Cottage vacation rentals in Baileys Harbor

Cole's Country Cottage •In The Heart of Fish Creek

Come relax at our very comfortable, homey, quiet space located in the heart of Fish Creek, just minutes from downtown, the beach, Peninsula State Park + popular restaurants and shops. We prioritize the cleanliness of our space + the comfort of our guests. Two bedrooms, a living room, kitchen + bathroom make it perfect for families - you get plenty of backyard space too! We provide coffee + a fully equipped kitchen and bathroom. Stay with us for some relaxation + see all Door County has to offer!

Sea Glass Cottage

Welcome to Sea Glass Cottage. Your Door County home away from home. This light and airy cottage is on the water with rock beach, beautiful sunrises, great room with beam ceilings & wood burning fireplace, kitchen ready for cooking and baking. A view of Lake Michigan from nearly every room. Perfect location for families or couples vacation. This cottage is tucked away on a wooded lot with an open backyard to enjoy sunshine and shoreline, or take a quick 5 minute drive to downtown Sister Bay.

Tiny Yellow Cottage in Gills Rock

Live small, unplug, and unwind at our cozy, clean, and charming cottage in peaceful Gills Rock. Away from crowds, this tiny retreat includes a living area with kitchenette, two full-sized beds with crisp cotton linens, plus a private patio, grill, fire pit—stunning sunsets just across the street. It’s the perfect home to recharge after a day exploring Door County. Just 15 minutes from the bustle of the bigger towns—close enough for adventure, far enough for peace. Located on scenic Highway 42.

Stone’s Throw Cottage

Unwind at this waterfront cottage! New Sleep Number bed! Located on Sand Bay Point, this cottage offers you beautiful views, a boaters dream and an opportunity to relax. Enjoy the Door County views as you watch the sunrise, head out for early morning fishing, or just relax and drink your coffee by the water. Tie up your boat to the single step dock or walk right into the private water access. This two bedroom one bath cozy cottage is a dream weekend getaway. Kayaks and life-jackets included.

Peace of Beach, 4 season waterfront cottage

Beautiful 4 season, private 2 bedroom Knotty Pine Cottage located on the shores of Lake Michigan just 10 yards away from water in Sturgeon Bay, WI. 2 BR/1 bath cottage with beautiful stone, wood burning fireplace. A fully equipped kitchen with high bar dining which seats 8. Lots of living space with leather sectional and full size hide-away sofa sleeps 2, Main Guest Room 1 w/ queen log bed and Guest Room 2 with full size log bunk beds, Large screen tv, wifi and panoramic lake view.

The Key to Happiness

Sleeping 4-6 between 4 beds, Plum Retreat provides a one-of-a-kind Door County experience. With 2 large bedrooms (plus giant living room with queen sofa bed, dining area and full kitchen), the 1700 sq-feet have a charming cottage-like feel. Conveniently located with gorgeous perennial gardens, it makes a romantic, peaceful or fun space. Private lawn & patio/grill. Pretty much everything has been thought of. Last summer, all 37 groups of people gave it a 5-star rating!

Lofted Pines Cottage

Settle in at Lofted Pines Cottage for your Door County stay! Located off the beaten path, but only a few minutes from downtown Sister Bay or Lake Michigan, Lofted Pines is elegantly situated among mature cedar and fir trees, yet open and airy. Whether you're relaxing on the wrap around porch, cozied up in front of the fireplace or enjoying the wood burning fire pit, Lofted Pines is the perfect spot to unwind after exploring the Door County Peninsula.

Glidden Cottage -Beach Access!

Our cottage is situated on the “quiet side” of Door County on the meandering Glidden drive along the Lake Michigan shoreline. The cottage is perched upon a small hill and surrounded by pine trees in a relaxed country setting. Guests have dedicated access to Lake Michigan right across the street. The sand beach provides for an excellent location for kayaking, sunbathing, swimming, and walks. Glidden Cottage is only five miles from Sturgeon Bay.

Door County Cottage, near Haines Beach!

This 3 bedroom, 2 bath Door County Cottage is walking distance to the beach and located on Sand Bay Point! This cottage has a peaceful setting that is tucked back into the woods and within walking distance of Haines Beach! We also have our "Family Fun Shed" full of kayaks, bikes, strollers and outdoor games for your use, at no charge! We are also child and dog friendly as well.