Baileys Harbor vacation rentals

We found 734 vacation rentals — enter your dates for availability

Select from 67 houses, 15 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:May 22 - May 29

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

8% off
Price is $733
$5,134 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:

  • Stone's Throw Winery (3.4 mi / 5.4 km)
  • 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)
  • Harbor Ridge Winery (7.9 mi / 12.7 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)
  • 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)
  • Nicolet Bay Beach (8.5 mi / 13.7 km)

Frequently asked questions

What is the best area to stay in Baileys Harbor, Wisconsin, United States of America when booking a vacation rental?
When booking a vacation rental in Baileys Harbor, one of the best areas to consider is the waterfront neighborhood. This charming location offers stunning views of Lake Michigan and easy access to beautiful beaches. Staying here not only provides a serene atmosphere but also places you near top attractions like the Baileys Harbor Range Lights, which are a picturesque sight especially at sunset, and the scenic Ridges Sanctuary, known for its diverse wildlife and hiking trails.

Another great option is the area around downtown Baileys Harbor, where you can find a variety of cozy vacation homes and cottages. This neighborhood is close to local shops, restaurants, and the lively option of the local community. You'll also be near the iconic Baileys Harbor Marina, great for those interested in boating or fishing.
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 explore the areas along the scenic shores of Lake Michigan, particularly near the Baileys Harbor Town Park and the nearby Ridges Sanctuary. This region is known for its serene beaches and breathtaking natural beauty, making it ideal for vacation rentals. Many properties in this vicinity offer amenities such as private decks or patios with views of the lake, outdoor grills for summer cookouts, and access to sandy beaches great for swimming or sunbathing.

Additionally, the properties often include fully equipped kitchens, allowing guests to prepare their own meals after a day of exploring. The town park provides not only beach access but also picnic areas and walking trails, enhancing the outdoor experience. Nearby, the Ridges Sanctuary presents a unique opportunity to enjoy hiking trails through diverse ecosystems, with some rentals located conveniently close to these nature paths.

In Baileys Harbor, visitors can also find charming cottages and larger homes that cater to families or groups, many of which feature cozy living areas with fireplaces, great for relaxing evenings after a day of beach activities.
What is the most popular type of vacation rental accomodation in Baileys Harbor?
In Baileys Harbor, vacation houses are the most popular type of accommodation, with about 64 available throughout the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many houses also feature outdoor spaces such as decks or patios, allowing guests to enjoy the scenic surroundings. Additionally, there are around 19 cottages, which provide a cozy atmosphere and often come with unique character, great for a more intimate getaway. Condos, numbering around 15, offer modern amenities and convenient locations, while about 11 cabins provide a rustic charm for those looking to connect with nature.
Are there any family house rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are numerous family-friendly house rentals available—approximately 95 in the area. This charming locale is situated near the stunning shores of Lake Michigan, providing families with ample opportunities for outdoor activities such as swimming, fishing, and hiking. Many of the properties feature spacious living areas, fully equipped kitchens ideal for family meals, and outdoor patios or decks great for enjoying the scenic surroundings.

Visitors can explore nearby attractions like the Door County Land Trust and the beautiful Ridges Sanctuary, which offer educational nature trails and opportunities for wildlife watching. Additionally, local eateries serve delicious fare, making it easy for families to experience the area's culinary delights.
Can I rent a vacation home with a pool or hot tub in Baileys Harbor?
In Baileys Harbor, there are about 15 vacation homes available for rent that feature pools or hot tubs. This charming town, located along the scenic Door County coastline, offers a variety of accommodations that cater to those looking to relax and enjoy the outdoors. Many of these properties are equipped with private pools and hot tubs, superb for unwinding after a day of exploring the area's natural beauty.

Travelers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making these rentals ideal for families or groups. Some homes may also include features like outdoor grills, fire pits, and easy access to nearby parks and beaches, enhancing the overall vacation experience.
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, there are numerous pet-friendly house rentals available, providing travelers with a great option for a vacation with their furry companions. Many of these rentals come equipped with amenities such as fully stocked kitchens, outdoor spaces for pets to roam, and cozy living areas, ideal for families or groups.

The area is known for its stunning natural beauty, with close proximity to places like the Baileys Harbor Ridges Park and the scenic shoreline along Lake Michigan, which offer plenty of opportunities for outdoor activities with pets, including hiking and enjoying the beautiful views. Additionally, there are pet-friendly parks and trails nearby that make it easy to explore the surroundings with your dog.
Are there any remote work vacation rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are numerous vacation rentals suitable for remote work, with around 100 options available. This charming town, situated on the Door County peninsula, offers a tranquil setting great for those looking to balance work and leisure. Many properties in the area provide essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable seating, ensuring a productive environment while enjoying the scenic beauty of the surroundings.

Travelers can expect accommodations that feature spacious living areas, fully equipped kitchens, and outdoor spaces for relaxation. The proximity to local attractions, including the stunning shores of Lake Michigan and nearby parks, makes it easy to take breaks and enjoy nature. 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 vacation rental amenities cater to travelers seeking comfort and convenience. Most rentals feature well-equipped kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining. Many properties also include decks or patios, providing outdoor spaces to relax and take in the scenic beauty of the area. Cozy fireplaces are common, great for warming up after a day of exploring. Onsite parking is typically available, making it easy for guests to travel around the charming town and nearby attractions. Additionally, coffee and tea makers are standard in many rentals, ensuring that guests can start their mornings with a warm beverage.
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 summer months, primarily from June to August. This peak season draws travelers seeking to enjoy the picturesque beauty of Door County and partake in its vibrant outdoor activities. With July being the most popular month, visitors can relish warm temperatures, typically ranging from the mid-60s to mid-80s Fahrenheit, great for exploring the area's stunning landscapes, quaint shops, and local eateries.

During this time, outdoor enthusiasts can indulge in kayaking, hiking, and biking along scenic trails, all while soaking in the breathtaking views of Lake Michigan. The charming atmosphere of Baileys Harbor is further enhanced by various local festivals and events, creating a lively and welcoming environment for tourists.

For those looking for a more budget-friendly option, consider visiting in November. While this month falls outside the high tourist season, it offers a unique opportunity to experience the tranquility of Baileys Harbor as the landscape transitions into a serene winter wonderland. Enjoy peaceful walks along the shore and witness the beauty of autumn's last colors, all while enjoying lower rental rates.

Ultimately, your ideal time to visit Baileys Harbor will depend on your preferences for lively summer activities or the calm and beauty of the off-season.
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, Wisconsin, United States of America?
In Baileys Harbor, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. One of the main draws is the Baileys Harbor Range Lights, a historic pair of lighthouses that offer picturesque views and a glimpse into the maritime history of the region. Nearby, the Ridges Sanctuary is a unique natural area featuring diverse ecosystems and hiking trails, great for nature enthusiasts and bird watchers alike.

For those interested in local art and culture, the Baileys Harbor Art Gallery showcases works from local artists and often hosts events. The charming downtown area is filled with quaint shops and restaurants offering fresh seafood and local flavors, providing a delightful experience for visitors.
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.

Frequently asked questions

Can I find vacation rentals in Baileys Harbor?
Yes, we offer vacation rentals close to top attractions in Baileys Harbor, or you can select a secluded option if you'd like a relaxing place to stay. Visitors to Baileys Harbor speak positively about the scenic lakeside and top-notch restaurants in this destination. Allow some time to check out the shops during your trip.
How many vacation rentals will I find in Baileys Harbor?
Expedia has 67 vacation rentals for your stay in Baileys Harbor.
What can I see and do in Baileys Harbor?
Lake Michigan and Kangaroo Lake are a couple of scenic spots to enjoy the outdoors, whereas Door Shakespeare is one of the cultural attractions. Door County Brewing Company and Stone's Throw Winery are other places to visit while you're in town.
What are vacation rentals like in Baileys Harbor?
Vacation rentals are privately owned properties you can stay in for several days or longer in Baileys Harbor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family gatherings.

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