Baileys Harbor Holidays
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Top hotels in Baileys Harbor
Gordon Lodge
1420 Pine Drive Baileys Harbor WI
S$203
27 Sept - 28 Sept
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"We like everything about Gordon Lodge. The view, the grounds, our room and the breakfast."
Reviewed on 19 Sept, 2026
Beachfront Inn
8040 State Hwy 57 Baileys Harbor WI
S$221
28 Sept - 29 Sept
includes taxes & fees
9.2/10 Wonderful! (363 reviews)
"Cute, quaint motel - small private beach just steps away from rooms with fire pit, and nice patio with gas fire pit. Close to shops and restaurants. Bailey's Harbor is most definitely a slower pace than Fish Creek what is what we were looking for."
Reviewed on 15 Sept, 2026
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
Photo by Michelle M
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.
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.
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.
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.
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 harbour views and clear waters at this tranquil Lake Michigan beach retreat.
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.
What to do in Baileys Harbor
Door County’s Northern Peninsula: A Self-Guided Drive
S$25
per traveller
100% of travellers recommend
A Self-Guided Drive of Southern Door County's Natural Heritage
S$25
per traveller
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?
- 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.
- 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.
- 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.
- Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Baileys Harbour holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
