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Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor

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A bedroom with a wooden headboard, a wooden wardrobe, and a view of a balcony with a railing and a body of water.
A wooden-paneled room with a sofa, ottoman, and TV.
A dining area with a table, chairs, a bookshelf, and a view of a body of water.
Third first floor living space includes 65" Smart TV
A spacious kitchen with wooden cabinets, a central island, and large windows offering a view of the water.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Door County Brewing Company
6 bedrooms7 bathroomsSleeps 14

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Balcony
  • Free WiFi

Explore the area

View in a map
Baileys Harbor, WI
  • Place, Door County Brewing Company
    ‪8 min walk‬
  • Place, Baileys Harbor Ridges Park
    ‪11 min walk‬
  • Place, Ridges Sanctuary
    ‪16 min walk‬

Rooms & beds

6 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 King Bed

Bedroom 5

1 Queen Bed

Bedroom 6

1 Queen Bed and 1 Double Sofa Bed

7 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Bathroom 7

Toilet · Shower only

Spaces

Kitchen
Office
Balcony
Garden

About this property

Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor

Summary:

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.



The Space:

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



Door County Tourism Zone Commission Permit #02-56-2894-07



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.



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.



Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.



Other Things to Note:

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).
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3440536
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Baileys Harbor

Located in Baileys Harbor, this vacation home is in the city center and on the waterfront. Cana Island Lighthouse and The Skyway Drive-In Theatre are local landmarks, and the area's natural beauty can be seen at Lake Michigan and Peninsula State Park. Looking to enjoy an event or a game while in town? See what's going on at Peg Egan Performing Arts Center, or consider a night out at Woodwalk Gallery. Discover the area's water adventures with fishing nearby, or enjoy the great outdoors with cycling.
Map
Baileys Harbor, WI

What's nearby

  • Door County Brewing Company - 8 min walk - 0.7 km
  • Baileys Harbor Ridges Park - 11 min walk - 1.0 km
  • Anclam Beach Park - 11 min walk - 1.0 km
  • Ridges Sanctuary - 16 min walk - 1.4 km
  • Cana Island Lighthouse - 13 min drive - 11.6 km

Restaurants

  • ‪AC Tap - ‬6 min drive
  • ‪Cornerstone Pub - ‬2 min walk
  • ‪Harbor Fish Market & Grille - ‬2 min walk
  • ‪Stone's Throw Winery - ‬9 min drive
  • ‪Koepsel's Farm Market - ‬8 min drive

Frequently asked questions

Is Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor?

As of Aug 24, 2026, prices found for a 1-night stay for 2 adults at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor on Aug 30, 2026 start from $1,537, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor?

Check-in begins at 4:00 PM.

What time is check-out at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor?

Check-out is at 10:00 AM.

Where is Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor located?

Located in the heart of Baileys Harbor, this vacation home is within 1 mi (2 km) of Door County Brewing Company and Lake Michigan. Baileys Harbor Ridges Park and Anclam Beach Park are also within 10 minutes.

About the host

Hosted by The Simple Life Hospitality

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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