Best Vacation Homes in Baileys Harbor
House
10.0(254 Reviews)
2 Bedrooms
2 Baths
7 Guests
1200 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $522/Night
7 Nights - US $3,654
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1496.18 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $594/Night
7 Nights - US $4,158
Cabin
8.2(168 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Kitchen
Parking
US $241/Night
7 Nights - US $1,687
House
10.0(223 Reviews)
2 Bedrooms
2 Baths
7 Guests
2026 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $533/Night
7 Nights - US $3,734
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
10763.91 ft²
- Balcony/Terrace
Breakfast
Pet Friendly- Kitchen
US $416/Night
7 Nights - US $2,912
Cabin
10.0(141 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $339/Night
7 Nights - US $2,376
Cottage
10.0(99 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $454/Night
7 Nights - US $3,176
House
10.0(76 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $584/Night
7 Nights - US $4,089
Baileys Harbor Luxury Rentals
House
7.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
3498.27 ft²
- View
- Parking
Internet
Child Friendly
US $2,029/Night
7 Nights - US $14,204
House
4 Bedrooms
4 Baths
14 Guests
4402.44 ft²
- View
- Parking
Air Conditioner- Internet
US $2,009/Night
7 Nights - US $14,061
House
9.6(19 Reviews)
6 Bedrooms
7 Baths
14 Guests
5500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,854/Night
7 Nights - US $12,975
Villa
10.0(25 Reviews)
7 Bedrooms
4 Baths
19 Guests
Spa- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,718/Night
7 Nights - US $12,029
House
5 Bedrooms
4 Baths
18 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,707/Night
7 Nights - US $11,951
Cottage
10.0(25 Reviews)
4 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $1,654/Night
7 Nights - US $11,577
Cabin
9.2(19 Reviews)
4 Bedrooms
4 Baths
14 Guests
4400 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $1,527/Night
7 Nights - US $10,688
House
4 Bedrooms
3 Baths
8 Guests
4000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,493/Night
7 Nights - US $10,453
Baileys Harbor Pet Friendly Vacation Rentals
House
10.0(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
US $465/Night
7 Nights - US $3,254
House
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
2723.27 ft²
- Spa
- Fireplace/Heating
- View
- Pet Friendly
US $716/Night
7 Nights - US $5,010
Cabin
10.0(5 Reviews)
1 Bedroom
1 Bath
4 Guests
760 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $300/Night
7 Nights - US $2,097
House
9.0(3 Reviews)
1 Bedroom
1 Bath
6 Guests
721.18 ft²
- Spa
- Fireplace/Heating
- View
- Pet Friendly
US $104/Night
7 Nights - US $728
Cabin
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
450 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $428/Night
7 Nights - US $2,998
Cabin
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $519/Night
7 Nights - US $3,634
House
9.8(72 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $357/Night
7 Nights - US $2,497
Cabin
9.6(105 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $299/Night
7 Nights - US $2,090
Baileys Harbor Large Vacation Homes
House
10.0(134 Reviews)
4 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $846/Night
7 Nights - US $5,919
House
10.0(1 Review)
5 Bedrooms
4 Baths
6 Guests
5005.22 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $1,159/Night
7 Nights - US $8,116
House
10.0(92 Reviews)
6 Bedrooms
3 Baths
12 Guests
3600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,307/Night
7 Nights - US $9,150
House
8.1(45 Reviews)
9 Bedrooms
5 Baths
28 Guests
600.63 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $123/Night
7 Nights - US $861
House
10.0(81 Reviews)
4 Bedrooms
4 Baths
16 Guests
3500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,262/Night
7 Nights - US $8,833
House
10.0(73 Reviews)
5 Bedrooms
2 Baths
10 Guests
2479 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $758/Night
7 Nights - US $5,303
House
10.0(72 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,003/Night
7 Nights - US $7,018
House
10.0(32 Reviews)
5 Bedrooms
4 Baths
6 Guests
5000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $879/Night
7 Nights - US $6,153
Why Choose Rent By Owner for your Baileys Harbor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Baileys Harbor
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you make the most of your stay in this charming destination, where seasonal changes influence the ambiance and activities available throughout the year.
Peak Season Highlights
Summer (June to August)
During the warm months, you can enjoy ideal weather for outdoor activities and scenic views, making it the most popular time to visit the area.
Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F
Fall (September to November)
Autumn offers vibrant foliage and pleasant temperatures, perfect for exploring the region’s natural beauty and enjoying a peaceful retreat.
Average Temperature Daytime: 60-70°F - Nighttime: 45-50°F
Off-Season Highlights
Spring (March to May)
Early spring brings mild weather and fewer visitors, giving you a more relaxed experience as nature begins to bloom.
Average Temperature Daytime: 50-65°F - Nighttime: 35-45°F
Winter (December to February)
The winter months feature colder temperatures and snow, ideal for those seeking a cozy getaway and wintertime tranquility.
Average Temperature Daytime: 20-30°F - Nighttime: 10-20°F
Weekly Weather Forecast for Baileys Harbor
How to Book Your Baileys Harbor Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Baileys Harbor
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private outdoor spaces such as patios, decks, or yards for relaxing and entertaining.
- Take advantage of outdoor cooking facilities including grills or BBQ areas for preparing local cuisine.
- Benefit from well-maintained gardens or landscaped areas that enhance the natural beauty of your stay.
- Make the most of scenic views offered by waterfronts, gardens, or nearby parks within the property.
- Utilize outdoor dining spaces designed for enjoying meals amidst the tranquil surroundings.
- Access shared or individual fire pits for cozy evenings under the stars.
- Explore outdoor recreational amenities like hammocks, picnic tables, or lounging areas perfect for leisure activities in the region.
Top Attractions Around Baileys Harbor
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities such as kayaking, hiking, and exploring local parks, providing the perfect backdrop for a relaxing and adventurous stay in Baileys Harbor, Wisconsin.
Family Activities
- Door County Maritime Museum: Discover the region's rich maritime history and enjoy interactive exhibits that captivate children and adults alike.
- Baileys Harbor Range Lights: Take a family stroll to these historic lighthouse lights for picturesque views and educational opportunities about local maritime safety.
- Nearby State Parks: Explore scenic outdoor adventures, including hiking, picnicking, and wildlife viewing, perfect for family bonding in the area.
- Local Beaches: Relax on pristine shores and build sandcastles with your loved ones while soaking up the peaceful lakeside atmosphere.
Adult Activities
- Kayaking and Paddleboarding: Explore the scenic waters of the region by enjoying a kayak or paddleboard adventure, offering you a peaceful way to experience the area's natural beauty.
- Bird Watching and Nature Walks: Discover the diverse bird species and plant life through guided or self-led nature walks in the region's protected parks and reserves.
- Wine Tasting Tours: Visit local wineries and tasting rooms in the region to sample regional wines while enjoying the picturesque countryside surrounding your stay.
Other Places to Stay in Baileys Harbor, WI
Door County
Door Shakespeare
Kangaroo Lake
Stone's Throw Winery
Birch Creek Music Performance Center
Anclam Beach Park
Door County Brewing Company
Baileys Harbor Ridges Park
Ridges Sanctuary
North Bay
Cana Island Lighthouse
Baileys Harbor Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the charming eateries and boutiques nearby to experience the area's unique charm and support local businesses.
- Visit Natural Attractions: Make time to enjoy the scenic outdoor spots in the region, which are perfect for relaxing walks or outdoor activities during your stay.
- Plan Seasonal Activities: Check out seasonal events and outdoor pursuits available here to add memorable experiences tailored to your travel dates.
- Utilize Waterfront Proximity: Choose properties close to the waterfront to easily access boating, fishing, or simply unwinding by the water’s edge during your visit.
Transportation Options
- Personal Vehicles: Renting a car is a convenient way to explore the region and access your vacation rentals with ease, especially if you're planning to visit multiple attractions in Baileys Harbor.
- Local Taxis and Rideshare Services: Taxis and rideshare options like Uber or Lyft provide flexible transportation within the area, allowing you to get around comfortably without the need for a personal vehicle.
- Public Transportation: Local bus services connect key points of interest and facilitate easy travel for visitors seeking economical transit options throughout this destination.
- Bicycle Rentals: Biking offers an eco-friendly and leisurely way to experience the scenic beauty of the area while accessing nearby vacation rentals and outdoor attractions.
Local Customs Options
- Traditional Fish Boil: Participating in the local fish boil is a cherished custom, where fresh catches are cooked outdoors with potatoes and onions, embodying the region’s maritime heritage.
- Harbor Fest Celebrations: During this festive time, locals gather to enjoy music, food, and parades that highlight the area's strong community spirit and maritime traditions.
- Seasonal Wildlife Observation: Respect for the local environment is evident through the community’s emphasis on observing seasonal bird migrations and native wildlife, accessible from your vacation rental here.
- Respectful Shoreline Practices: Maintaining the pristine shorelines is a shared value, with visitors encouraged to follow proper disposal and conservation practices in this coastal destination.
Frequently Asked Questions About Baileys Harbor?
1. What are the top vacation rentals in Baileys Harbor?
There are a lot of options in Baileys Harbor. If you plan on staying in the Baileys Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Baileys Harbor:
- Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!
- Wild Cedars - Cana Island - Lake Michigan - Amazing new home
- Door County Cabin in the Woods, Baileys Harbor
- Lakefront! 5 Star Home on the Bay! Waterfront Property with 200ft of Shoreline.
- Perfect for families!, Baileys Harbor 3 Bedroom House! Sleeps 6 plus 2 under 12
- Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
- Luxury lakefront home - 6 BRs, kids, pets, EVs, elevator - family celebrations
- Peace And Tranquility Setting In The Woods!
- Island View Lake House K Lake
- Downtown Baileys Harbor Retreat · Walk to Dining
2. Which vacation homes in Baileys Harbor are best for families?
If you are looking for a family-friendly vacation home in Baileys Harbor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Baileys Harbor:
3. How many Rentbyowner vacation rentals are available in Baileys Harbor?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 236 in the Baileys Harbor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Baileys Harbor.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual listing. You should review the specific property's cancellation terms on the booking page or contact the property owner directly to ensure you're comfortable with the policy before confirming your reservation.
5. Are there any additional fees or charges for booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes are often itemized on the listing page. Make sure to carefully review all costs associated with your reservation before completing your booking to avoid surprises.
6. How do I confirm the availability of a vacation rental in this destination?
Availability is updated regularly on the booking platform. To confirm a property’s availability, you should check the calendar on the listing and consider reaching out to the property owner for confirmation or special requests.
7. What are the check-in and check-out procedures for vacation rentals here?
Check-in and check-out details are typically provided within the listing or communicated directly by the owner. It’s best to review these procedures in advance to plan your arrival and departure accordingly.
8. Is there a minimum stay requirement for booking a vacation rental in this region?
Many properties have minimum stay requirements that can vary by listing and season. To find out the specific requirements, review the booking details on the listing or contact the owner directly before making your reservation.
Baileys Harbor Top Rated Vacation Rentals
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
Pool
US $508/Night
7 Nights - US $3,559
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $239/Night
7 Nights - US $1,676
Resort
9.4(212 Reviews)
21 Baths
70 Guests
643.3 ft²
Private Beach- Oceanfront
- Hot Tub
- Fireplace/Heating
US $409/Night
7 Nights - US $2,863
Hotel
9.0(117 Reviews)
21 Baths
480.78 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $194/Night
7 Nights - US $1,358
Hotel
8.8(144 Reviews)
73 Baths
608.35 ft²
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
US $112/Night
7 Nights - US $784
Condo
6.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $239/Night
7 Nights - US $1,676
Apartment
5 Bedrooms
4 Baths
14 Guests
1399.31 ft²
- Private Pool
- Hot Tub
Skiing- Fireplace/Heating
US $1,474/Night
7 Nights - US $10,318
Condo
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $497/Night
7 Nights - US $3,480
