Cottage vacation rentals in Baileys Harbor

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.

Gull Cottage Waterfront Home on Washington Island

Find a little piece of heaven at Gull Cottage on Washington Island! Our charming cottage has been passed down through generations and is the perfect island get-away! Centered on Figenschau Bay, we are just minutes from restaurants, island landmarks and boat launches. This property has the comforts of home and the amenities of a boutique hotel! Newly renovated/interior painting/remodeled bath/new mattresses/bed linens/draperies. Fully equipped kitchen. Outdoor seating area w/deck and fire pit.

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.

Winding River Cottages-Pine Cone Cottage

The Pinecone Cottage is one of the units at Winding River Cottages on the Menominee. There is one other cottage and one house also on the property. This cottage is directly on the Menominee River, very close to Marinette, WI/ Menominee, MI. It has 2 bedrooms and 1 bath, a full kitchen with full-size stainless steel appliances (stove/oven, refrigerator, over-the-stove microwave), and a living area with a 50" TV, chair, and futon, which can convert into a full-size bed.

Cozy A-Frame - Coffee Bar, Fireplace - 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.

Sturgeon Bay Waterfront Cottage, Private beach.

Waterfront guest cottage on Door County's Gold Coast! Nestled among luxury homes, this quaint 1930's cottage has undergone an interior renovation while preserving its character on the outside. Two bedroom, one full bath, stocked kitchen, living room. Located steps from the bay with a private beach. Hear the gentle sound of waves lapping on the shore as you sleep. Bring your kayak and fishing poles. Perfect for anyone seeking a quiet retreat!

20% Off! 4 BR + Coffee Bar + Firepit + Disc Golf

May & June Sale! Book now and save 20% on remaining May & June dates—perfect for families, couples, or a quiet Door County escape! Pull off the highway to the charm of a century-old, lovingly restored cottage just minutes from downtown in the heart of Door County. Stonewall Cottage blends historic character with modern comfort, offering a peaceful escape for families, couples, or friends.

Countryside Cottage/Duplex Unit 7

Cottage is located 2 miles outside of Fish Creek on County F. Cottage has nostalgic charm with reasonable rates. Unit is part of a duplex. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.