Baileys Harbor Vacation Packages

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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.

Top Baileys Harbor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Nuks Executive Suites

Nuks Executive Suites

CA $1,150
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Green Bay (GRB)
9.2/10 Wonderful! (1,026 reviews)
Everything at Nuk’s was better than advertised. We had an exceptional experience.

Reviewed on Sep 6, 2026

Full Remodel Steps to Lambeau Titletown Resch

Full Remodel Steps to Lambeau Titletown Resch

CA $7,181
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Green Bay (GRB)
No reviews
House w Finished Garage Walk to Lambeau Bars Resch

House w Finished Garage Walk to Lambeau Bars Resch

Lombardi
CA $5,619
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Green Bay (GRB)
No reviews

Ready to book your vacation to Baileys Harbor?

Choose your dates

Baileys Harbor Hotel Deals

Gordon Lodge

Gordon Lodge

1420 Pine Drive Baileys Harbor WI
CA $131
CA $180 total
Sep 7 - Sep 8
includes taxes & fees
Gordon Lodge
Beachfront Inn

Beachfront Inn

8040 State Hwy 57 Baileys Harbor WI
CA $212
CA $240 total
Sep 28 - Sep 29
includes taxes & fees
9.2/10 Wonderful! (361 reviews)
"Very nice place to stay. We even checked in after hours and staff was very helpful. Would highly recommend to anyone. Beautiful spot on the water!"

Reviewed on Sep 3, 2026

Beachfront Inn
Lakefront Cottage Retreat w/ Private Dock, Paddle Boards, Fire Pit, Sunset Views

Lakefront Cottage Retreat w/ Private Dock, Paddle Boards, Fire Pit, Sunset Views

Baileys Harbor WI
CA $315
CA $678 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (15 reviews)
"Super cute and cozy cabin with a beautiful lake view. Would definitely rent again!"

Reviewed on Aug 30, 2026

Lakefront Cottage Retreat w/ Private Dock, Paddle Boards, Fire Pit, Sunset Views
See all 1,228 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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Stay near popular Baileys Harbor attractions

A spiral staircase with a geometric metal railing.
Photo by Melissa Beaudry Palmer

Cana Island Lighthouse

9.0/10 (420 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.
See properties
A group of people sitting around a wooden table in a room with a window and a hanging light fixture.
Photo by Eric & Kristy's Adventures

Door County Brewing Company

9.0/10 (62 reviews)
Enjoy a trip to Door County Brewing Company and popular activities like hiking in Baileys Harbor. Amble around this family-friendly area's waterfront and enjoy its seafood restaurants.
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An aerial view of a large lake with a small island and a residential area along the shore.

Kangaroo Lake

9.2/10 (68 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.
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A white church with a red roof and a green door, surrounded by trees.

Ridges Sanctuary

9.2/10 (42 reviews)
Explore the lovely green spaces of Ridges Sanctuary and enjoy the hiking trails in Baileys Harbor. Stroll along the lakeside in this relaxing area, or check out its seafood restaurants.
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Baileys Harbor Ridges Park

9.2/10 (89 reviews)
Explore the lovely green spaces of Baileys Harbor Ridges Park and enjoy the hiking trails in Baileys Harbor. Amble around this romantic area's waterfront and enjoy its seafood restaurants.
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Stone's Throw Winery

8.0/10 (100 reviews)
You can enjoy a tasting or tour at Stone's Throw Winery during your travels to Baileys Harbor. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.
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Door Shakespeare

6.6/10 (4 reviews)
You can get tickets for a performance at Door Shakespeare on your trip to Baileys Harbor. Stroll along the riverfront in this romantic area, or check out its seafood restaurants.
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Anclam Beach Park

9.0/10 (11 reviews)
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.
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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

CA $28
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

CA $28
per traveller
A Self-Guided Drive of Southern Door County's Natural Heritage
See all activities in Baileys Harbor

Frequently asked questions

How much does a Baileys Harbour vacation package cost?
You'll find cheap prices from CA $1,150 on Expedia for your Baileys Harbour escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Baileys Harbour costs.
What are the cheapest months to go to Baileys Harbour?
Plan your trip for the off-peak season and you're likely to score cheap Baileys Harbour vacation packages. Bear in mind that school vacation periods and major events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Baileys Harbour?
With a well-planned schedule, you can easily hit the most popular Baileys Harbour attractions in a few days. But if you'd like to explore off the beaten track or take day trips, consider booking your Baileys Harbour vacation for longer.
Is it worth booking a vacation package to Baileys Harbour?
Baileys Harbour has all the ingredients you need for an amazing trip — family-friendly attractions, watersports and views are just the start. Whether you want to visit attractions such as Kangaroo Lake and Door Shakespeare, or venture off the beaten track, you'll find plenty to see and do on your Baileys Harbour vacation.
How to find the best Baileys Harbour package deals?
Start your search for a Baileys Harbour package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Baileys Harbour package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Baileys Harbour escape off to a flying start.
Is it cheaper to book a Baileys Harbour vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Baileys Harbour vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Baileys Harbour?
If you're planning a spontaneous Baileys Harbour trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Baileys Harbour?
  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Baileys Harbour.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may come up during your trip to Baileys Harbour.
  3. Work out your trip length: Consider how much time you want to spend discovering Baileys Harbour. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Baileys Harbour vacation package for you.

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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.