Entire home
Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery
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Reviews
9.6 out of 10
Exceptional
6 bedrooms 7 bathrooms Sleeps 14 511.0 sq m
Popular amenities
Explore the area

Baileys Harbor, WI
- Door County Brewing Company7 min walk
- Kangaroo Lake5 min drive
- Cana Island Lighthouse16 min drive
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
Bathroom 2
Bathroom 3
Bathroom 4
Bathroom 5
Bathroom 6
Bathroom 7
Spaces
Deck or patio
Balcony
Garden
Dining area
About this property
Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery
Welcome to our 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. 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. Lakeside Legacy is the best of both worlds with the hustle and bustle out to the front of the home and the tranquility of wildlife and waves in your backyard. This heart of town location is steps from some of Door County’s finest dining, breweries, shops, marina, kayaking, charter fishing, and beaches.
Experience the perfect blend of lakeside charm and modern comfort at our Baileys Harbor retreat. Book now to secure your unforgettable vacation at our Lakeside Legacy.
*Due to the nature of the home and proximity of neighbors this property is geared for family vacations or getaways. We cannot accommodate reunions, weddings, bachelor or bachelorette parties or any other events that exceed the maximum number of guests as noted below.
Door County Tourism Zone Commission Permit #02-56-2894-07
About the space:
14 maximum guests total on the property at all times
Boasting over 5000 square feet of living space – ensuring ample space for everyone to relax and unwind
6 bedrooms / 7 bathrooms
No pets allowed
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. (Until fiber optic is available in the area, we don’t want our guests to compete for streaming services and therefore currently just one Smart TV is provided)
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 and not for guest use
T-Mobile Home Internet service is available for reliable connectivity throughout your stay
Hot water heat for cozy warmth during cooler seasons
Mitsubishi cooling appliances in each of the living spaces for comfortable indoor temperatures
Washer and dryer
Books and games for guest's enjoyment
Accommodations:
Suite 1 (second floor): Waterfront, King bed, shower, double vanity sinks, ceiling fans, separate living room, wet bar area with beverage center and a workspace complete with desk and chair
Suite 2 (second floor): 2 separate bedrooms both featuring a queen bed with shared bathroom in the middle featuring a tub/shower combination in bath
Suite 3 (second floor): Waterfront, king bed, tub/shower combination in bath, shared waterside deck
Suite 4 (second floor): Waterfront, queen bed, original claw foot tub with shower combination, shared waterside deck
Suite 5 (third floor): Waterfront, queen bed, shower only in bath, separate living space, private deck and pullout sofa bed for additional sleeping space
Plus 2 additional bathrooms
Kitchen Amenities:
The large, chef’s kitchen is equipped with a refrigerator, freezer, ice maker, dishwasher, microwave, Viking range, oven, blender, toaster, beverage center and wine chiller
A Keurig and tea kettle are provided
Dishes, glassware, utensils, pots, pans, baking sheets, kitchen towels, hot pads, a crockpot, grill utensils and wine glasses and baking sheets are also at the property
Kitchen island with seating for 4, morning table for 2, plus a formal dining room with seating for 6
Level two features a beverage refrigerator 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 for delightful outdoor grilling experiences
Parking for 2 vehicles in driveway
Plenty of nearby street and off-street parking available
No garage access provided
Water Access:
150 feet of Lake Michigan waterfront
Shelf rock shorefront
Water shoes recommended for swimming
Public dock use and water activity rentals available at nearby town marina
No dock installed at property
Walk across the street to Lakeshore Adventures for kayak, paddle board rentals, and more
Provided:
• Bed linens, pillows, blankets, and bathroom towels are provided. Please bring your own beach towels.
• We do provide a starter pack of essentials which includes the following: 2 rolls of toilet paper per bathroom, 2 rolls of paper towels, dish soap, dishwasher soap, hand soap and 2-3 garbage bags.
• We also supply one each of travel size shampoo, conditioner and bodywash per full bathroom.
• Due to health and safety guidelines made by the health department, all pantry items must be removed between guests. Please bring cooking essentials you might need such as cooking oil/spray, salt, pepper and other spices, sugar, etc.
Surrounding Area:
Door County is full of many amazing things to see and do! We recommend that you check out Destination Door County, and the visitor's bureau online, to help map out your vacation. "Door County Vacationers" is also a great FB group to join to get recommendations on everything from favorite restaurants to favorite tours, places to rent boats, and things to do.
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.
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. Lakeside Legacy is the best of both worlds with the hustle and bustle out to the front of the home and the tranquility of wildlife and waves in your backyard. This heart of town location is steps from some of Door County’s finest dining, breweries, shops, marina, kayaking, charter fishing, and beaches.
Experience the perfect blend of lakeside charm and modern comfort at our Baileys Harbor retreat. Book now to secure your unforgettable vacation at our Lakeside Legacy.
*Due to the nature of the home and proximity of neighbors this property is geared for family vacations or getaways. We cannot accommodate reunions, weddings, bachelor or bachelorette parties or any other events that exceed the maximum number of guests as noted below.
Door County Tourism Zone Commission Permit #02-56-2894-07
About the space:
14 maximum guests total on the property at all times
Boasting over 5000 square feet of living space – ensuring ample space for everyone to relax and unwind
6 bedrooms / 7 bathrooms
No pets allowed
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. (Until fiber optic is available in the area, we don’t want our guests to compete for streaming services and therefore currently just one Smart TV is provided)
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 and not for guest use
T-Mobile Home Internet service is available for reliable connectivity throughout your stay
Hot water heat for cozy warmth during cooler seasons
Mitsubishi cooling appliances in each of the living spaces for comfortable indoor temperatures
Washer and dryer
Books and games for guest's enjoyment
Accommodations:
Suite 1 (second floor): Waterfront, King bed, shower, double vanity sinks, ceiling fans, separate living room, wet bar area with beverage center and a workspace complete with desk and chair
Suite 2 (second floor): 2 separate bedrooms both featuring a queen bed with shared bathroom in the middle featuring a tub/shower combination in bath
Suite 3 (second floor): Waterfront, king bed, tub/shower combination in bath, shared waterside deck
Suite 4 (second floor): Waterfront, queen bed, original claw foot tub with shower combination, shared waterside deck
Suite 5 (third floor): Waterfront, queen bed, shower only in bath, separate living space, private deck and pullout sofa bed for additional sleeping space
Plus 2 additional bathrooms
Kitchen Amenities:
The large, chef’s kitchen is equipped with a refrigerator, freezer, ice maker, dishwasher, microwave, Viking range, oven, blender, toaster, beverage center and wine chiller
A Keurig and tea kettle are provided
Dishes, glassware, utensils, pots, pans, baking sheets, kitchen towels, hot pads, a crockpot, grill utensils and wine glasses and baking sheets are also at the property
Kitchen island with seating for 4, morning table for 2, plus a formal dining room with seating for 6
Level two features a beverage refrigerator 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 for delightful outdoor grilling experiences
Parking for 2 vehicles in driveway
Plenty of nearby street and off-street parking available
No garage access provided
Water Access:
150 feet of Lake Michigan waterfront
Shelf rock shorefront
Water shoes recommended for swimming
Public dock use and water activity rentals available at nearby town marina
No dock installed at property
Walk across the street to Lakeshore Adventures for kayak, paddle board rentals, and more
Provided:
• Bed linens, pillows, blankets, and bathroom towels are provided. Please bring your own beach towels.
• We do provide a starter pack of essentials which includes the following: 2 rolls of toilet paper per bathroom, 2 rolls of paper towels, dish soap, dishwasher soap, hand soap and 2-3 garbage bags.
• We also supply one each of travel size shampoo, conditioner and bodywash per full bathroom.
• Due to health and safety guidelines made by the health department, all pantry items must be removed between guests. Please bring cooking essentials you might need such as cooking oil/spray, salt, pepper and other spices, sugar, etc.
Surrounding Area:
Door County is full of many amazing things to see and do! We recommend that you check out Destination Door County, and the visitor's bureau online, to help map out your vacation. "Door County Vacationers" is also a great FB group to join to get recommendations on everything from favorite restaurants to favorite tours, places to rent boats, and things to do.
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.
Add dates for prices
Amenities
Washing machine
Dryer
Free WiFi
Outdoor space
Parking available
Water view
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
We should mention
A car is recommended for transport to and from this property
About the area
Baileys Harbor
Located in Baileys Harbor, this holiday home is in the city centre 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. Water tubing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and hunting nearby.

Baileys Harbor, WI
What's nearby
- Door County Brewing Company - 7 min walk - 0.6 km
- Baileys Harbor Ridges Park - 13 min walk - 1.1 km
- Ridges Sanctuary - 16 min walk - 1.4 km
- Kangaroo Lake - 5 min drive - 4.7 km
- Cana Island Lighthouse - 16 min drive - 10.8 km
Restaurants
- AC Tap - 6 min drive
- Cornerstone Pub - 2 min walk
- Sway Brewing + Blending - 6 min walk
- Coyote Roadhouse - 5 min drive
- Door County Brewing Company - 1 min walk
Frequently asked questions
About the host
Hosted by The Simple Life Hospitality

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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