Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery

Baileys Harbor, Wisconsin
$1894 avg/night Minimum Stay 2 Nights
Bed 6

Bed

Bath 7

Bath

Home Private Vacation Home

Property Type

Sleep 14

Max Sleeps

Night 2 nights

Min Stay

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 oftown 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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 5500 Sq Ft (511 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • BATHROOMS

    7 Bathrooms Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Marina Nearby Sailing Nearby Swimming Nearby Water Tubing Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Books DVD Player Games Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Heating
  • LOCATION HIGHLIGHTS

    In The City Center On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Limited Housekeeping
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 14

Map Map

School District Rates & Availability

Review Review

  • Austin

    Submitted Jul 7, 2025

    Stayed Jul 2, 2025

    Responsive owner, beautiful property.

  • Amanda M.

    Submitted Oct 14, 2025

    Stayed Oct 2, 2025

    Great property. Upon arrival, there were a few things we noticed. When contacted, the host responded timely to fix necessary items.

  • Craig K.

    Submitted Oct 9, 2025

    Stayed Sep 24, 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.

  • Brittany D.

    Submitted Aug 29, 2025

    Stayed Aug 25, 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.

  • Ellen P.

    Submitted Aug 22, 2025

    Stayed Aug 15, 2025

    The property is the perfect location. The check in and out were no problem. Could of been cleaner.

  • Paula C.

    Submitted Aug 5, 2025

    Stayed Jul 31, 2025

    The property had an amazing location and the views were exquisite. We had a wonderful time.

  • Jim F.

    Submitted Jul 19, 2025

    Stayed Jul 13, 2025

    We had a fantastic stay! The house had amazing views of the lake and a perfect porch for relaxing and people watching. The location couldn’t have been better—walking distance to great breweries, restaurants, and everything in town. We had a couple of quick questions during our stay, and the host’s communication was prompt and helpful. Highly recommend!

  • Lisa S.

    Submitted Sep 5, 2024

    Stayed Aug 25, 2024

    Beautiful home, great location for anywhere in Door County.

  • Tonia F.

    Submitted Sep 2, 2024

    Stayed Aug 21, 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.

  • Vanessa S.

    Submitted Aug 4, 2024

    Stayed Jul 28, 2024

    Beautiful home. Great vacation and would definitely stay again.

  • Russ P.

    Submitted Aug 1, 2024

    Stayed Jul 14, 2024

    The house has a beautiful location right on the water. It is in town and convenient to walk to businesses in Bailey's Harbor. We enjoyed the stay.

  • Kimberly O.

    Submitted Jul 28, 2024

    Stayed Jul 24, 2024

    We really enjoyed staying at this house. It was large enough for our group of 7 to spread out. The house is a combination of historic and contemporary decor. It has a lot of history with a stunning view of the water. The location was perfect, we walked to nearby restaurants every night. Highly recommend!!

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Total

Includes taxes and fees
$1,894+
View details