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Private wooded lot- Updated Baileys Harbor Home

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Smart TV, fireplace, DVD player, books - Private wooded lot- Updated Baileys Harbor Home (Baileys Harbor)
3 bedrooms, iron/ironing board, free WiFi, bed sheets - Private wooded lot- Updated Baileys Harbor Home (Baileys Harbor)
Terrace/patio - Private wooded lot- Updated Baileys Harbor Home (Baileys Harbor)
Smart TV, fireplace, DVD player, books - Private wooded lot- Updated Baileys Harbor Home (Baileys Harbor)
Full-sized fridge, microwave, oven, stovetop - Private wooded lot- Updated Baileys Harbor Home (Baileys Harbor)
Nestled on a 2.25 acre wooded lot, The Roost offers a serene retreat in Baileys Harbor. Enjoy the peace and serenity of the woods with the convenience of a short walk or drive to downtown Baileys Harbor and Lake Michigan, where you can visit shops, restaurants, and more! This home is equipped with Smart TV, Blu-Ray player and video library for entertainment.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6154 sq m

Popular amenities

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

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Private wooded lot- Updated Baileys Harbor Home

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

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

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
+ Washer, 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 flavors and a coffee bean grinder
+ Fully equipped kitchen (see amenities) includes ice maker, crockpot, and an additional full size fridge in the garage

Sleeping Accommodations:
Bedroom 1: King size bed, ceiling fan, room darkening shades, hangers, extra pillows and blankets.
Bedroom 2: Bunk bed set offers a twin size bed over a 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.

Our property is conveniently located the following distances from nearby favorites:
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 Harbor, 15 miles from Ellison Bay, 20 miles from Gills Rock

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:
This is a quiet community with residential neighbors. This home 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 #02-56-2886-07

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

Property amenities

Ski

  • Cross-country skiing nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car required
  • Onsite parking options include a garage

Food and drink

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Freezer
  • Full-sized refrigerator/freezer
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV
  • Video library

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Patio
  • Yard

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping

Location highlights

  • In a rural location
  • Near the bay
  • Near the marina

Things to do

  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Ice skating nearby
  • Sailing 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: 1,659 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 are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

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
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

We should mention

This property's policy is to refuse certain bookings for the purpose of group events or parties, including stag and hen parties
A car is recommended for transport to and from this property

Property is also known as

105

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. Take in the nearby slopes with cross-country skiing, or try out other outdoor activities such as ice skating. Visit our Baileys Harbor travel guide
View more Holiday homes in Baileys Harbor
Map
Baileys Harbor, WI

What's nearby

  • Great times and great beer.  Come around Mid June for the annual Door County Beer Fest.  Could that be Aaron Rodgers?  You never now who you'll run into up here. www.FunToBeFree.com
    Door County Brewing Company
    16 min walk - 1.4 km
  • Building at the Ridges Sanctuary nature preserve in Baileys Harbor, Wisconsin
    Ridges Sanctuary
    3 min drive - 2.2 km
  • What beautiful craftsmanship. #Lighthouses
    Cana Island Lighthouse
    14 min drive - 11.6 km
  • Anclam Beach Park
    20 min walk - 1.7 km
  • Baileys Harbor Ridges Park
    2 min drive - 1.8 km

Restaurants

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

Frequently asked questions

Is Private wooded lot- Updated Baileys Harbor Home pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Private wooded lot- Updated Baileys Harbor Home?

On-site parking is available at the property.

What time is check-in at Private wooded lot- Updated Baileys Harbor Home?

Check-in begins at 4:00 PM.

What time is check-out at Private wooded lot- Updated Baileys Harbor Home?

Checkout is at 10:00 AM.

Where is Private wooded lot- Updated Baileys Harbor Home 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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Private wooded lot- Updated Baileys Harbor Home 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. 18 out of 20 reviews
Rating 8 - Good. 2 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10

Cleanliness

9.8

Location

Reviews

10/10 Excellent

Mary D.

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

10/10 Excellent

Alex W.

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

Good stay

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

10/10 Excellent

gwen l.

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

10/10 Excellent

Michelle D.

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

10/10 Excellent

MaryJane Steinthal K.

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

10/10 Excellent

Kevin A.

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

8/10 Good

Lisa H.

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

10/10 Excellent

TIna S.

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

10/10 Excellent

Matthew K.

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

10/10 Excellent

Debra C.

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

10/10 Excellent

William v.

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

10/10 Excellent

Virginia M.

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

10/10 Excellent

Jodi J.

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

10/10 Excellent

Patricia P.

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

10/10 Excellent

Terri S., Eden Prairie, MN

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

10/10 Excellent

Jenna S.

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

10/10 Excellent

Melinda H.

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

8/10 Good

Charles X.

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

10/10 Excellent

Becky B.

Stayed 4 nights in Jun 2025