Cottage holiday rentals in Sister Bay

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.

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.

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!

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.

The Sister Bay Getaway: Water View & Downtown!

Updated 2 bedroom home - smoke & pet free. WiFi, Smart TV and A/C. Walking distance to downtown Sister Bay shops, restaurants, beach and more! This has been a favorite Door County location for many! We sincerely hope you enjoy our vacation home, Sister Bay, and everything Door County has to offer! Accept rental agreement (House Rules) prior to your stay. Airbnb bills State/County Taxes (5.5%); Lodging (8%) & Resort (0.5%) taxes

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.

4 BR + Coffee Bar + Firepit + Disc Golf - Sleeps 8

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.