Reviewed on Aug 24, 2025

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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 family-friendly area's waterfront, or seek out the hiking trails.

Cana Island Lighthouse

Door County Brewing Company

4.5/5(14 reviews)

Enjoy a trip to Door County Brewing Company and popular activities like hiking in Baileys Harbor. Amble around this romantic area's waterfront and enjoy its seafood restaurants.

Door County Brewing Company

Kangaroo Lake

4.5/5(32 reviews)

Commune with nature and explore the great outdoors at Kangaroo Lake during your travels in Baileys Harbor. Stroll along the lakeside in this relaxing area, or check out its top-notch restaurants.

Kangaroo Lake

What to do in Baileys Harbor

Baileys Harbor Lighthouses Segway Tour

Baileys Harbor Lighthouses Segway Tour

$101
per adult
Baileys Harbor Lighthouses Segway Tour
Baileys Harbor Lighthouse Segway/Hike Tour with Private Tour Opt

Baileys Harbor Lighthouse Segway/Hike Tour with Private Tour Opt

$112
per adult
Baileys Harbor Lighthouse Segway/Hike Tour with Private Tour Opt
Fish Creek E-Scooter Guided Nature Glide w/ Private Tour Option

Fish Creek E-Scooter Guided Nature Glide w/ Private Tour Option

$57
per adult
Fish Creek E-Scooter Guided Nature Glide w/ Private Tour Option
See all activities in Baileys Harbor

Baileys Harbor Hotel Deals

Gordon Lodge

Gordon Lodge

4 out of 5
1420 Pine Drive, Baileys Harbor, WI
$153 nightly
The price is $171 total per night from Sep 8 to Sep 9
$171 total
Sep 8 - Sep 9
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
"Would love to spend more time there"

Reviewed on Aug 22, 2025

Gordon Lodge
Beachfront Inn

Beachfront Inn

2 out of 5
8040 State Hwy 57, Baileys Harbor, WI
$149 nightly
The price is $169 total per night from Sep 8 to Sep 9
$169 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (290 reviews)
Beachfront Resort.
"Beachfront. Hidden gem. Had view of Lake Michigan. Dog friendly"

Reviewed on Aug 20, 2025

Beachfront Inn
Maxwelton Braes Lodge and Golf Course

Maxwelton Braes Lodge and Golf Course

2 out of 5
7670 Highway 57, Baileys Harbor, WI
8.2/10 Very Good! (164 reviews)
"New owners taking pride of ownership in a true vintage property. While keeping some of the original and distinctive parts of the property, new updates have been made to create a warm, welcoming, and romantic destination. Restaurant owner is very hands on and consistently providing a great menu served ..."

Reviewed on Aug 13, 2025

Get rates
Maxwelton Braes Lodge and Golf Course
See all 1,153 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.

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Frequently asked questions

How much does a Baileys Harbor vacation package cost?
You can snap up a vacation package to this top destination from $622 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?
You can generally find reduced prices and better availability in November, December and January. Browse our cheap Baileys Harbor vacation packages and you could get some excellent off-season deals.
How many days is enough for Baileys Harbor?
With a well-planned itinerary, you can easily tick off the most popular Baileys Harbor attractions in a few days. But if you prefer to venture off the beaten track or take day trips, think about booking your Baileys Harbor vacation for longer.
Is it worth booking a vacation package to Baileys Harbor?
Whether you want to explore attractions such as Kangaroo Lake and Ridges Sanctuary on your Baileys Harbor vacation, or coming for its excellent family-friendly attractions, watersports and views, there's something for everyone here. With so many things to do, you'll soon learn why so many visitors think Baileys Harbor is a good vacation destination.
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 your dates: What you want to do in Baileys Harbor and your favorite season can help you decide when to travel.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may arise during your trip to Baileys Harbor.
  3. Organize your Baileys Harbor escape with our trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Baileys Harbor together.
  4. Set the duration of your trip: Start by listing all the activities and attractions you want to get to in Baileys Harbor. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your accommodations and airfare: Once you've nailed down your dates and duration, book the perfect Baileys Harbor vacation package for you.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to do and see. Explore some of the incredible things to do in Baileys Harbor and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Baileys Harbor vacation packages?
Your Baileys Harbor trip is meant to be an escape from your daily routine, not a reason for money worries. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.