Entire home

Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery

Waterfront vacation home in Baileys Harbor with balcony

Choose dates to view prices

Photo gallery for Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery

Dining
Interior
Smart TV, DVD player, books
Smart TV, DVD player, books
6 bedrooms, iron/ironing board, free WiFi, bed sheets

Reviews

9.6 out of 10
Exceptional

Entire home

6 bedrooms7 bathroomsSleeps 145500 sq ft

Popular amenities

  • Washer
  • Dryer
  • Free WiFi
  • Outdoor Space
  • Parking available
  • Barbecue grill

Explore the area

View in a map
Baileys Harbor, WI
  • Place, Door County Brewing Company
    ‪7 min walk‬
  • Place, Baileys Harbor Ridges Park
    ‪11 min walk‬
  • Place, Ridges Sanctuary
    ‪16 min walk‬

Room options

About the neighborhood

Baileys Harbor

This vacation home places you next to Lake Michigan and within a 10-minute walk of Door County Brewing Company. The vacation home includes a balcony, a sofa bed, and a microwave.

What's nearby

  • Door County Brewing Company - 7 min walk - 0.4 miles
  • Baileys Harbor Ridges Park - 11 min walk - 0.6 miles
  • Anclam Beach Park - 11 min walk - 0.6 miles
  • Ridges Sanctuary - 16 min walk - 0.9 miles
  • Cana Island Lighthouse - 13 min drive - 6.8 miles

Restaurants

  • ‪Coyote Roadhouse - ‬5 min drive
  • ‪Sway Brewing + Blending - ‬6 min walk
  • ‪Cornerstone Pub - ‬2 min walk
  • ‪Door County Brewing Company - ‬1 min walk
  • ‪AC Tap - ‬6 min drive

About this property

Entire place

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 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.

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

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.

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).

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.

Door County Tourism Zone Commission Permit #02-56-2894-07

Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.
The vacation home is heated and features a balcony and 7 bathrooms, and there's space to spread out with 6 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a sofa bed, and a microwave. Limited housekeeping is available.

Similar properties

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car required
  • Parking on site

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 7 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping

Location highlights

  • In a village
  • In the city center
  • Near the marina
  • On the waterfront

Things to do

  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Swimming nearby
  • Water tubing nearby
  • Windsurfing nearby
  • Winery tours 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)

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Property is also known as

130

Frequently asked questions

What is there to do around this vacation home?

Located steps from Lake Michigan, this vacation home is in Baileys Harbor, and within a 10-minute walk of Door County Brewing Company and Baileys Harbor Ridges Park. You'll also find Ridges Sanctuary and Anclam Beach Park less than a mile away.

Will I be able to park at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What do couples enjoy most about Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?

At this waterfront vacation home, amenities that appeal to couples include a smart TV, water views in some accommodations, as well as a garden.

Does Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery have a hot tub?

No, there isn't a spa tub at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, there aren't connecting rooms at this vacation home.

Can I book a room with a balcony at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery?

Yes, every accommodation at Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery comes with a balcony with some featuring water views.

Charming Retreat in Downtown Baileys Harbor Across from Door County Brewery Reviews

Reviews

9.6

Exceptional

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

9.0/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

Reviews

10/10 Excellent

Amanda M.

Liked: Cleanliness
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

10/10 Excellent

Craig K.

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.
Stayed 5 nights in Sep 2025

10/10 Excellent

Cathy B.

Liked: Cleanliness
Stayed 2 nights in Sep 2024

8/10 Good

Brittany D.

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.
Stayed 4 nights in Aug 2025

8/10 Good

Ellen P.

The property is the perfect location. The check in and out were no problem. Could of been cleaner.
Stayed 7 nights in Aug 2025

10/10 Excellent

Paula C.

Liked: Cleanliness

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

10/10 Excellent

Jim F.

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

10/10 Excellent

Austin

Traveled with family and small children
Liked: Cleanliness, amenities, property conditions & facilities
Responsive owner, beautiful property.
Stayed 5 nights in Jul 2025

10/10 Excellent

Brad P.

Liked: Cleanliness
Stayed 4 nights in Sep 2024

10/10 Excellent

Lisa S.

Liked: Cleanliness

Family getaway

Beautiful home, great location for anywhere in Door County.
Stayed 5 nights in Aug 2024

6/10 Okay

Tonia F.

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

10/10 Excellent

Vanessa S.

Liked: Cleanliness

Family Vacation

Beautiful home. Great vacation and would definitely stay again.
Stayed 7 nights in Jul 2024

8/10 Good

Russ P., Indianapolis

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.
Stayed 5 nights in Jul 2024

10/10 Excellent

Kimberly O.

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!!
Stayed 4 nights in Jul 2024

10/10 Excellent

Candi S.

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.
Stayed 4 nights in May 2024

10/10 Excellent

Christiane M.

Liked: Cleanliness

Great family get together location

The property is beautiful, conveniently located and with amazing indoor and outdoor space
Stayed 2 nights in Oct 2023

10/10 Excellent

Jackie O.

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.
Stayed 3 nights in Sep 2023

10/10 Excellent

Nick V.

Liked: Cleanliness

Awesome lake house

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

10/10 Excellent

Maya A.

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.
Stayed 3 nights in Jul 2023