Baileys Harbor vacation rentals

We found 731 vacation rentals — enter your dates for availability

Select from 67 houses, 20 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

Showing deals for:Mar 6 - Mar 13

Image gallery for The Lookout, near Sister Bay with Starlink internet

Welcome to the lookout!
10 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

The Lookout, near Sister Bay with Starlink internet

Ellison Bay, WI

8% off
Price is $728
$5,099 for 7 nights
All fees included
The Lookout, near Sister Bay with Starlink internet

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Find out more about Baileys Harbor

Why visit Baileys Harbor

  • Outdoor Activities: Enjoy hiking, biking, and water sports in the stunning natural surroundings of Baileys Harbor.
  • Scenic Beaches: Relax on beautiful beaches with tranquil waters, perfect for sunbathing and swimming.
  • Historic Lighthouses: Visit iconic lighthouses that showcase the area's maritime history and offer breathtaking views.
  • Charming Downtown: Explore local shops and art galleries in a friendly atmosphere filled with welcoming locals.
  • Cozy Accommodations: Choose from a variety of charming vacation rentals, including cottages and condos, for a perfect stay.

Popular types of accommodation in Baileys Harbor

If you're looking for the perfect getaway, Baileys Harbor offers a range of charming vacation rentals to suit your needs. Discover cozy cottages, spacious houses, and modern condos that provide the comfort and amenities you desire. Whether you’re seeking a peaceful retreat or a fun-filled holiday, our selection of house rentals and holiday cottages ensures you'll find the ideal spot to relax and enjoy the beauty of Baileys Harbor.

  • Houses: The top choice for travelers, these spacious homes offer privacy and comfort, ideal for families or groups.
  • Condos: A popular option, condos provide a blend of hotel amenities and home-like features, perfect for a convenient stay.
  • Cottages: Quaint and cozy, cottages are a favorite for those seeking a charming retreat close to nature.
  • Cabins: Rustic and inviting, cabins offer a unique experience for outdoor enthusiasts looking to unwind.
  • Apartments: A practical choice for shorter stays, apartments deliver essential comforts with a local vibe.**

Top attractions in and around Baileys Harbor

Baileys Harbor, Wisconsin, is a picturesque destination perfect for outdoor enthusiasts and romantic getaways. Visitors can explore beautiful beaches, art galleries, and historic lighthouses, offering a blend of culture and natural beauty. Whether you're seeking relaxation by the shore or engaging in outdoor activities, Baileys Harbor provides a delightful experience for all types of travelers looking to embrace the great outdoors.

  • Cana Island Lighthouse: Experience the charm of this historic lighthouse, which offers a glimpse into maritime history and stunning views of Lake Michigan. The cultural vibes and picturesque surroundings make it a must-visit spot.
  • Kangaroo Lake: Enjoy romantic moments at Kangaroo Lake, where you can relax on the beach, take in scenic views, and engage in various outdoor activities. It's perfect for a peaceful day by the water.
  • Fish Creek Public Beach: Located 7 miles from Baileys Harbor, this beach is ideal for sunbathing and swimming. With its vibrant beach vibes, it's a popular spot for families and beach lovers alike.

Things to do recommended for couples

For a romantic getaway in Baileys Harbor, visit Stone's Throw Winery for a cozy atmosphere, enjoy a concert at Birch Creek Music Performance Center, or savor fine wines at Harbor Ridge Winery. Each offers a unique blend of romance and entertainment, perfect for couples seeking memorable experiences.

Things to do recommended for families

Your family will love exploring the Ridges Sanctuary in Baileys Harbor, where you can enjoy nature and relax. For some adventure, head to Egg Harbor Fun Park, just 8 miles away, for thrilling go-karting fun that will delight kids and adults alike.

Things to do recommended for groups

Experience the local charm at Door County Brewing Company for a taste of craft beer, enjoy a performance at Peninsula Players Theatre, and catch a movie under the stars at The Skyway Drive-In Theatre. These activities are perfect for creating lasting memories with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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 when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Baileys Harbor with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Baileys Harbor with young kids: Traveling with little ones can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Baileys Harbor: For many families, a vacation isn't truly fulfilling without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Baileys Harbor: If you’re in search of vacation rentals that offer great deals for stays of a month or more, 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Baileys Harbor

Baileys Harbor, Wisconsin, is a hidden gem perfect for outdoor enthusiasts and those seeking a romantic getaway. Explore the charming downtown area, where friendly locals welcome you with open arms. The breathtaking scenery of Door County surrounds you, offering relaxing excursions and picturesque views. Whether you're enjoying a peaceful day by the water or indulging in local cuisine, Baileys Harbor promises an unforgettable vacation experience filled with tranquility and natural beauty.

  • Ephraim: Ephraim is a charming city located a mere 7 miles from Baileys Harbor, offering breathtaking scenery and a romantic atmosphere. This picturesque destination is perfect for outdoor enthusiasts, featuring a range of recreational areas and a popular golf course. Visitors can explore the nearby national state park, relax on beautiful beaches, or enjoy serene views of the lake. Ephraim's quaint shops and eateries add to the overall travel experience, making it an ideal spot for couples and families alike.
  • Jacksonport: Just 7 miles from Baileys Harbor, Jacksonport is a delightful village that beckons travelers with its stunning natural beauty and outdoor activities. Known for its scenic trails and recreational areas, visitors can immerse themselves in the peaceful environment while hiking or biking. Jacksonport is also home to a lovely park and provides convenient access to the nearby national state park and lake. The village's laid-back charm and picturesque landscapes make it a perfect getaway for those seeking romance and adventure.
  • North Bay: Nestled in the vicinity of Baileys Harbor, North Bay is a quaint village that invites travelers to experience its outdoor charm and scenic beauty. With ample recreational areas and golf opportunities, visitors can indulge in a variety of activities while soaking in the stunning views of the lake and beach. North Bay's proximity to the national state park provides easy access to hiking trails and wildlife viewing, making it a fantastic destination for nature lovers and romantics alike. Enjoy the peaceful ambiance and create lasting memories in this idyllic setting.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.5°F (-5.3°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
February21.4°F (-5.9°C)No Rain (Dry)Mostly CloudyLowSlightly Low
March30.0°F (-1.1°C)Light RainMostly CloudyAverageSlightly Low
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 SunnyHighSlightly High
July66.7°F (19.3°C)Light RainMostly SunnyHighSlightly High
August67.6°F (19.8°C)Light RainMostly SunnyHighSlightly High
September61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
October50.4°F (10.2°C)Light RainMostly SunnyAverageAverage
November39.0°F (3.9°C)Light RainMostly CloudyLowAverage
December29.7°F (-1.3°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is simple

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

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the organizer truly has its rewards. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and begin earning.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up where you left off, and manage your travel arrangements. You can easily access the properties you've saved or booked by checking the Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Peninsula State Park Golf Course (6.7 mi / 10.8 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)
  • Egg Harbor Fun Park (8.5 mi / 13.7 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)
  • Fish Creek Public Beach (7.2 mi / 11.7 km)
  • Egg Harbor Beach (7.9 mi / 12.7 km)
  • Nicolet Bay Beach (8.5 mi / 13.7 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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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