Baileys Harbor holiday rentals

We found 789 holiday rentals — enter your dates for availability
Select from 70 houses, 21 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:11 Dec - 18 Dec

Indulge yourself with Italian marble and Egyptian cotton
From the deck outside the master bedroom
Plenty of space and light
Delicious meals start here!
Exceptional
(129 reviews)

As seen in Door County Magazine! Private, Family Friendly, Sat TV, WiFi

Fish Creek

12% off
AU$4,657
for 7 nights, 1 chalet
AU$665 per night
includes taxes & fees
As seen in Door County Magazine! Private, Family Friendly, Sat TV, WiFi
View driving up driveway towards house.
View from lower deck
Private kitchen
Interior
Exceptional
(136 reviews)

Lakefront!! 5 Star Home on the Bay! Waterfront Property with 200ft of Shoreline.

Egg Harbor

8% off
AU$5,302
for 7 nights, 1 home
AU$757 per night
includes taxes & fees
Lakefront!! 5 Star Home on the Bay! Waterfront Property with 200ft of Shoreline.
Staircase to the 2nd Floor
Soaring Vaulted Beamed Ceiling
Open Concept Floor Plan, New Construction 2024!
Thanks for looking. Please contact us with any questions.
Exceptional
(108 reviews)

Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

Baileys Harbor

6% off
AU$3,098
for 7 nights, 1 cottage
AU$443 per night
includes taxes & fees
Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
plenty of seating
Deck is accessible off the hallway and bedroom
Living area
Property backs directly to Mink River nature conservancy!
Exceptional
(34 reviews)

The Lookout, minutes to Sister Bay with Starlink internet

Ellison Bay

7% off
AU$6,947
for 7 nights, 1 home
AU$992 per night
includes taxes & fees
The Lookout, minutes to Sister Bay with Starlink internet
Living Room
Back patio
Dining
Exterior detail
Exceptional
(35 reviews)

Cozy Cabin located minutes from Whitefish Dunes Park

Sturgeon Bay

8% off
AU$3,781
for 7 nights, 1 cabin
AU$540 per night
includes taxes & fees
Cozy Cabin located minutes from Whitefish Dunes Park
Bedroom #1
Dining Room/Kitchen/Living Room
Dining Room
Kitchen
Exceptional
(31 reviews)

4 Master Suite Home Sleeps 12 w/Hot Tub in Door Co

Egg Harbor

7% off
AU$7,411
for 7 nights, 1 home
AU$1,059 per night
includes taxes & fees
4 Master Suite Home Sleeps 12 w/Hot Tub in Door Co
House #1 - Dining area
House #1 - Dining area, kitchen and living room
House #2 exterior
House #2 - Entry
Exceptional
(8 reviews)

2 Neighboring Homes Sleep 24 - 8 Bedrooms/10 Baths

Egg Harbor

8% off
AU$14,387
for 7 nights, 1 home
AU$2,055 per night
includes taxes & fees
2 Neighboring Homes Sleep 24 - 8 Bedrooms/10 Baths
Welcome to Nest By The Bay in beautiful Egg Harbor, WI - right off Hwy 42!
Kitchen island includes seating for 4
Master bedroom with king bed & full bath - access to back porch
Back patio with grill, patio chairs, and table overlooking woods & creek
Exceptional
(22 reviews)

New 4BR Egg Harbor Home: Walk to Downtown + 2 Min Drive to Egg Harbor Beach

Egg Harbor

8% off
AU$5,846
for 7 nights, 1 home
AU$835 per night
includes taxes & fees
New 4BR Egg Harbor Home: Walk to Downtown + 2 Min Drive to Egg Harbor Beach
Kitchen
Dining Area/Kitchen/Living Room
Dining Area
Exterior
Exceptional
(24 reviews)

5 Bed, 6 Bath Home Sleeps 24 w/Hot Tub in Door Co.

Egg Harbor

7% off
AU$7,585
for 7 nights, 1 home
AU$1,084 per night
includes taxes & fees
5 Bed, 6 Bath Home Sleeps 24 w/Hot Tub in Door Co.
Room
You will love it here!
Living area
Exterior
Exceptional
(369 reviews)

Gingerbread Cottage - Forest Setting - Available Winter Too!

Fish Creek

9% off
AU$2,683
for 7 nights, 1 cottage
AU$383 per night
includes taxes & fees
Gingerbread Cottage - Forest Setting - Available Winter Too!
Dining
Living area
Exterior
Living area
Exceptional
(9 reviews)

Stunning Luxury Home on the Sandy Beach Shores of Lake Michigan!!

Sturgeon Bay

8% off
AU$10,392
for 7 nights, 1 home
AU$1,485 per night
includes taxes & fees
Stunning Luxury Home on the Sandy Beach Shores of Lake Michigan!!
Staircase to second floor
Relax and "hang out" on the covered front porch. Two hanging chairs and sofa
Dining table seats up to 8 plus 4 bar stools
Main living space with natural wood burning fire place
Exceptional
(30 reviews)

Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach

Ellison Bay

7% off
AU$4,761
for 7 nights, 1 home
AU$680 per night
includes taxes & fees
Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
Living room
Property grounds
Exterior
Living room
Exceptional
(78 reviews)

NEW Private 3 acre waterfront property directly on the Bay! WEEKLY DISCOUNT 10%

Sturgeon Bay

7% off
AU$6,575
for 7 nights, 1 home
AU$939 per night
includes taxes & fees
NEW Private 3 acre waterfront property directly on the Bay! WEEKLY DISCOUNT 10%
Enjoy an eat-in kitchen, perfectly situated to prepare all of your basic meals and snacks.
During your stay, you'll have privileged access to a range of amenities. Start your day with sumptuous dining at the club's exquisite restaurants, where every meal becomes a memorable experience. Overlooking the 18th green and the waters of Green Bay
Bedroom #1 boasts a comfortable king sized and large whirlpool tub with en suite bathroom.
Experience the ultimate convenience and relaxation at our Club Cottages, nestled within the enchanting Horseshoe Bay Golf Club. Our exclusive collection boasts five elegant 2-bedroom, 2-bathroom condos, each featuring a cozy fireplace and a whirlpoo
Very good
(5 reviews)

Horseshoe Bay #3- Private Golf Club Access!

Egg Harbor

7% off
AU$2,642
for 7 nights, 1 apartment
AU$377 per night
includes taxes & fees
Horseshoe Bay #3- Private Golf Club Access!
Living area
Private kitchen
Exterior
Private kitchen
Exceptional
(69 reviews)

Egg Harbor White House - 4 bedroom

Egg Harbor

7% off
AU$2,788
for 7 nights, 1 home
AU$398 per night
includes taxes & fees
Egg Harbor White House - 4 bedroom
Exterior
Screen porch
Room
Dining
Exceptional
(6 reviews)

Jacksonport Woodland Hearth Retreat - Near Lake Michigan

Sturgeon Bay

7% off
AU$2,719
for 7 nights, 1 cabin
AU$388 per night
includes taxes & fees
Jacksonport Woodland Hearth Retreat - Near Lake Michigan
walk to our beach and view the marina
park and marina picture as we walked into the village for dinner.
Larsen House Exterior Remodeled 6/2015
Interior
Excellent
(98 reviews)

2025 Beautiful Remodel-Outstanding Location Near Excellent Attractions!

Egg Harbor

8% off
AU$3,953
for 7 nights, 1 home
AU$565 per night
includes taxes & fees
2025 Beautiful Remodel-Outstanding Location Near Excellent Attractions!
Living area
Terrace/patio
Interior
Living area
Exceptional
(31 reviews)

Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay

Ellison Bay

7% off
AU$4,295
for 7 nights, 1 home
AU$614 per night
includes taxes & fees
Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
New kitchen with quartz countertops and counter-seating
Watch the nightly sunset from our Andirondack chairs
Living area
Exterior
Exceptional
(24 reviews)

Enjoy nightly sunsets at this Beautiful Door County Waterfront Home

Sturgeon Bay

8% off
AU$8,324
for 7 nights, 1 home
AU$1,189 per night
includes taxes & fees
Enjoy nightly sunsets at this Beautiful Door County Waterfront Home
Private kitchen
Living area
Terrace/patio
Room
Exceptional
(105 reviews)

DOOR 42! Minutes away from the hustle and bustle of Sister Bay!

Sister Bay

7% off
AU$4,602
for 7 nights, 1 home
AU$657 per night
includes taxes & fees
DOOR 42! Minutes away from the hustle and bustle of Sister Bay!
Front yard
Front of house views
Kitchen table
Front porch views
Exceptional
(16 reviews)

Charming, Cozy Farmhouse! Newly renovated with plenty of sleeping space.

Egg Harbor

8% off
AU$5,758
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Charming, Cozy Farmhouse! Newly renovated with plenty of sleeping space.
Living area
Outdoor dining
Living area
Private kitchen
Exceptional
(15 reviews)

Luxury A-Frame w/ Lake Access, Great For Families

Egg Harbor

8% off
AU$5,998
for 7 nights, 1 home
AU$857 per night
includes taxes & fees
Luxury A-Frame w/ Lake Access, Great For Families
Interior
Exterior detail
Deck entrance in Summer and Fall
Interior
Very good
(15 reviews)

Three Sister Meadow "Sweet" Retreat

Sister Bay

8% off
AU$3,237
for 7 nights, 1 room
AU$462 per night
includes taxes & fees
Three Sister Meadow "Sweet" Retreat
Open concept living room dining room and kitchen area
Parking in front of the door! blue Horse Cafe in the background.
Kitchen Island & Main Bath
Open concept kitchen with bar seating
Exceptional
(138 reviews)

Prime Location & Highly Rated Dog Friendly Cottage with 'Perks'

Fish Creek

11% off
AU$1,422
for 7 nights, 1 cottage
AU$203 per night
includes taxes & fees
Prime Location & Highly Rated Dog Friendly Cottage with 'Perks'

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • Cave Point County Park (9.6 mi / 15.4 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)
  • Peninsula State Park Golf Course (6.7 mi / 10.8 km)
  • Egg Harbor Fun Park (8.5 mi / 13.7 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:

  • Baileys Harbor Ridges Park (0.5 mi / 0.8 km)
  • Kangaroo Lake (2.8 mi / 4.5 km)
  • Ephraim Public Beach (6.4 mi / 10.3 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Baileys Harbor holiday homes prices shown on Stayz?
Stayz 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.
Are there any Baileys Harbor holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Baileys Harbor holiday homes?
You can find great discounts on holiday homes in Baileys Harbor on Stayz, 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.
Can I change or cancel my Baileys Harbor holiday home booking on Stayz?
To find Baileys Harbor holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Baileys Harbor?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Baileys Harbor holiday home?
Book your Baileys Harbor holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Baileys Harbor?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Baileys Harbor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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