Cottage holiday rentals in Baileys Harbor

Dogs Stay Free! Waterfront Door County Cottage

Jiffy's Journey is a beautiful lake side cottage features stunning sunset views over Green Bay. Outside, enjoy easy, private water access, beautiful deck, and the stunning sunset views of Green Bay. Inside, enjoy the bright, updated open floorplan, with views of the bay from every room in the house, even the bathrooms! Upstairs the entire floor is a giant master suite that will wow you! During the day, you're just a short drive from all that Door County has to offer! Pet friendly and no pet fees

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!

The Charm of Door County

A delightful retreat in perfect DC location. Ideal for a romantic weekend for a couple or perhaps for a family with two younger children. The retreat has two very large rooms, one featuring a sumptuous King bed, glass-topped table and four upholstered chairs, the other has a library/living-room feel - with several hundred books decoratively arranged. This has a Queen Sofabed, largeTV with Cable Netflix & Prime, and mini-fridge, microwave, coffee-maker & basic dinnerware. Pretty, private patio.

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.

Pet-Friendly, Cozy Cottage in Northern Door County

- Pet-friendly, 2 bedroom home with A/C in Northern Door County - Indoor fireplace & outdoor bonfire pit (wood provided) - Screened porch to enjoy nature - 5 minutes from famous Curvy Road, Washington Island Ferry, Newport State Park & Europe Bay Beach - Short drive to neighboring villages - Sister Bay, Ellison Bay, Baileys Harbor, etc - Walk or bike (provided) to Hedgehog Harbor - Includes all amenities to make you feel at home - Need more space? Check out our neighboring cottages next door.

Logan Creek Cottage

We hope you love our newly renovated home on Logan Creek as much as we do! We took a lot of time to renovate the small cabin, wall to wall. The living room has abundant natural light with a picturesque window and large sliding glass doors over looking our porch and Logan Creek. All of these renovations were to increase the view of the natural beauty of the Logan Creek State Natural Area. We have two bedrooms + loft so it is perfect for your small family or just a cozy spot for two!

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 Stargazing Cottage modern home Door County

Modern and luxury cottage nestled in the woods. Perfect combination of being in nature yet enjoying the comfort of a well equipped home. Located in Carlsville, Town of Egg Harbor. Wineries and shops are less than a mile away. A quick drive will get you to downtown Egg Harbor and the beach. After a busy day exploring all that Door County has to offer, finish the night with a bonfire surrounded by stars and trees. This cottage was designed to make you feel right at home.

South Lane Cottage #1

This sweet 2 bedroom, 1 bath home, with a glimpse of Lake Michigan from the living room window. This location is in pristine condition, and has a newly remodeled kitchen. As well as a large Trex deck at the rear of the house. You can also take advantage of the short walk to Anclam park and waterfront fun, or the shops and restaurants in downtown Baileys Harbor. This is the second listing from the owners of Bearded Heart Coffee, which is located just down the road.

Waterfront Cottage · Kayaks · Firepit · Sun Porch

Sawyer Harbor Retreat is a private waterfront cottage tucked on the harbor, with a big open yard running down to the water and quiet that's hard to find. Kayak and chase sunsets in summer; come fall, it's golden mornings on the water, a round at Idlewild, and color hikes at Potawatomi State Park — all minutes from Sturgeon Bay. With 3 bedrooms, 2 full baths, and room for 10, it's an easy fit for families, couples, and friends after a relaxed Door County escape.

Sister Bay A-Frame, Fire Pit, Coffee Bar, Sleeps 4

Trade the hustle and bustle for peace and quiet at our cozy retreat, just 5 minutes from the heart of Sister Bay. Tucked away on 1.6 acres of serene woods filled with beautiful beech trees, the cottage is your perfect getaway spot. Kick back on the spacious front deck, unwind on the screened-in porch, and soak in the natural beauty all around. Inside, mid-century modern vibes meet cozy comforts, with everything you need for a relaxing, stress-free stay.

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.