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Baileys Harbor holiday lettings

We found 744 holiday rentals — enter your dates for availability

Select from 71 houses, 18 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:2 Jan - 9 Jan

Image gallery for Red Cherry Woods Cottage 🍒 New Construction!

Red Cherry Woods Upscale Retreat in Baileys Harbor Quiet Wooded Neighborhood
10 out of 10, Exceptional, (80 reviews)
Exceptional
(80 reviews)

Red Cherry Woods Cottage 🍒 New Construction!

Baileys Harbor, WI

7% off
Price is £1,455
for 7 nights, 1 cottage
£208 per night
includes taxes & fees
Red Cherry Woods Cottage 🍒 New Construction!

Find spaces that suit your style

Find out more about Baileys Harbor

Find out more about Baileys Harbor

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:

  • 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 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)
  • Waterfront Park (8.6 mi / 13.9 km)

Frequently asked questions

What is the best area to stay in Baileys Harbor when booking a holiday rental?
When considering a holiday rental in Baileys Harbor, an excellent area to stay in is the vicinity of the Baileys Harbor Waterfront. This charming neighbourhood offers a picturesque setting right by the stunning waters of Lake Michigan, making it an ideal spot for those who enjoy beautiful views and outdoor activities. Here, you can find a variety of properties ranging from cosy cottages to spacious homes that cater to various group sizes, with many options offering direct access to the water.

Staying near the waterfront also places you close to the Baileys Harbor Range Lights, a lovely historical site that adds a touch of charm to the area. In addition, the nearby Ridges Sanctuary is a must-visit, offering scenic trails and a chance to explore the unique flora and fauna of the region. This combination of natural beauty and local attractions makes the waterfront area an appealing choice for holidaymakers.
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 shoreline of Lake Michigan offers some wonderful options. The stretch near the Baileys Harbor County Park is particularly appealing, as it provides easy access to sandy beaches and scenic views of the water. Many properties in this region boast amenities such as spacious decks, outdoor grills, and picnic areas, making them great for families or groups looking to enjoy the outdoors.

Additionally, the vicinity around the Ridges Sanctuary is another excellent choice for beach rentals. Here, you can find charming cottages and modern homes that often feature large windows for natural light, fully equipped kitchens for self-catering, and some even include fire pits for evening gatherings. The Ridges Sanctuary offers beautiful hiking trails that lead to stunning landscapes, and rentals nearby typically provide easy access to these trails.
What is the most popular type of holiday rental accomodation in Baileys Harbor?
In Baileys Harbor, holiday houses are the most popular rental option, with about 69 available throughout the charming town. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces great for relaxing after a day of exploring the nearby Door County National Park or visiting local attractions like the Baileys Harbor Range Lighthouse. Additionally, there are around 20 cottages that provide a quaint and cosy atmosphere, ideal for couples or small families seeking a peaceful retreat. For those preferring a more modern stay, approximately 17 condos are also available, offering amenities such as pools and fitness centres, while a few cabins and several apartments can be found for those looking for a great experience.
Are there any family house rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are over a hundred family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features various neighbourhoods, each with its own charm, including proximity to the stunning Door County coastline and the picturesque landscapes of Lake Michigan. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play and explore.

Visitors can enjoy amenities such as private patios, game rooms for indoor entertainment, and sometimes even access to nearby beaches or hiking trails. The locale is also close to attractions like the Ridges Sanctuary, a beautiful nature preserve ideal for family hikes, and the Baileys Harbor Range Lights, which provide a bit of local history and scenic views.
Can I rent a holiday home with a pool or hot tub in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are several holiday homes available for rent that feature pools and hot tubs, with around 17 options to choose from. This picturesque area, located along the Door County shoreline, offers a blend of natural beauty and outdoor activities, making it a delightful destination for travellers. Many properties come equipped with private pools and hot tubs, as well as amenities such as spacious decks, outdoor seating areas, and fully equipped kitchens, great for families or groups looking to enjoy a relaxing getaway.
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, with around 50 options to choose from. This charming area, located on the scenic Door County peninsula, offers a delightful mix of natural beauty and accessibility to local attractions. Many holiday homes feature amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups travelling with pets.
Are there any remote work holiday rentals in Baileys Harbor?
In Baileys Harbor, Wisconsin, there are numerous remote work-friendly holiday rentals available, with around 105 options to choose from. This picturesque area, situated along the Door County coastline, offers a range of properties that cater to those looking to blend work and leisure. Many of these rentals are equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, desks, and comfortable chairs, ensuring a productive environment while enjoying the serene surroundings. 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, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many rentals also feature outdoor patios, great for enjoying the fresh air and stunning natural surroundings. Additionally, amenities such as cookware, dishware, and utensils are commonly provided, along with microwaves and stovetops for convenient cooking options.
When is the best time to visit Baileys Harbor for a holiday rental?
The most popular time to visit Baileys Harbor is during the peak summer months of June to August, particularly in July when the area truly comes alive. This vibrant season offers visitors an array of outdoor activities, including kayaking, hiking, and exploring the stunning Door County beaches, all set against a backdrop of warm weather and beautiful landscapes.

With average temperatures ranging from the high teens to low 20s Celsius, this is an ideal climate for enjoying the great outdoors. The long days provide ample time for sightseeing, whether you're wandering through charming local shops or taking a scenic boat tour in the picturesque waters of Lake Michigan.

For those looking to enjoy Baileys Harbor on a budget, November presents a wonderful opportunity. While it's considered low season, this month offers a quieter experience, superb for those who appreciate the tranquillity of nature. You can enjoy the fall colours and the peaceful atmosphere, making it an excellent time for leisurely walks along the shoreline or peaceful reflection in the natural surroundings.
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 local charm. The Baileys Harbor Range Lights, a historic lighthouse, offers picturesque views and a glimpse into the maritime history of the region. Nearby, the Ridges Sanctuary provides a unique opportunity for nature walks and birdwatching, with its diverse ecosystems and well-marked trails.
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 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 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.

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