Baileys Harbor Vacations from $689
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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.
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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.
Kangaroo Lake
9.2/10 (68 reviews)
Kangaroo Lake's pristine marshes and forests shelter the rare Hine's emerald dragonfly in a tranquil setting. Paddle through calm waters or hike scenic trails to observe diverse bird species in this natural sanctuary.
Photo by Eric & Kristy's Adventures
Door County Brewing Company
9.0/10 (62 reviews)
This lively brewery combines Door County's heritage with handcrafted beers and a vibrant music scene. Sample from 14 taps in the spacious taproom or relax in the outdoor beer garden while enjoying live performances.
Ridges Sanctuary
9.2/10 (42 reviews)
Wisconsin's first land trust protects a rare ridge-swale ecosystem with 500+ plant species and 25 native orchids. Explore boardwalks through diverse landscapes while searching for the endangered Hine's Emerald dragonfly.
Baileys Harbor Ridges Park
9.2/10 (89 reviews)
This serene Lake Michigan beach park features unique ridge and swale topography. Explore its diverse ecosystem with rare plants and endangered Hine's Emerald dragonfly while enjoying shallow swimming waters.
Stone's Throw Winery
8.0/10 (100 reviews)
Experience Door County's wine culture in this boutique winery using premium California grapes. Relax in the Tuscan-inspired tapas bar or challenge friends to bocce ball in the scenic gardens.
Door Shakespeare
6.6/10 (4 reviews)
Experience Shakespeare under a magnificent maple tree with Lake Michigan as your backdrop. Bring a blanket for comfort during the intimate outdoor performances in the Garden at Björklunden.
Anclam Beach Park
9.0/10 (11 reviews)
Stroll along the historic jetty that once served as a shipping pier for timber in the 1800s. Enjoy panoramic harbor views and clear waters at this tranquil Lake Michigan beach retreat.
What to do in Baileys Harbor
Door County’s Northern Peninsula: A Self-Guided Drive
$20
per traveler
100% of travellers recommend
A Self-Guided Drive of Southern Door County's Natural Heritage
$20
per traveler
Baileys Harbor Hotel Deals
Gordon Lodge
1420 Pine Drive Baileys Harbor WI
$263 nightly
$298 total
Aug 23 - Aug 24
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
"Really amazing and relaxing stay as always!"
Reviewed on Aug 19, 2026
Beachfront Inn
8040 State Hwy 57 Baileys Harbor WI
$175 nightly
$199 total
Sep 16 - Sep 17
Total with taxes and fees
Chalet Cabin: Sunset Shores Kangaroo Lakefront
Baileys Harbor WI
5/10 (2 reviews)
"The front screen door does not close. The back living room blinds do not close all the way. The mattress is poor due to foam topper. There was no toilet paper in the cabin except an almost depleted roll.This cabin would be better if it were maintained properly. As it is I give it a poor rating."
Reviewed on Jun 7, 2025
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.
Find the Best Baileys Harbor Vacation Packages
Baileys Harbor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 260 |
Max Temp Winter | 25ºF |
Max Temp Summer | 65ºF |
Top Sights | Peninsula State Park, Egg Harbor Beach and Whitefish Dunes State Park |
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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 $689 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?
- Choose your dates: What you want to do in Baileys Harbor and your favorite season can help you decide when to travel.
- 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.
- 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.
- 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.
- Combine your accommodations and airfare: Once you've nailed down your dates and duration, book the perfect Baileys Harbor vacation package for you.
- 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
