House in Baileys Harbor, WI
14 guests · 6 bedrooms · 7 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Welcome to Our Lakeside Legacy, the house that our great grandparents built as some of the first settlers in Baileys Harbor. This loving, well cared for Brann family home has created many great memories for us and we are honored for you to make your own at this one-of-a-kind property, hosted by Simple Life Rentals. All five suites are ensuite – offering you the utmost comfort and privacy when vacationing with up to 14 of your family and friends.
Perfectly situated in the heart of town with over 150 feet of lake frontage in your backyard. The large yard offers expansive views of Baileys Harbor, the lighthouse, and Lake Michigan. Enjoy three levels of patios and decks, all lake facing, to take in the incredible views. Plus, a classic, town facing covered front porch is the perfect spot to watch the folks walking by as they move around town. This heart of town location is steps from some of Door County’s finest dining, breweries, shops, marina, kayaking, charter fishing, and beaches.
Property Features:
+ 150 feet of Lake Michigan waterfront
+ Over 5000 square feet of living space!
+ One 65" Smart TV in main level living room, streaming content via Roku and equipped with a DVD player. Guests may log in using own account.
+ 4 spacious living spaces on the first level, offering versatile areas for relaxation and socializing
+ 2 dedicated work areas (parlor on the first level and primary suite on second level)
+ 3 fireplaces for aesthetics only, not for guest use
+ T-Mobile Home Internet service is available for reliable connectivity throughout your stay
+ Hot water heat throughout the home
+ Mitsubishi cooling appliances in each of the living spaces
+ Washer, dryer, iron, ironing Board
+ Books and games for guest's enjoyment
+ Large, fully equipped chef's kitchen (see amenites) includes ice maker, Viking range, blender, crockpot, beverage center and wine chiller
+ Level two features a beverage refrigerator
Accommodations:
Suite 1 (second floor): Waterfront, King bed, ceiling fans, separate living room, wet bar area with beverage center and a workspace complete with desk and chair; private full bath with shower and double vanity sinks
Suite 2 (second floor): 2 separate bedrooms each with a queen bed; shared full bathroom in the middle has a tub shower combo
Suite 3 (second floor): Waterfront, king bed, shared waterside deck; private full bath with a tub shower combo
Suite 4 (second floor): Waterfront, queen bed, shared waterside deck; private full bath with original claw foot tub shower combo
Suite 5 (third floor): Waterfront, queen bed, living space, private deck and pullout sofa bed for additional sleeping space; private full bath with walk-in shower
Plus 2 additional bathrooms
Hair dryers are provided in each full bathroom
Dining Seating:
Kitchen island with seating for 4, morning table for 2, plus a formal dining room with seating for 6
for convenient access to refreshments
Outdoor Area:
Large, covered front porch with 2 chairs and coffee table
Multiple patios, decks and private balconies with several patio tables and plenty of seating, all lake-facing suites, offering breathtaking views
Gas grill
Parking for 2 vehicles in driveway
Plenty of nearby street and off-street parking available
Water Access:
Shelf rock shorefront
Water shoes recommended for swimming
Public dock use and water activity rentals available at nearby town marina
Extra Perks:
Walk across the street to Lakeshore Adventures for kayak, paddle board, etc rentals and to book zipline tours and charter fishing trips. Check-in instructions include details to get a discount when staying at Lakeside Legacy.
Amenity + damage protection waiver includes:
-Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels)
-A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom.
-PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).
Home Truths:
Security cameras are positioned at the front entrance and in the back of the house.
No dock
Until fiber optic is available in the area, we don’t want our guests to compete for streaming services and therefore just one Smart TV is provided.
No garage access.
14 maximum guests total on the property at all times. This home is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate bachelor or bachelorette parties, reunions, or other rowdy gatherings.
Door County Tourism Zone Commission Permit #02-56-2894-07
Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.
Perfectly situated in the heart of town with over 150 feet of lake frontage in your backyard. The large yard offers expansive views of Baileys Harbor, the lighthouse, and Lake Michigan. Enjoy three levels of patios and decks, all lake facing, to take in the incredible views. Plus, a classic, town facing covered front porch is the perfect spot to watch the folks walking by as they move around town. This heart of town location is steps from some of Door County’s finest dining, breweries, shops, marina, kayaking, charter fishing, and beaches.
Property Features:
+ 150 feet of Lake Michigan waterfront
+ Over 5000 square feet of living space!
+ One 65" Smart TV in main level living room, streaming content via Roku and equipped with a DVD player. Guests may log in using own account.
+ 4 spacious living spaces on the first level, offering versatile areas for relaxation and socializing
+ 2 dedicated work areas (parlor on the first level and primary suite on second level)
+ 3 fireplaces for aesthetics only, not for guest use
+ T-Mobile Home Internet service is available for reliable connectivity throughout your stay
+ Hot water heat throughout the home
+ Mitsubishi cooling appliances in each of the living spaces
+ Washer, dryer, iron, ironing Board
+ Books and games for guest's enjoyment
+ Large, fully equipped chef's kitchen (see amenites) includes ice maker, Viking range, blender, crockpot, beverage center and wine chiller
+ Level two features a beverage refrigerator
Accommodations:
Suite 1 (second floor): Waterfront, King bed, ceiling fans, separate living room, wet bar area with beverage center and a workspace complete with desk and chair; private full bath with shower and double vanity sinks
Suite 2 (second floor): 2 separate bedrooms each with a queen bed; shared full bathroom in the middle has a tub shower combo
Suite 3 (second floor): Waterfront, king bed, shared waterside deck; private full bath with a tub shower combo
Suite 4 (second floor): Waterfront, queen bed, shared waterside deck; private full bath with original claw foot tub shower combo
Suite 5 (third floor): Waterfront, queen bed, living space, private deck and pullout sofa bed for additional sleeping space; private full bath with walk-in shower
Plus 2 additional bathrooms
Hair dryers are provided in each full bathroom
Dining Seating:
Kitchen island with seating for 4, morning table for 2, plus a formal dining room with seating for 6
for convenient access to refreshments
Outdoor Area:
Large, covered front porch with 2 chairs and coffee table
Multiple patios, decks and private balconies with several patio tables and plenty of seating, all lake-facing suites, offering breathtaking views
Gas grill
Parking for 2 vehicles in driveway
Plenty of nearby street and off-street parking available
Water Access:
Shelf rock shorefront
Water shoes recommended for swimming
Public dock use and water activity rentals available at nearby town marina
Extra Perks:
Walk across the street to Lakeshore Adventures for kayak, paddle board, etc rentals and to book zipline tours and charter fishing trips. Check-in instructions include details to get a discount when staying at Lakeside Legacy.
Amenity + damage protection waiver includes:
-Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels)
-A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom.
-PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).
Home Truths:
Security cameras are positioned at the front entrance and in the back of the house.
No dock
Until fiber optic is available in the area, we don’t want our guests to compete for streaming services and therefore just one Smart TV is provided.
No garage access.
14 maximum guests total on the property at all times. This home is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate bachelor or bachelorette parties, reunions, or other rowdy gatherings.
Door County Tourism Zone Commission Permit #02-56-2894-07
Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.
Amenities at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery
Non-smoking
No pets allowed
Family friendly
Map of Baileys Harbor, WI
Ratings and reviews
10 / 10Outstanding·Oct 2025
Great property. Upon arrival, there were a few things we noticed. When contacted, the host responded timely to fix necessary items.
10 / 10Outstanding·Oct 2025
Fantastic time. Everything needed was provided. The only glitch was the oven which we dealt with. Location is awesome and the lawn setup made evenings wonderful. The house was very welcoming and gave us a great place to come back to after exploring the peninsula. 10/10 would stay here again.
8 / 10Excellent·Aug 2025
The space was big and plenty of rooms and bathrooms. Location was amazing. Right next to a beach for the kids and playground. Coffee shop across the street, very walkable. Big kitchen to cook in and eat with family.No beach towels and the shampoo/body wash and other house hold stuff was small or only provided a limited amount so we had to end up buying stuff (laundry soap) or ran out of (dishwasher pods)Overall, it was a great memorable stay. Beautiful views with plenty of room for kids to run around and be entertained.
6 / 10Average·Sep 2024
The property was rented to accommodate 14 people for 5 days and 4 nights. With that in mind we needed more linens and towels which we had to ask for and got once. There were no linens for the roll out couch which we took a top sheets off a bed for a sheet and blanket. there were no light bulbs in many of the lamps, ice maker was broke, air conditioners were not working ( fuse blew), found garbage, clothes and toys in couches and closets, washer stunk, not enough chairs or tables to sit outside as a group or lighting (to enjoy the lake, moon and stars), coffee pot was nasty and had to sterilize. The door next to the garage in front slams if not held and cut/bruised one of the renters. no storage to put our food so we occupied the island and table with food. Most of the downfalls were brought up to the person who was there to fix stuff so we would not get blamed or charged. For the money we paid I would not stay there again. The Jack and Jill bathroom/bedroom was weird, some even got locked in that bathroom until heard. Thank you, and hope this helps to get your place up to what is advertised.
$$$$
Top rated by guests
9.6Outstanding
(19 Ratings)
"Great property. Upon arrival, there were a few things we noticed. When contacted, the host responded timely to fix necessary items."
Amanda M.Don't miss out! Price and availability may change
