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Private, Updated Baileys Harbor Home: The Roost

Photo gallery for Private, Updated Baileys Harbor Home: The Roost

A living room with a fireplace, a television, and a dining area. - Private, Updated Baileys Harbor Home: The Roost (Baileys Harbor)
A bedroom with a bed, a ceiling fan, a bedside table, a nightstand, and a window with blinds. - Private, Updated Baileys Harbor Home: The Roost (Baileys Harbor)
A modern kitchen with a dining area, wooden cabinets, and a chandelier. - Private, Updated Baileys Harbor Home: The Roost (Baileys Harbor)
A modern kitchen with a central island, bar stools, and a dining area with a chandelier. - Private, Updated Baileys Harbor Home: The Roost (Baileys Harbor)
A wooden coffee table with a clock, coffee maker, and bottles. - Private, Updated Baileys Harbor Home: The Roost (Baileys Harbor)
You can look forward to a firepit, a garden and laundry facilities at Private, Updated Baileys Harbor Home: The Roost. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Private, Updated Baileys Harbor Home: The Roost

  • Summary:

    Welcome to The Roost, hosted by Simple Life Rentals! Updated in 2023, this 3 bedroom, 2 bathroom, 1-story home showcases beauty in all the details. The home is situated on a private road, nestled on a 2.25 acre wooded lot with a large pull through driveway perfect if you are towing a boat.



    The Space:

    Enjoy the peace and serenity of the woods with the convenience of a short walk or drive to city centre Baileys Harbour and Lake Michigan. Visit shops, restaurants, the harbour, The Ridges Sanctuary, and more!



    Property Features:

    + Back patio with picnic table

    + Firepit with 6 chairs (please bring local firewood)

    + Yard games provided: tether ball, ladder golf, giant Jenga

    + Dog friendly - up to 2 dogs allowed

    + Internet Wi-Fi: Starlink great for working remote (due to the rural nature of the property, cell phone coverage can vary)

    + Smart TV

    + Blu-Ray player and video library

    + Sound system

    + Central air and heat

    + Wood burning fireplace (bring local firewood)

    + Dining table with seating for 6. Snack bar offers seating for 4

    + Washing machine, dryer, iron, ironing board and drying rack

    + Board games, puzzles, books and toys provided for guest's entertainment

    + Wine refrigerator

    + Bench and mudroom like area in garage for shoes/ etc

    + Coffee bar includes a traditional drip coffee maker, a Keurig, a French Press, frother, coffee syrup flavours and a coffee bean grinder

    + Fully equipped kitchen (see amenities) includes ice maker, crockpot, and an additional full size fridge in the garage



    Door County Tourism Zone Commission Permit #02-56-2886-07



    Sleeping Accommodation:

    - Bedroom 1: King size bed, ceiling fan, room darkening shades, hangers, extra pillows and blankets.

    - Bedroom 2: Queen size bed, room darkening shades, ceiling fan, hangers, extra pillows and blankets.

    - Bedroom 3: Queen size bed, ceiling fan, room darkening shades, hangers, extra pillows and blankets.

    - Additional sleeping space: Pull-out sofa couch in living room (full size bed)



    Bathrooms:

    - Bathroom 1: Full bathroom w/ a soaking tub, walk-in shower, double vanity, and hair dryer.

    - Bathroom 2: Full bathroom w/ tub and shower combo and hair dryer.



    Home Truths:

    -This is a quiet community with residential neighbors. This home is geared towards quiet family holidays. Due to the proximity of neighbors, we cannot accommodate bachelor or hen nights, reunions, or other rowdy gatherings.

    -This property allows up to 2 well-behaved dogs. There is an additional fee collected at booking.



    Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalise your reservation.



    Getting Around:

    - Our property is conveniently located the following distances from nearby favourites:

    - 3 miles from Kangaroo Lake and the Causeway

    - 12 miles from Cave Point County Park and White Dunes State Park

    - 8 miles from Fish Creek, 8.5 miles from Ephraim, 9.6 miles from Sister Bay, 10 miles from Egg Harbour, 15 miles from Ellison Bay, 20 miles from Gills Rock



    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 rubbish 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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About the area

Located in Baileys Harbor, this holiday home is in a rural area. The area's natural beauty can be seen at Lake Michigan and Peninsula State Park, while Door Shakespeare and Birch Creek Music Performance Center are cultural highlights. Peg Egan Performing Arts Center and Pirate's Cove Adventure Golf are also worth visiting. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Baileys Harbor travel guide
View more Holiday homes in Baileys Harbor
Map
Baileys Harbor, WI

What's nearby

  • A group of people sitting around a wooden table in a room with a window and a hanging light fixture.
    Door County Brewing Company
    16 min walk - 0.9 miles
  • An aerial view of a large lake with a small island and a residential area along the shore.
    Kangaroo Lake
    6 min drive - 1.8 miles
  • A forested landscape with autumn foliage and a distant island in the water.
    Peninsula State Park
    15 min drive - 9.7 miles
  • A lighthouse with a white tower and a dark top, surrounded by trees.
    Cana Island Lighthouse
    15 min drive - 8.3 miles
  • A silhouette of a person sitting on a rock by the sea during sunset.
    Egg Harbor Beach
    19 min drive - 12.8 miles

Restaurants

  • AC Tap
    8 min drive
  • Sway Brewing + Blending
    10 min walk
  • Coyote Roadhouse
    7 min drive
  • Roost + Banter
    16 min walk
  • Koepsel's Farm Market
    9 min drive

Frequently asked questions

Is Private, Updated Baileys Harbor Home: The Roost pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Private, Updated Baileys Harbor Home: The Roost?

On-site parking is available at the property.

What time is check-in at Private, Updated Baileys Harbor Home: The Roost?

Check-in begins at 4:00 PM.

What time is check-out at Private, Updated Baileys Harbor Home: The Roost?

Checkout is at 10:00 AM.

Where is Private, Updated Baileys Harbor Home: The Roost located?

Situated in a rural location, this holiday home is within a 15-minute walk of Door County Brewing Company and Lake Michigan. Baileys Harbor Ridges Park and Anclam Beach Park are also within 2 miles (3 km).

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Reviews

Private, Updated Baileys Harbor Home: The Roost Reviews

9.8

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 24 out of 27 reviews
Rating 8 - Good. 2 out of 27 reviews
Rating 6 - Okay. 1 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

Reviews

Verified review

10/10 Excellent

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

Good stay

Fun time! Good property and location!
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

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

Perfect Family Getaway

We really enjoyed our stay at The Roost. It was clean, cozy, comfortable and well appointed for our family. The location was also nice for the activities we had planned. Plus, it is pet friendly. I would stay at the Roost again and would higly recoomend.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

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

Beautiful home in a peaceful location

We loved our stay here! It was a quick drive to the places we wanted to visit, the neighborhood was very quiet, the home was beautifully uodated and all the amenities were thought of so we could relax and enjoy. The fire pit was a great place to visit and watching all the deer in the woods really made us feel like we were away from the hustle and bustle of town. We would love to stay here again next time we are in Door County.
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

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

Door County getaway

The home was beautiful. I was impressed with how well furnished it was. Anything you wanted/needed was available. Very well decorated and comfortable. Quiet setting.
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

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

Great stay

We are a family with adult children and their spouses. We loved staying at the Roost. It felt more like home than a rental. It had all the amenities we could have wanted. Beds were comfortable, it was clean, and it a good location. We will be back!
Stayed 5 nights in Jul 2023
Verified review

10/10 Excellent

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

Great stay!

We had a great stay in Bailey’s Harbor. This property is very comfortable and very clean. Beautiful and private setting in a very wooded area but close to town and the lake. The house is completely updated with so many nice extras like a coffee bar, fireplace and cozy fire pit with plenty of chairs The decor is beautiful… comfortable beds and very nice linens and towels. I wish our stay was longer so we could have enjoyed the fireplace inside! No issues except we had trouble opening the lock box at first but then got the hang of it.
Stayed 2 nights in Sep 2023
Verified review

8/10 Good

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

Fantastic decor!

We weren’t sure if our boat was going to make it up the long wooded road and there was a car in the driveway when we got there so we were a little worried. It was the cleaning crew who had us come back half an hour later. When we got in there we were absolutely blown away!! The decor was top notch and the layout was awesome! All 3 of us loved this cozy home in the woods so much that we didn’t want to leave. This was our first air b&b stay and it was absolutely perfect!! There was so much thought put into everything in this home. We are so glad we chose this place for our anniversary getaway.
Stayed 3 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect property to stay with our dog and our friends!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We appreciated being able to bring our dog, that was key to us.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

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

Clean and convenient

Nice place close to any where you may want to visit in Door County
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Birthday stay in Door County. Lovely house decorated for holidays and VERY comfortable beds. Plenty of space for all and our pup to enjoy. Quite wooded area, very cool to see wild turkeys roost every night. Guessing that's why the house is called the Roost. Very easy in and out and to have a garage space to load and unload Fantastic!! Will reserve again soon :)
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Can't say enough good things about our experience at this home. The communication with the managing company was the most efficient and friendly I've ever had. The house was very clean and so comfortable with many amenities. We loved the wooded area and the fire pit was a bonus. We will definitely book again!
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was not much to look at from the outside but the inside was beautiful. It was clean, modern and was stocked with anything you could want. Setting was very private and quiet, yet close to restaurants, and parks.
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was very clean. In a wooded area that was nice & quiet. We were able to bring our dog which was a bonus. Plenty of places to walk her right out the door of the home. Arguably the most comfortable bed I've ever had at a rental property whether it be at a hotel or a home/cabin rental.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

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

Very nice

Very nice place to stay and a quiet neighborhood
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

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

Wow! Location and amenities!

Convenient to everything in Door County, yet in a quiet woodsy setting. The home was fully equipped with what we needed for a long weekend with our adult children, their spouses and their sweet doggos. Relaxing and fun! Would rent this again in a heartbeat.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

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

Nicely Furnished Comfortable House

The house was very clean and nicely furnished. The owners put some thought into the decor. This house is within walking distance to Bailey’s Harbor, and in a quiet location. It’s also close to Maxwelton Braes and the Orchards Golf courses. Very easy to get to Egg Harbor and Sister Bay from this location.
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

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

Cute with all the amenities

This house was so cute! It had a full modern bar cart, coffee and tea bar, s’mores tray with skewers, and a well-stocked kitchen. The fire pit was well-stocked with wood. The location was just far enough from the main drag that you couldn’t tell it was peak tourist season! We couldn’t find a big grocery store in Baileys Harbor, so did end up going to Sister Bay, which was only 10-15 minutes from the house. Overall we had a great time!
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a beautiful home; laid out well and very comfortable with a well equipped kitchen, which we only used for breakfast, but we appreciated it just the same. The only thing it didn’t have was a generator, which would have been nice when we lost power due to a very big storm; but we were grateful for a neighbor, Lurana, who came to check the house the next morning and supplied a couple of gallons of water so we could take care of essentials. We were also pleasantly surprised to receive a generous gift card to Chives from the owners to compensate for the inconvenience of the power outage. We were able to enjoy the use of that before we left DC and the restaurant was wonderful. Thank you for thinking of us in this way! We appreciated it very much.
Stayed 4 nights in Aug 2025
Verified review

6/10 Okay

Liked: Cleanliness, check-in, location
Disliked: Listing accuracy
Location is quiet and convenient to Door County sites. The problem is the bunk bed over the bed in the yellow & blue room (the listing may now be updated) was not there upon check-in. We had 5 adults and 1 kid and booked this house specifically for the 3-bedroom set-up. I called the host and was told by the answering service someone would return my call, but they never did. I messaged the host and got a reply that we could buy an air mattress and we’d get reimbursed, but where would we find that? I decided to sleep on the pullout couch. When it was time for bed, I discovered the couch and pullout bed were covered in crumbs so clearly the house was not well-cleaned. Other cleaning issues were hairs in the bathtub of the primary bathroom and some dirty glasses. The host was fairly responsive via messaging, but automated messages also came that read as if everything is great so clearly they do not manage communication well when there is a problem. I had to ask for compensation for the bed issue, and I doubt it would have been offered otherwise. The kitchen is great. The living room could use another chair or two to accommodate 6 people. Be warned that the bathtub in the guest bathroom is slippery and there is no mat provided. I used to work in hospitality and now teach about it, so I tend to be more critical. However, I have never had a major issue like bedding being misrepresented when using P2P accommodations.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very close to everything and a great clean property in the woods that our kids and dog loved.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Stayed 4 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Stayed 4 nights in Jun 2025