Photo by ‎Staci Neidert

Baileys Harbor holiday lettings

We found 730 holiday rentals — enter your dates for availability

Select from 71 houses, 17 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:14 Nov - 21 Nov
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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 most popular type of holiday rental accommodation in Baileys Harbour?
The most desirable types of holiday rentals in Baileys Harbour are houses. After something a little different? Vrbo has many options to match our guests' diverse needs, so you'll see holiday homes in all sizes, and for all budgets. The perfect fit is ready and waiting for you — get hold of yours today.
How much does it cost to rent a holiday rental in Baileys Harbour?
The average price for a holiday rental in Baileys Harbour is based on several factors, such as length of stay, property type and season. Whether you're in search of a sprawling villa with space for extended family or an apartment for you and your other half, just enter your travel dates to see some great-value stays.
How much does it cost to rent a beach house in Baileys Harbour?
When you travel and the style and size of the property will influence the cost of your beachside holiday rental. Type in your Baileys Harbour travel dates to view your available options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday rentals in Baileys Harbour?
Yes. You'll have a choice of 82 holiday rentals that allow pets in Baileys Harbour on Vrbo. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly holiday rentals to book a property where your puppy dog can get in on the family fun.
What are popular rental amenities in Baileys Harbour?
When it comes to rental amenities that guests look for in Baileys Harbour, an electric car charging station, a water view and nearby museums are at the top of the list. With Vrbo holiday rentals, you'll discover options to suit your taste and style, whether you're taking a trip with your partner, your family or even pets.
Are there large group holiday rentals in Baileys Harbour?
There are 21 holiday rentals in Baileys Harbour that can host a group of 10 or more guests. Whether you're planning a trip with the family or an event like a party, there's plenty of room to get your loved ones together under the same roof.
Are there holiday rentals in Baileys Harbour that welcome kids?
Bring the entire group together for the adventure of a lifetime in Baileys Harbour at one of our 82 family-friendly holiday properties. A lot of these stays come with amenities that are suitable for getaways with youngsters, including dining rooms, extra bedrooms and entertainment units. Simply click on the "Properties good for families" filter box and pick your favourite option.
What are the top attractions for families in Baileys Harbour?
Keeping the kids happy during your Baileys Harbour holiday is a cinch with these leading family-friendly attractions:

  • Egg Harbour Beach
  • Sister Bay Beach
  • Fish Creek Public Beach

Are there one-bedroom holiday rentals in Baileys Harbour?
Yes, you can choose from five one-bedroom rentals in Baileys Harbour. Whether you're on the lookout for a comfy cottage or a cabin, Vrbo's one-bedroom rentals are just right if you don't need a huge amount of space. One of the main perks of having your own place? You won't need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Baileys Harbour?
Take your pick of 25 two-bedroom holiday homes in Baileys Harbour. Settle the kids into the second room or maybe fill it with a couple of your favourite people. There's enough space for whoever's lucky enough to come along for the ride.
Are there holiday rentals with WiFi in Baileys Harbour?
Whether you'd like to stay in touch with world events, write a few emails or post a pic to social media, there are 30 holiday homes with WiFi in Baileys Harbour. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Baileys Harbour?
You'll have your pick of 53 holiday rentals with air conditioning in Baileys Harbour offering that gentle, cool breeze and extra level of comfort. Simply enter your chosen travel dates and then use our filter tool to help you locate properties with air conditioning.
How old do you have to be to rent a holiday rental in Baileys Harbour?
The minimum required age is normally 16, 18 or 21. It can change across properties on Vrbo, so check the rules of your preferred Baileys Harbour holiday rental before booking.
How long can I rent a holiday rental in Baileys Harbour for?
It's up to the Baileys Harbour property. To browse a list of options offering extended stays, simply enter your travel dates and number of guests into Vrbo's search page. Enjoy having the place to yourself, along with the comforts of home like a fully-equipped kitchen and an outdoor space where the kids can run around and play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

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