Entire home

Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor

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Exterior - Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor (Baileys Harbor)
Outdoor dining - Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor (Baileys Harbor)
Exterior - Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor (Baileys Harbor)
6 bedrooms, iron/ironing board, free WiFi, bed sheets - Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor (Baileys Harbor)
Dining - Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor (Baileys Harbor)
Experience the perfect blend of lakeside charm and modern comfort at Lakeside Legacy. Located in the heart of Baileys Harbor, this lovingly cared for home offers expansive views of Lake Michigan from three levels of patios and decks, a classic covered front porch to watch the town bustle by, and 150 feet of lake frontage with shelf rock shorefront.

Reviews

9.6 out of 10
Exceptional

Entire home

6 bedrooms7 bathroomsSleeps 14511 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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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).

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 7 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • DVD player
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • On the waterfront

Things to do

  • Cycling nearby
  • Fishing nearby
  • Hiking/biking trails nearby

Safety features

  • 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)
  • Fire extinguisher

General

  • Garden
  • Unit size: 5,500 square feet

Similar properties

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

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

We should mention

A car is recommended for transport to and from this property

About the area

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. Water tubing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking nearby. Visit our Baileys Harbor travel guide
View more Holiday homes in Baileys Harbor
Map
Baileys Harbor, WI

What's nearby

  • Door County Brewing Company
    Door County Brewing Company
    8 min walk - 0.7 km
  • Building at the Ridges Sanctuary nature preserve in Baileys Harbor, Wisconsin
    Ridges Sanctuary
    16 min walk - 1.4 km
  • Cana Island Lighthouse
    Cana Island Lighthouse
    13 min drive - 11.6 km
  • Baileys Harbor Ridges Park
    11 min walk - 1.0 km
  • Anclam Beach Park
    11 min walk - 1.0 km

Restaurants

  • AC Tap
    6 min drive
  • Coyote Roadhouse
    5 min drive
  • Stone's Throw Winery
    9 min drive
  • Sway Brewing + Blending
    6 min walk
  • Cornerstone Pub
    2 min walk

Frequently asked questions

Is Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery pet-friendly?

No, pets are not allowed at this property.

How much is parking at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?

On-site parking is available at the property.

What time is check-in at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?

Check-in begins at 4:00 PM.

What time is check-out at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?

Checkout is at 10:00 AM.

Where is Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery 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.

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Our Lakeside Legacy - Expansive Retreat in Downtown Baileys Harbor Reviews

Reviews

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.
More informationOpens in a new window
Rating 10 - Excellent. 15 out of 19 reviews
Rating 8 - Good. 3 out of 19 reviews
Rating 6 - Okay. 1 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.0

Cleanliness

10

Location

10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Christiane M.

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
Verified

10/10 Excellent

Craig K.

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
Verified

10/10 Excellent

Candi S.

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
Verified

10/10 Excellent

Kimberly O.

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
Verified

10/10 Excellent

Maya A.

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
Verified

10/10 Excellent

Jackie O.

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
Verified

6/10 Okay

Tonia F.

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
Verified

10/10 Excellent

Austin

Liked: Cleanliness, amenities, property conditions & facilities, communication
Responsive owner, beautiful property.
Stayed 5 nights in Jul 2025
Verified

10/10 Excellent

Paula C.

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
Verified

10/10 Excellent

Amanda M.

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
Verified

8/10 Good

Ellen P.

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
Verified

10/10 Excellent

Vanessa S.

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
Verified

10/10 Excellent

Jim F.

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
Verified

10/10 Excellent

Lisa S.

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
Verified

8/10 Good

Russ P.

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
Verified

10/10 Excellent

Nick V.

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

Awesome lake house

Great experience in Bailey's Harbor
Stayed 3 nights in Aug 2023
Verified

8/10 Good

Brittany D.

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
Verified

10/10 Excellent

Cathy B.

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

10/10 Excellent

Brad P.

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