Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor

Photo gallery for Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor

A bedroom with a wooden headboard, a wooden wardrobe, and a view of a balcony with a railing and a body of water.
A dining area with a table, chairs, a bookshelf, and a view of a body of water.
A spacious living area with a large window overlooking a body of water, wooden walls, and a cozy seating arrangement.
A wooden-paneled room with a sofa, ottoman, and 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

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Lake Michigan

Popular amenities

  • Balcony
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Internet
  • Onsite parking available

Explore the area

View 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

Add dates for prices

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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. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling.
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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
  • Peninsula State Park - 13 min drive - 15.2 km

Restaurants

  • ‪AC Tap - ‬6 min drive
  • ‪Sway Brewing + Blending - ‬6 min walk
  • ‪Coyote Roadhouse - ‬5 min drive
  • ‪Roost + Banter - ‬1 min walk
  • ‪Blue Ox - ‬4 min walk

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 15 Nov 2026, prices found for a 1-night stay for 2 adults at Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor on 17 May 2027 start from AU$7,276, 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

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 18 out of 24 reviews
Rating 8 - Good. 4 out of 24 reviews
Rating 6 - Okay. 2 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

8.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.2/10

Communication

10/10

Location

9.2/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and very accommodating to a larger group. There are minor upgrades and/or maintenance issues that could be performed that would make the property rate even higher, but all in all we found the home to fit our needs quite well.
Stayed 4 nights in Sep 2026
Response from VrboOwner on 5 Oct 2026
Hello Ron, Thank you so much for your kind review! We’re glad to hear that Our Lakeside Legacy was a comfortable fit for your group and that you enjoyed the location. We appreciate you taking the time to share your experience with us and would love to welcome you back for another Door County stay! Warm regards, The Simple Life Rentals Team
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location and view are absolutely perfect. If you are strictly on vacation it’s a great house. If you have a wedding or event, be aware the bathrooms and lighting are a challenge. Hosts are very responsive. Also understand that one of the bedrooms can only be entered through another bedroom. It was overall a comfortable home for our group.
Stayed 3 nights in Sep 2026
Response from Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor on 9 Oct 2026
Hello Sharon, Thank you so much for sharing your review! We’re glad you enjoyed the beautiful lake views and found the home comfortable for your group. We also appreciate you highlighting the areas that could be challenging, especially for guests attending a wedding or special event. We’ll share your comments with our team as we continue looking for ways to improve the guest experience. We hope to have the opportunity to welcome you back for an even better stay! Warm regards, The Simple Life Rentals Team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Jun 2026
Response from VrboOwner on 28 Aug 2026
Thank you, Lois, for your wonderful feedback. I'm thrilled to hear you enjoyed the spaciousness and beautiful surroundings of our property. We look forward to welcoming you back for another memorable stay! Warm regards, The Simple Life Rentals Team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family get together location

The property is beautiful, conveniently located and with amazing indoor and outdoor space
Stayed 2 nights in Oct 2023
Response from VrboOwner on 6 Nov 2023
Thank you, Christiane! Your kind feedback means so much to our owners and team.
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Responsive owner, beautiful property.
Stayed 5 nights in Jul 2025
Response from Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery on 9 July 2025
Thanks so much, we’re happy you had a great experience! 😊
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Beautiful home. Great vacation and would definitely stay again.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 21 Aug 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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Late summer road trip

The property had an amazing location and the views were exquisite. We had a wonderful time.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 13 Aug 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family getaway

Beautiful home, great location for anywhere in Door County.
Stayed 5 nights in Aug 2024
Response from VrboOwner on 10 Sept 2024
Thank you for your kind review, Lisa! Our team and the homeowners are thrilled you enjoyed your stay. We hope you will consider staying with us again.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 5 nights in Jul 2024
Response from VrboOwner on 2 Aug 2024
Thank you for your review and we are grateful to hear you and your group enjoyed your stay. The waterfront and downtown location cannot be beat!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome lake house

Great experience in Bailey's Harbor
Stayed 3 nights in Aug 2023
Response from VrboOwner on 28 Aug 2023
Thank you, Nick! We hope to host you again sometime.
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy

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!
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!
Verified review

8/10 Good

Liked: Check-in, location
The property is the perfect location. The check in and out were no problem. Could of been cleaner.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 2 Sept 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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property. Upon arrival, there were a few things we noticed. When contacted, the host responded timely to fix necessary items.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 15 Oct 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Sep 2025
Response from VrboOwner on 9 Oct 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!!
Stayed 4 nights in Jul 2024
Response from VrboOwner on 8 Aug 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!
Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy
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.
Stayed 4 nights in Aug 2025
Response from VrboOwner on 9 Sept 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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 3 nights in Jul 2023
Response from VrboOwner on 11 Aug 2023
We appreciate all your feedback, Maya. Thank you! So glad that you had a great overall stay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 3 nights in Sep 2023
Response from VrboOwner on 25 Sept 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 review

6/10 Okay

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.
Stayed 4 nights in Aug 2024
Response from VrboOwner on 10 Sept 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.
Verified review

10/10 Excellent

Stayed 3 nights in Aug 2026
Verified review

6/10 Okay

Liked: Check-in, listing accuracy
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Sep 2024
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