Heart of Baileys Harbor.Within a 10-minute walk of the vacation home, you'll find Door County Brewing Company and Baileys Harbor Ridges Park. Lake Michigan and Anclam Beach Park are also within half a mile (1 km).
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
General
Garden
Unit size: 5,500 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events 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
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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.
Property is also known as
130
Frequently asked questions
Does Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery to the beach?
This vacation home is a short 10-minute walk from Anclam Beach Park and 8.3 mi (16-min drive) from Fish Creek Public Beach. Don't forget your sunscreen!
Does Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?
No, there is no casino at this vacation home.
What time is check-in at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?
Check-in begins at 4:00 PM.
Is there free parking at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?
Free parking is not available at this vacation home.
Does Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery have a pool?
This vacation home does not have a pool.
Does Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery have a spa?
There are no spa services available at this vacation home.
How close is Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery to downtown Baileys Harbor?
This vacation home is 0.1 mi away from Baileys Harbor.
Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery Reviews
Reviews
9.6
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 15 out of 19 reviews
10 - Excellent
15
Rating 8 - Good. 3 out of 19 reviews
8 - Good
3
Rating 6 - Okay. 1 out of 19 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 19 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 19 reviews
2 - Terrible
0
9.0/10
Cleanliness
10/10
Amenities
10/10
Property conditions & facilities
Reviews
10/10 Excellent
Amanda M.
Oct 14, 2025
Liked: Cleanliness
Great property. Upon arrival, there were a few things we noticed. When contacted, the host responded timely to fix necessary items.
Amanda M.
Stayed 2 nights in Oct 2025
10/10 Excellent
Craig K.
Oct 9, 2025
Liked: Cleanliness
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.
Craig K.
Stayed 5 nights in Sep 2025
10/10 Excellent
Cathy B.
Aug 30, 2025
Liked: Cleanliness
Cathy B.
Stayed 2 nights in Sep 2024
8/10 Good
Brittany D.
Aug 29, 2025
Liked: Cleanliness
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.
Brittany D.
Stayed 4 nights in Aug 2025
8/10 Good
Ellen P.
Aug 22, 2025
The property is the perfect location. The check in and out were no problem. Could of been cleaner.
Ellen P.
Stayed 7 nights in Aug 2025
10/10 Excellent
Paula C.
Aug 5, 2025
Liked: Cleanliness
Late summer road trip
The property had an amazing location and the views were exquisite. We had a wonderful time.
Paula C.
Stayed 3 nights in Jul 2025
10/10 Excellent
Jim F.
Jul 19, 2025
Perfect Lake Views and Ideal Location
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!
Beautiful home, great location for anywhere in Door County.
Lisa S.
Stayed 5 nights in Aug 2024
6/10 Okay
Tonia F.
Sep 2, 2024
Lakeside Legacy
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.
Tonia F.
Stayed 4 nights in Aug 2024
10/10 Excellent
Vanessa S.
Aug 4, 2024
Liked: Cleanliness
Family Vacation
Beautiful home. Great vacation and would definitely stay again.
Vanessa S.
Stayed 7 nights in Jul 2024
8/10 Good
Russ P., Indianapolis
Aug 1, 2024
Liked: Cleanliness
beautiful location
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.
Russ P.
Stayed 5 nights in Jul 2024
10/10 Excellent
Kimberly O.
Jul 28, 2024
Liked: Cleanliness
Gorgeous waterfront property
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!!
Kimberly O.
Stayed 4 nights in Jul 2024
10/10 Excellent
Candi S.
May 11, 2024
Liked: Cleanliness
Great house, great location!
This house is gorgeous and is about 12 minutes to everything. A few bars/wineries in walking distance. House had everything we needed and it was very comfortable. Definitely someplace we would stay again.
Candi S.
Stayed 4 nights in May 2024
10/10 Excellent
Christiane M.
Oct 22, 2023
Liked: Cleanliness
Great family get together location
The property is beautiful, conveniently located and with amazing indoor and outdoor space
Christiane M.
Stayed 2 nights in Oct 2023
10/10 Excellent
Jackie O.
Sep 4, 2023
Liked: Cleanliness
Lakeside loveliness!
The house was picture perfect for our extended family vacation! Being right on the water was spectacular. We found the house to be stocked with most of the items we have come to expect from renting other properties. There was no hair dryer. We found the beds and linens to be soft and comfortable.
One thing that was a bit of a surprise was the layout of the two bedrooms with the shared bath. While reading the description, we did not understand that you had to walk through the first bedroom and bathroom to get to that second bedroom. It worked for us, but may not be ideal for all groups. Maybe I missread, but wanted to point it out to others.
As a previous reviewer mentioned, we also had a problem with hot water and multipe showers going at once.
Jackie O.
Stayed 3 nights in Sep 2023
10/10 Excellent
Nick V.
Aug 19, 2023
Liked: Cleanliness
Awesome lake house
Great experience in Bailey's Harbor
Nick V.
Stayed 3 nights in Aug 2023
10/10 Excellent
Maya A.
Aug 6, 2023
Liked: Cleanliness
Great home base for a trip to Door County
Located in Bailey’s Harbor so everything is within a 15 min driving distance - the view is beautiful so even if you wanted to linger at the house and stare out at the water all day you could. Our family enjoyed eating in the spacious kitchen for breakfast each morning, while most days we spent afternoons out. The grill was a little dirty from continuous use - so we needed to clean it to be able to grill on it. The fat trap needs to be emptied to ensure that there is not a hazard from flames shooting up. And the only other issue is the showers and not being able to have multiple people showering at the same time. If you’re booking a large house and expect a number of people to stay and use the numerous bathrooms at once, the distribution of the hot water needs to be remedied. Otherwise the house was ideal for our needs.