Baileys Harbor holiday lettings

We found 730 holiday rentals — enter your dates for availability

Select from 66 houses, 15 flats and other holiday rentals to find the perfect place for your stay in Baileys Harbor. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, which might include a garden and Wi-Fi. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Baileys Harbor

Showing deals for:5 Jun - 12 Jun

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

7% off
Price is £4,283
for 7 nights, 1 home
£612 per night
includes taxes & fees
The Lookout, near Sister Bay with Starlink internet

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Why visit Baileys Harbor

  • Stunning natural beauty: Baileys Harbor boasts breathtaking scenery, perfect for outdoor enthusiasts and nature lovers.
  • Charming galleries: Explore the local art scene with delightful galleries showcasing regional talent.
  • Historic lighthouses: Visit iconic lighthouses that offer a glimpse into the area's maritime history.
  • Family-friendly beaches: Enjoy relaxing days on picturesque beaches, ideal for family outings.
  • Varied accommodation options: Find a range of charming rentals, from cosy cottages to spacious homes, catering to all needs.

Popular types of accommodation in Baileys Harbor

Welcome to Baileys Harbor, where Vrbo offers a delightful selection of holiday rentals to suit every traveller's needs. From charming cottages to spacious houses and cosy cabin rentals, there’s something for everyone. Whether you’re seeking a romantic getaway or a family retreat, our Baileys Harbor cottage rentals provide the perfect base for exploring this picturesque destination. Make your next holiday memorable with the ideal accommodation that promises comfort and convenience.

  • Houses: The top choice for visitors to Baileys Harbor, these homes offer a spacious and personalised retreat for families and groups.
  • Condos: A popular option for those seeking modern amenities and convenience, ideal for couples or small families.
  • Cottages: These quaint and charming dwellings provide a delightful and homely atmosphere for a relaxing getaway.
  • Cabins: Perfect for nature enthusiasts, these rustic lodgings offer a serene escape amidst the woods.
  • Apartments: A practical choice for solo travellers or couples, providing all the comforts of home in a compact space.**

Top attractions in Baileys Harbor

Baileys Harbor, Wisconsin, offers a delightful blend of outdoor activities, stunning scenery, and romantic getaways. Visitors can explore beautiful beaches, charming galleries, and historic lighthouses, making it an ideal destination for those seeking culture and adventure. Whether you're travelling solo or with loved ones, Baileys Harbor caters to all, promising a memorable experience amidst nature's splendour.

  • Cana Island Lighthouse: A historic lighthouse that offers a glimpse into maritime history. Climb to the top for stunning views of Lake Michigan and enjoy the cultural ambiance surrounding the area.
  • Kangaroo Lake: A picturesque lake perfect for romantic outings, featuring lovely beaches and scenic landscapes. Ideal for outdoor activities such as swimming, kayaking, and picnicking.
  • Baileys Harbor Ridges Park: An eco-friendly park that’s perfect for families, offering trails for hiking and birdwatching amidst beautiful natural surroundings, making it a great spot for a day out.

Things to do recommended for couples

For a romantic getaway in Baileys Harbor, enjoy a delightful wine tasting at Stone's Throw Winery or Harbor Ridge Winery, both offering a charming atmosphere. Don't miss the enchanting performances at Birch Creek Music Performance Center, just a short drive away, perfect for an entertaining evening together.

Things to do recommended for families

Families visiting Baileys Harbor can explore the serene Ridges Sanctuary for a relaxing day amidst nature, and for a bit of adventure, the Egg Harbor Fun Park, located 5.0km away, offers thrilling karting experiences that are sure to delight children and adults alike.

Things to do recommended for groups

Experience the local charm at Door County Brewing Company for a delightful brewery visit, enjoy a show at the Door Community Auditorium, or relish a classic film at The Skyway Drive-In Theatre. Each venue offers a unique atmosphere perfect for group enjoyment.

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

If you're travelling with a group, family, pets, or seeking longer stays, it's important to filter your options according to your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Baileys Harbor with a group: Think about how many bedrooms you require, as well as any amenities like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily apply filters for these features and many others on Vrbo.
  • Traveling to Baileys Harbor with young kids: Journeying with young children can pose its difficulties. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming 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, a family holiday isn’t truly enjoyable without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Baileys Harbor: If you're in search of holiday rentals offering discounts 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 such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Baileys Harbor

Baileys Harbor offers a delightful escape for those seeking relaxation amidst stunning scenery. With its charming waterfront and friendly atmosphere, it’s perfect for family vacations. Venture to nearby Sister Bay for more picturesque views and excursions that showcase the natural beauty of Wisconsin. Whether you’re indulging in leisurely strolls or enjoying outdoor activities, this idyllic destination promises a memorable experience for all visitors.

  • Ephraim: Located 4.3km from Baileys Harbor, Ephraim is a charming town renowned for its stunning outdoor scenery and romantic atmosphere. Visitors are drawn to its recreational areas, where one can indulge in activities like hiking and golfing amidst breathtaking landscapes. The town is nearby notable landmarks such as the picturesque lakes and the scenic national state park, making it a perfect spot for nature enthusiasts. With its serene beaches, Ephraim offers a tranquil retreat for couples and families alike.
  • Jacksonport: Also situated 4.3km from Baileys Harbor, Jacksonport is a delightful village that attracts visitors seeking outdoor adventures and picturesque views. The area is well-known for its extensive trail access, ideal for walking, cycling, and exploring the natural beauty around the local parks. Jacksonport’s proximity to serene lakes and the national state park enhances its appeal, providing ample opportunities for relaxation and recreation. It’s an idyllic setting for those wanting to immerse themselves in nature.
  • North Bay: Nestled in the vicinity of Baileys Harbor, North Bay is a quaint village that invites travellers to enjoy its outdoor charm and scenic surroundings. The area boasts accessible recreational venues, including golf courses and inviting beaches. Visitors can explore the nearby national state park, where opportunities for hiking and wildlife spotting abound. North Bay’s stunning lakeside views make it a romantic getaway, perfect for couples looking to unwind in a beautiful, natural 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

Are you aiming to cut costs on your upcoming journey? We recommend being open to adjusting your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To help you discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers you a handy platform to plan new getaways, resume your previous arrangements, or manage your travel itinerary. You can easily find the properties you've saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the relaxing 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, cycling and restaurants. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Baileys Harbor

Do you want to find top things to see and do in the city? Travellers enjoy Baileys Harbor for its hiking, cycling and kayaking. Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Baileys Harbor a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Stone's Throw Winery (3.4 mi / 5.4 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)
  • The Orchards at Egg Harbor (6.4 mi / 10.3 km)
  • Peninsula State Park Golf Course (6.7 mi / 10.8 km)

Exploring the natural features in Baileys Harbor

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Baileys Harbor is a great place to get outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • 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 when booking a holiday rental?
When considering the best area to stay in Baileys Harbor, Wisconsin, for a holiday rental, the charming neighbourhood near the waterfront is an excellent choice. This area offers a delightful blend of natural beauty and local attractions. One of the top highlights is the scenic Baileys Harbor Range Lights, where visitors can explore the historic lighthouses and enjoy stunning views of Lake Michigan. Additionally, the nearby Ridges Sanctuary is superb for nature enthusiasts, offering a unique opportunity to experience diverse ecosystems and various hiking trails.

In terms of accommodation, this waterfront area has a variety of properties available, ranging from quaint cottages to spacious homes, allowing for a comfortable stay that suits different group sizes and preferences.
How much does it cost to rent a holiday home in Baileys Harbor?
Prices for holiday 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 holiday 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, the area along the shores of Lake Michigan is particularly appealing. The waterfront properties near the Baileys Harbor Range Lights offer stunning views and easy access to the beach, making them great for families or groups looking to enjoy a lakeside getaway. Many of these rentals come equipped with amenities like spacious decks, outdoor grills, and private fire pits, ideal for evening gatherings under the stars.

The nearby Door County Land Trust preserves, such as the Toft Point Nature Preserve, provide opportunities for hiking and exploring the natural beauty of the region, and some properties in the vicinity offer direct access to nature trails. Additionally, you can find charming cottages and homes peppered throughout the area, some featuring modern kitchens, comfortable living spaces, and even kayaks or bikes available for guest use, allowing for a more adventurous stay.

Moreover, Baileys Harbor boasts local attractions such as small shops and restaurants, which enhance the convenience for visitors. Rentals in this area often combine rustic charm with modern comforts, creating a delightful experience for those looking to relax by the lake while enjoying the natural surroundings and local culture.
What is the most popular type of holiday rental accomodation in Baileys Harbor?
In Baileys Harbor, holiday houses are the most common type of holiday rental, with around 256 available throughout the area. These properties typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the beautiful Wisconsin surroundings. Many are situated near local attractions like the picturesque Lake Michigan shoreline and the scenic trails of the nearby nature preserves.

Cottages are also quite popular, with about 76 options that provide a charming, rustic feel, ideal for those seeking a quaint escape. They generally come with kitchen facilities and cosy living areas, superb for relaxing after a day of exploring. Additionally, there are around 60 condos and 44 cabins available, suiting various group sizes and preferences.
Are there any family house rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are numerous family-friendly holiday rentals available, with around 95 options to choose from. This charming locale offers a variety of homes superb for families, many of which are situated near the stunning shores of Lake Michigan. Visitors can expect spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for children to play and explore.

Properties often come with amenities such as private decks, BBQ grills, and even fire pits for evening gatherings. Families can enjoy nearby attractions like the scenic Door County Coastal Byway or the beautiful Ridges Sanctuary, which features nature trails and opportunities for wildlife observation. Additionally, the area is known for its quaint shops and local eateries, providing a taste of the region's unique charm.
Can I rent a holiday home with a pool or hot tub in Baileys Harbor?
In Baileys Harbor, there are several holiday homes available for rent that feature pools and hot tubs, with around 15 options to choose from. This charming area, located on the Door County Peninsula, is known for its picturesque landscapes and proximity to Lake Michigan. Many of these properties come equipped with amenities such as private pools, hot tubs, outdoor patios, and fully equipped kitchens, making them great for relaxation and family gatherings.

Travellers can enjoy the serene surroundings while having access to various recreational activities, including hiking, fishing, and exploring nearby parks.
Can I find long-stay holiday rentals in Baileys Harbor?
A long-stay holiday rental in Baileys Harbor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Baileys Harbor?
In Baileys Harbor, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these holiday homes feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam and play. Some properties even include fenced yards and nearby walking paths, ensuring that both guests and their pets enjoy a comfortable stay.

The area is known for its stunning natural scenery, including the nearby Door County Parks, which offer trails and open spaces superb for walking and exploring with pets. The picturesque waterfront along Baileys Harbor provides opportunities for outdoor activities like kayaking and fishing, making it an excellent choice for those looking to enjoy nature with their pets.
Are there any remote work holiday rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are approximately 400 remote work-friendly holiday rentals available, making it an excellent choice for those who wish to combine work and leisure. Many of these properties are equipped with reliable Wi-Fi, ensuring that you can stay connected while enjoying the tranquillity of this beautiful area.

Travellers can expect a variety of amenities, including comfortable workspaces, spacious living areas, and fully equipped kitchens, allowing for a relaxed and productive stay. The scenic surroundings offer plenty of opportunities for outdoor activities, such as hiking and exploring local parks, providing a refreshing break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Baileys Harbor holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Baileys Harbor with parking available—perfect for families or travellers 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, holiday rentals typically offer a range of popular amenities that enhance the comfort of travellers. Most properties include fully equipped kitchens, allowing guests to prepare their own meals. Many also feature decks or patios where visitors can relax and enjoy the beautiful surroundings. For those chilly evenings, fireplaces provide a warm and inviting atmosphere. Onsite parking is commonly available, making it convenient for guests with vehicles. Additionally, many rentals come with coffee and tea makers, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Baileys Harbor for a holiday rental?
The best time to visit Baileys Harbor for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This is when the area comes alive with outdoor activities, including kayaking, hiking, and exploring the stunning landscapes of Door County. The warm summer temperatures, typically ranging from 15 to 30 degrees Celsius, provide a comfortable setting for enjoying the beautiful beaches and charming local attractions.

In addition to outdoor adventures, July offers numerous festivals and events that highlight the vibrant local culture, making it an ideal month for those looking to immerse themselves in the community spirit. Families and friends will find plenty of opportunities for fun and relaxation, whether it's taking a boat tour or visiting the picturesque lighthouses that dot the coastline.

If you're seeking a more budget-friendly option, consider planning your visit in November. While this time of year is quieter, it offers a unique chance to enjoy the tranquil beauty of Baileys Harbor as the fall colours give way to a peaceful winter landscape. This serene atmosphere is superb for those looking to unwind and appreciate the natural surroundings without the hustle and bustle of the peak season.
How early should I book a Baileys Harbor holiday rental?
Book your Baileys Harbor holiday 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 holiday 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 range of attractions that highlight the area's natural beauty and charming local culture. The Baileys Harbor Range Lights, a pair of historic lighthouses, offer picturesque views and insights into the maritime history of the region. Nearby, the scenic Door County Coastal Byway provides stunning vistas of Lake Michigan and is great for leisurely drives or cycling.

For outdoor enthusiasts, the beautiful Door County Land Trust preserves several natural areas where you can hike and explore the local flora and fauna. The Ridges Sanctuary, known for its unique ecosystems and diverse wildlife, is a must-visit for nature lovers and photographers alike.
Can I change or cancel my Baileys Harbor home rental booking on Vrbo?
To find Baileys Harbor holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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