Skip to content
Simple Life Rentals

Choose your stay

Book directly with Simple Life Rentals.

Winding Lane Hideaway Dog Friendly Door County

3 bedrooms · 5 beds · 1 bathroom · Sleeps 6
CottagePet friendly

Where you’ll sleep

Queen
Bedroom 1
2x Twin
Bedroom 2
2x Twin
Bedroom 3

Peaceful, pet-friendly cottage steps from Lake Michigan's North Bay.

  • –Pet-friendly seclusion just steps from Lake Michigan's North Bay.
  • –Tranquil cottage backed by nature conservancy, offering peace and quiet.
  • –Family-focused amenities including bikes, games, and easy water access.

Welcome to Winding Lane Hideaway, hosted by Simple Life Rentals! This comfortable, pet-friendly cottage offers peace and quiet away from the crowds, secluded against nature conservancy-protected land just feet from the boat ramp into Lake Michigan's North Bay. Enjoy a spacious kitchen, breakfast ...

About this property

Welcome to Winding Lane Hideaway, hosted by Simple Life Rentals! This comfortable, pet-friendly cottage offers peace and quiet away from the crowds, secluded against nature conservancy-protected land just feet from the boat ramp into Lake Michigan's North Bay. Enjoy a spacious kitchen, breakfast bar, and inviting patio, all just a short drive from Door County's harbor towns.

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

Property Features:
+ Dog Friendly!
+ Secluded location backed by nature conservancy land
+ Smart TV with streaming (Prime Video, Peacock, Paramount)
+ DVD player (please bring your own DVDs)
+ Board games, puzzles, and books
+ Starlink Wi-Fi
+ Washer and dryer on site
+ Fully equipped kitchen with breakfast bar (see amenities)
+ 2 adult bikes and a set of golf clubs available for guest use
+ Paved driveway with room for boat and trailer
+ Forced air heat
+ Central A/C (new in 2026!!)

Sleeping Configuration:
Bedroom 1 (main level): Queen size bed
Bedroom 2 (main level): Two twin beds
Bedroom 3 (main level): Two twin beds

Bathrooms:
Bathroom 1 (main level): Full bathroom with walk-in shower

Outdoor Area:
Patio with table and 6 chairs
Fire pit with 6 chairs (please bring your own firewood)
Hammock
Propane grill
Outdoor games: basketball (mobile hoop), bocce ball
3 parking spots available in driveway
Room for boat and trailer

Water Access:
Located on North Bay (Lake Michigan) - not directly waterfront, just steps from the Winding Lane boat ramp
Water is swimmable; very calm, especially on the north/west side of the bay
Shoreline is marshy to the north/northwest and rocky to the south/east
Water shoes recommended
Boat ramp at the end of the lane suitable for jet skis and smaller watercraft (depending on water level); approximately 1–3 feet deep at the ramp

Home Truths:
No dock at this property; watercraft docking is not allowed
Cell reception is moderate due to the rural nature of the property

Door County Tourism Zone Commission Permit #32-56-3029-07

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

The area

This home is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors and municipal restrictions, we cannot accommodate parties at the property including bachelor or bachelorette parties, reunions, weddings, or other gatherings.

Notes from your host

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).

full description, the area, host notes


Managed by Simple Life Rentals


Spaces


Guest Reviews

4.6★ · 15 reviews
All reviews →
★★★★★

“We had a wonderful weekend away. With two dogs it’s hard to vacation and bring them along but this place was perfect for my husband and I with our two dogs. Private back yard and overall quiet area. House itself was a nice size as well with everything we needed. Grill was nice as well. Host was responsive. Had one quick snafu where the code didn’t work for the door but they responded in minutes and resolved the really non-issue so quickly. We were very happy and would book again for sure.”

Cindy · Sep 2026

★★★★★

“Quiet neighborhood with a good location to enjoy all of the Door County attractions. The home was impeccably clean especially considering that it is dog friendly. We also appreciated the room configuration with two single beds in two rooms and queen bed in the other room. It was a great stay for our family visit.”

Guest · May 2026

★★★★★

“The property and host were everything we could have wanted or needed for our Door County stay. The communication with the property manager was prompt, clear, informative, and friendly throughout the entire rental process. The property was as pictured and described, if not better. We did have one issue arise during our stay, which was handled brilliantly. The air conditioning at the location stopped working on an extremely hot day. I reported that to the property manager and they worked with the owner to send someone out immediately. The issue was resolved entirely in less than two hours despite being after typical work hours. Something like that can ruin a vacation, but in our case it was just the most minor inconvenience that was fixed about as fast as humanly possible. I cannot say enough good things about how well that situation was handled. I highly recommend the rental and would return to the property in a heartbeat. The entire experience was how renting a house should be. Five stars all the way!”

Patrick · Jul 2026

Good for

PetsRemote work


Rules & Policies


Location

Baileys Harbor, Wisconsin

Get directions →

Choose your stay

Select dates to see availability

2 guests
Your stay