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Baileys Harbor vacation rentals

We found 738 vacation rentals — enter your dates for availability

Select from 71 houses, 17 condos, and other vacation rentals to find the perfect place for your stay in Baileys Harbor. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include cable TV and a washer and dryer. What you'll find is a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Baileys Harbor

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Image gallery for Welcome to your cozy home away from home Kookaburra Cottage at Kangaroo Lake!

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10 out of 10 rating
Exceptional
(20 reviews)

Welcome to your cozy home away from home Kookaburra Cottage at Kangaroo Lake!

Baileys Harbor, WI

8% off
Price is $263
$1,840 for 7 nights
All fees included
Welcome to your cozy home away from home Kookaburra Cottage at Kangaroo Lake!

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Find out more about Baileys Harbor

Find out more about Baileys Harbor

Why visit Baileys Harbor

  1. Outdoor Adventures: Baileys Harbor is perfect for nature lovers, offering activities like fishing, hiking, and exploring national parks.
  2. Scenic Beaches: Enjoy stunning waterfront views and relax on beautiful local beaches for a perfect day in the sun.
  3. Charming Accommodations: Choose from cozy cottages, lakeside cabins, or comfortable inns for a relaxing stay.
  4. Art and Culture: Discover local galleries and vibrant cultural experiences that showcase the area's artistic spirit.
  5. Friendly Atmosphere: Experience the warmth of the local community, making your visit feel welcoming and memorable.

Popular types of accommodation in Baileys Harbor

If you're considering a getaway to Baileys Harbor, you'll find a variety of appealing options to suit your needs. Popular accommodations include cozy cottages, inviting houses, and modern condos. Whether you prefer the charm of a Baileys Harbor cottage, the tranquility of a lakeside cabin, or the convenience of a Baileys Harbor condo, you're sure to find the perfect spot for your relaxing retreat.

  • Condos: The top choice for visitors in Baileys Harbor, offering modern amenities and convenient locations.
  • Houses: A great option for families or groups, providing spacious living and a home-like atmosphere.
  • Cottages: Quaint and charming, these rentals provide a cozy escape amidst beautiful surroundings.
  • Cabins: Ideal for nature enthusiasts, offering a rustic vibe and proximity to outdoor adventures.
  • Apartments: A practical and budget-friendly choice, perfect for couples or solo travelers.**

Top attractions in Baileys Harbor

Baileys Harbor, Wisconsin, offers a charming blend of outdoor adventures, stunning scenery, and romantic escapes. Popular attractions include national parks, beautiful beaches, and local galleries, catering to culture and nature enthusiasts alike. For those eager to explore, consider fishing charters and other engaging activities that highlight the area's natural beauty. Whether you're traveling solo or with loved ones, Baileys Harbor promises memorable experiences amidst its picturesque landscapes.

  1. Peninsula State Park: Located 8 miles from Baileys Harbor, this expansive park offers breathtaking scenery, adventure activities, and a chance to immerse yourself in nature with hiking trails and scenic vistas.
  2. Kangaroo Lake: Nestled within Baileys Harbor, this picturesque lake features romantic beach spots perfect for relaxing, swimming, and enjoying stunning outdoor views amidst tranquil surroundings.
  3. Cana Island Lighthouse: A historic gem situated in Baileys Harbor, this lighthouse invites visitors to explore its rich maritime history and enjoy cultural experiences with panoramic views of Lake Michigan.

Things to do recommended for couples

Experience romance in Baileys Harbor! Visit Stone's Throw Winery for lovely vibes, enjoy a concert at Birch Creek Music Performance Center, and have fun at Pirate's Cove Adventure Golf. Each spot offers a unique atmosphere perfect for couples looking to create unforgettable memories together.

Things to do recommended for families

Families visiting Baileys Harbor will love exploring the natural beauty at Cave Point County Park, enjoying thrilling rides at Egg Harbor Fun Park, and relaxing at Frank E. Murphy Park. These experiences offer a perfect blend of adventure and tranquility for everyone in the family.

Things to do recommended for groups

Experience the local vibe at Door County Brewing Company for some craft brews, catch a show at the Door Community Auditorium for rich culture, or enjoy a round of golf at The Orchards at Egg Harbor, all perfect activities for group travelers in Baileys Harbor.

What do I need to keep in mind when booking a vacation in Baileys Harbor

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences while searching. Here are some helpful booking tips for using Vrbo.

  • Traveling to Baileys Harbor with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Baileys Harbor with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Baileys Harbor: For many families, a vacation isn’t truly fulfilling unless their furry companion is along for the ride. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Baileys Harbor: If you're seeking vacation rentals that offer great deals for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search for an even better experience.

Where to stay in Baileys Harbor

Baileys Harbor, Wisconsin, offers an idyllic escape for outdoor enthusiasts and romantics alike. Nestled on the eastern shore, this charming town boasts friendly locals and breathtaking scenery. Explore the vibrant downtown area, relax in cozy beach houses, and embark on family-friendly excursions. With its serene atmosphere and stunning vistas, Baileys Harbor is the perfect destination for a rejuvenating vacation filled with memorable experiences.

  • Sister Bay: Located 8 miles from Baileys Harbor, Sister Bay is a charming village known for its stunning outdoor scenery and romantic ambiance. This picturesque destination is perfect for nature enthusiasts, featuring beautiful lakes and a serene beach. Visitors can enjoy various recreational activities, including golfing at local courses and exploring the nearby national state park. The vibrant waterfront is dotted with shops and eateries, making it a delightful spot for leisure and relaxation.
  • Sturgeon Bay: Situated 20 miles from Baileys Harbor, Sturgeon Bay is a hub of outdoor activities and scenic beauty. This city offers a blend of recreational areas and natural landmarks, such as the expansive national state park and pristine lakes. Travelers can indulge in golf, hiking, and fishing, or simply enjoy a leisurely day in the park. Sturgeon Bay's charming downtown area is filled with unique shops and restaurants, providing a delightful experience for visitors looking to explore the local culture.
  • Fish Creek: Just 7 miles from Baileys Harbor, Fish Creek is celebrated for its vibrant outdoor scene and artistic flair. Known for its beautiful lakes and access to the national state park, this city is ideal for those who love nature and recreation. Visitors can engage in various activities, including hiking, theater performances, and exploring local parks. The charming village atmosphere offers a mix of boutique shopping and dining options, making it a perfect destination for a romantic getaway.

Best time to go to Baileys Harbor

If you're planning a trip to Baileys Harbor, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.5°F (-5.3°C)No Rain (Dry)Mostly CloudyAverageModerately Low
February21.4°F (-5.9°C)No Rain (Dry)Mostly CloudyLowAverage
March30.0°F (-1.1°C)Light RainMostly CloudyAverageAverage
April38.1°F (3.4°C)Light RainMostly CloudyAverageAverage
May47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
June57.6°F (14.2°C)Light RainMostly SunnyHighAverage
July66.7°F (19.3°C)Light RainMostly SunnyHighModerately High
August67.6°F (19.8°C)Light RainMostly SunnyHighModerately High
September61.7°F (16.5°C)Light RainMostly SunnyAverageModerately High
October50.4°F (10.2°C)Light RainMostly SunnyAverageAverage
November39.0°F (3.9°C)Light RainMostly CloudyLowModerately Low
December29.7°F (-1.3°C)Light RainMostly CloudyLowModerately Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your full booking. Being the organizer truly has its benefits! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy and organized way to plan your travels. You can effortlessly create new trips, continue from where you last left off, or review and arrange your existing plans. Your saved or booked properties will be neatly categorized into Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Head to the tranquil city of Baileys Harbor

The lake and other outdoor surroundings create an inviting atmosphere in Baileys Harbor. This relaxing city is known for its hiking, biking and restaurants. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Baileys Harbor

Do you want to discover attractions to visit while you're in the area? Travelers enjoy Baileys Harbor for its hiking, biking and kayaking. Venture out of your vacation home and check out everything that makes Baileys Harbor a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Egg Harbor Fun Park (8.5 mi / 13.7 km)
  • Cave Point County Park (9.6 mi / 15.4 km)
  • Whitefish Dunes State Park (10.5 mi / 16.8 km)
  • Potawatomi State Park (19.8 mi / 31.8 km)
  • Stone's Throw Winery (3.4 mi / 5.4 km)
  • The Orchards at Egg Harbor (6.4 mi / 10.3 km)

Exploring the natural features in Baileys Harbor

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Baileys Harbor is a great spot to appreciate mother nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Kangaroo Lake (2.8 mi / 4.5 km)
  • Ephraim Public Beach (6.4 mi / 10.3 km)
  • Eagle Harbor (7.2 mi / 11.6 km)
  • Fish Creek Public Beach (7.2 mi / 11.7 km)
  • Egg Harbor Beach (7.9 mi / 12.7 km)
  • Waterfront Park (8.6 mi / 13.9 km)

Frequently asked questions

What is the best area to stay in Baileys Harbor when booking a vacation rental?
When planning a vacation rental in Baileys Harbor, Wisconsin, one of the best areas to consider is the waterfront district. This charming neighborhood offers stunning views of Lake Michigan, making it a picturesque spot for those who appreciate natural beauty and outdoor activities. You will find a variety of vacation rentals here, from cozy cottages to larger homes, providing ample options for families and groups.

Staying near the waterfront not only allows for easy access to scenic shorelines but also places you close to top attractions like the Baileys Harbor Ridges County Park. This park features beautiful trails and wildlife viewing opportunities, great for hiking enthusiasts and nature lovers. Additionally, the nearby Cana Island Lighthouse offers a glimpse into the area's maritime history and breathtaking panoramic views from the top.

Another appealing option is the area around Baileys Harbor's downtown, where you can enjoy a vibrant atmosphere filled with local shops, restaurants, and galleries. This location offers a more community-oriented experience, making it easy to immerse yourself in the local culture.
How much does it cost to rent a vacation home in Baileys Harbor?
Prices for vacation rentals in Baileys Harbor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Baileys Harbor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Baileys Harbor vacation house rentals?
You can find great discounts on house rentals in Baileys Harbor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Baileys Harbor?
For renting a beach house in Baileys Harbor, travelers should focus on the scenic waterfront areas along Lake Michigan. The vicinity near the Baileys Harbor State Natural Area offers vacation homes with stunning views of the water, often featuring amenities such as spacious decks, outdoor grills, and fire pits, great for evenings by the lake. Many properties here provide easy access to the beach, allowing for swimming, kayaking, and fishing right at your doorstep.

The area around the Ridges Sanctuary is also a fantastic choice, where visitors can find charming cottages located among natural landscapes. These rentals frequently come with amenities like fully equipped kitchens and cozy living spaces, ideal for families or groups looking to enjoy a peaceful retreat. The proximity to hiking trails and the sanctuary's unique ecosystems enhances the outdoor experience, with many homes offering bikes or kayaks for exploring the area.

Furthermore, Baileys Harbor is close to local attractions such as lighthouses and dining options, giving guests the opportunity to savor fresh seafood and regional cuisine.
What is the most popular type of vacation rental accomodation in Baileys Harbor?
In Baileys Harbor, vacation houses are the most popular type of rental, with about 69 available throughout the area. These homes are typically located near the stunning shores of Lake Michigan, providing easy access to the beach and scenic views. Most vacation houses come with spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying summer evenings.

In addition, there are roughly 20 cottages that offer a charming, cozy atmosphere, often located in more wooded or secluded areas, great for those seeking a peaceful retreat. For travelers looking for more compact options, about 16 condos are available, featuring modern amenities and communal facilities like pools or fitness centers. Additionally, there are several apartments and around 12 cabins, which provide a rustic experience while still being close to local attractions such as the Baileys Harbor Range Lights and the nearby nature preserves.
Are there any family house rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are numerous family-friendly vacation rentals available, with around 99 options to choose from. This charming area is known for its stunning natural scenery and proximity to the beautiful Door County coastline, making it a great destination for families. Many homes feature spacious layouts ideal for groups, complete with fully equipped kitchens that allow for convenient meal preparation. Visitors can also enjoy outdoor spaces, such as decks or patios, where children can play or the family can gather for barbecues.

The locale is close to various attractions, including the scenic Ridges Sanctuary, which offers trails for hiking and birdwatching, and the picturesque Baileys Harbor Range Lights, providing a glimpse into maritime history. Families can explore nearby parks and beaches, ensuring plenty of opportunities for outdoor activities. See all family-friendly rentals in Baileys Harbor.
Can I rent a vacation home with a pool or hot tub in Baileys Harbor?
In Baileys Harbor, travelers can find a variety of vacation homes available for rent that feature pools or hot tubs, with around 16 options to choose from. This picturesque location in Door County offers a mix of waterfront properties and cozy retreats located among the stunning natural surroundings. Many rentals come equipped with private pools or hot tubs, providing a relaxing atmosphere after a day of exploring the area.

Visitors can also expect amenities such as outdoor decks, spacious living areas, and fully equipped kitchens, making these homes ideal for families or groups looking to unwind. Find your rental in Baileys Harbor with a pool or a hot tub.
Can I find long-stay vacation rentals in Baileys Harbor?
A long-stay vacation rental in Baileys Harbor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Baileys Harbor?
In Baileys Harbor, travelers can find a variety of pet-friendly house rentals, with around 50 options available. This charming coastal town offers vacation homes that typically feature amenities such as fully equipped kitchens, outdoor spaces, and cozy living areas, making them an excellent choice for families or groups traveling with pets. Many properties also include features like fenced yards, which are great for letting dogs play safely while enjoying the fresh air.

The surrounding area is home to several pet-friendly points of interest, including the picturesque Door County Coastal Byway, which offers scenic views and walking trails. Additionally, the nearby Baileys Harbor Range Light provides a great backdrop for leisurely walks with pets. For those looking to explore, the nearby parks and beaches are welcoming to pets, allowing for plenty of outdoor activities and enjoyment of the beautiful Wisconsin scenery. See all pet-friendly rentals in Baileys Harbor.
Are there any remote work vacation rentals in Baileys Harbor?
In Baileys Harbor, there are numerous vacation rentals that cater to remote work needs, with around 103 options available. This charming town, located along the scenic Door County coastline, offers a peaceful setting ideal for productivity. Many of these properties are equipped with essential remote work amenities, such as high-speed Wi-Fi, dedicated workspace areas, and comfortable desk chairs, ensuring a conducive environment for getting work done.

Travelers can expect a variety of accommodations, ranging from cozy cottages to spacious homes, often featuring modern conveniences like fully equipped kitchens and outdoor spaces for relaxation during breaks. The picturesque surroundings provide plenty of opportunities for outdoor activities, including hiking and exploring the nearby parks, making it easy to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Baileys Harbor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Baileys Harbor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Baileys Harbor?
In Baileys Harbor, popular rental amenities typically include WiFi, kitchens, patios, coffee and tea makers, and decks or patios. These features allow travelers to stay connected, prepare their own meals, and enjoy the beautiful surroundings from outdoor spaces.
When is the best time to visit Baileys Harbor for a vacation rental?
The best time to visit Baileys Harbor for a vacation rental is during the peak summer months of June to August, with July being particularly popular. This is when the area comes alive with warm weather, superb for outdoor activities like kayaking, hiking, and exploring the stunning landscapes of Door County.

During these summer months, visitors can enjoy temperatures ranging from the mid-70s to low 80s Fahrenheit, creating a comfortable backdrop for exploring local parks and enjoying scenic views along the shoreline. The vibrant atmosphere draws many travelers looking to experience the charm of Baileys Harbor, along with its lively events and picturesque sunsets.

For those seeking a more budget-friendly option, consider planning your visit in November. This month offers a quieter experience, allowing you to appreciate the serene beauty of the fall season without the hustle and bustle of peak tourist traffic.
How early should I book a Baileys Harbor vacation rental?
Book your Baileys Harbor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Baileys Harbor?
In Baileys Harbor, visitors can enjoy a variety of attractions that highlight the area's natural beauty and charm. The Baileys Harbor Range Lights, a historical landmark, offer a glimpse into the region's maritime history and provide stunning views of the harbor. Nearby, the beautiful Door County Coastal Byway presents scenic views and access to picturesque beaches, superb for a leisurely drive or a day of exploration.

The Ridges Sanctuary, located just outside of town, features unique ecosystems and well-maintained hiking trails, making it a great spot for nature lovers. Additionally, vacation rentals in the area often provide easy access to local art galleries, shops, and restaurants that showcase the region's culinary delights.
Can I change or cancel my Baileys Harbor home rental booking on Vrbo?
To find Baileys Harbor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Baileys Harbor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.