Guests love the walkable location for its easy access on foot.
Discover nearby landmarks
Walk to Door County Brewing Company
6 bedrooms7 bathroomsSleeps 14
Popular amenities
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Balcony
Free Wi-Fi
Explore the area
Baileys Harbor, WI
Door County Brewing Company
Place, Door County Brewing Company
8 min walk
Baileys Harbor Ridges Park
Place, Baileys Harbor Ridges Park
11 min walk
Anclam Beach Park
Place, Anclam Beach Park
11 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).
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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
Safety features at this property include a fire extinguisher
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
About the area
Baileys Harbor
Located in Baileys Harbor, this holiday home is in the city centre and on the waterfront. Cana Island Lighthouse is a notable landmark, 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 nearby fishing, or enjoy the great outdoors with cycling.
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 25 June 2026, prices found for a 1-night stay for 2 adults at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor on 14 September 2026 start from NZ$3,020, 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 at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor?
On-site 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?
Checkout 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 holiday 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.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The property had an amazing location and the views were exquisite. We had a wonderful time.
Paula C.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 13 August 2025
Hello Paula,
Thank you for sharing your experience! We’re so happy you had an amazing stay and look forward to welcoming you back.
Warm regards,
The Simple Life Rentals Team
Beautiful home. Great vacation and would definitely stay again.
Vanessa S.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 21 August 2024
Thank you for the lovely review! We are delighted to hear that you had a wonderful vacation and enjoyed your stay. We look forward to welcoming you back in the future!
Verified
8/10 Good
Ellen P.
22 August 2025
Liked: Check-in, location
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
Response from VrboOwner on 2 September 2025
Happy to hear the location worked out perfectly and that check-in/check-out went smoothly! We’re sorry the cleaning could have been better, we’ll work on it. Hope to host you again!
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
Response from VrboOwner on 15 October 2025
Hello Amanda,
Thank you very much for taking the time to share your feedback and review! We truly appreciate your understanding and patience, and we’re glad our team was able to assist promptly during your stay. We hope to have the opportunity to welcome you back for an even smoother experience next time!
Warm regards,
The Simple Life Rentals Team
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
Response from VrboOwner on 9 October 2025
Hello Craig,
We truly appreciate your kind words and are so glad to hear you had a fantastic stay! It’s wonderful to know the home, location, and outdoor space made your visit enjoyable. Thank you for being understanding about the oven issue. We’d be delighted to welcome you back again anytime!
Warm regards,
The Simple Life Rentals Team
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!
Jim F.
Stayed 6 nights in Jul 2025
Response from VrboOwner on 29 July 2025
We love hearing this, thank you! So glad you enjoyed the views, the porch, and the location. It was a pleasure hosting you. Come back anytime!
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
Response from VrboOwner on 13 May 2024
Thank you, thank you!! These genuine reviews and your happy experience in one of our homes is why we do what we do. We hope to host you again soon, Candi!
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
Response from VrboOwner on 9 September 2025
Thank you for sharing your experience! We’re glad you enjoyed the location, views, and family-friendly amenities. We do apologize about the beach towels, we note in the listing that guests should bring their own, but we truly appreciate your feedback and suggestion. Regarding household supplies, our starter pack is just to help guests get settled in, and we send details a week before check-in so guests can plan ahead. Overall, we’re so happy to hear your stay was memorable, and we’d love to host you again!
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
Response from VrboOwner on 8 August 2024
We are so grateful for your kind review, Kim! This means so much to our team and to the home owners. Happy to hear you had a wonderful stay and we hope to host you again!
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.
Maya A.
Stayed 3 nights in Jul 2023
Response from VrboOwner on 11 August 2023
We appreciate all your feedback, Maya. Thank you! So glad that you had a great overall stay.
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
Response from VrboOwner on 25 September 2023
Thank you for sharing your feedback with us! We are pleased to hear you and your family had a great overall stay, and hope we may host you again sometime.
Verified
6/10 Okay
Tonia F.
2 September 2024
Liked: Check-in, location
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
Response from VrboOwner on 10 September 2024
Thank you for your detailed feedback, Tonia. Your comments are valuable to us, and we are reviewing these concerns to ensure a better experience for future guests. We will review and improve to match the standards we aim to provide for all guests that love this beautiful, lakeside home.
This is a large house with multiple gathering areas and a wonderful kitchen. Perfect for multiple couples traveling together. The backyard offers a beautiful water view and plenty of seating. Watch the birds dive bomb for fish or the rabbits scurry around the yard. Lots to do within a short drive, or walk to some of Baileys Harbor businesses.