Cottage holiday rentals in Sister Bay

The exterior of a charming two-story cottage features a light-colored stone façade and a steeply pitched roof. Large front windows allow for natural light, while a welcoming front door is framed by two lanterns. Neatly landscaped shrubs line the walkway leading up to the entrance.

4.98 out of 5 average rating, 125 reviews

Cottage in the Creek- Centrally Located DoCo Oasis

This house is a passion project of four siblings. We grew up in this house and share a love for Fish Creek. Being at the center of the BEST town on the peninsula was amazing and we can't wait to share that experience with our guests. We have fully renovated our family’s cottage to make it perfect for a group of friends or family. We look forward to being the home base for your ideal Door County vacation! Come experience a place where all the fun is only a short stroll from your front door.

4.91 out of 5 average rating, 296 reviews

A lakeside view is captured, featuring a wooden swing under a shaded structure. Tall trees frame the scene on either side, with the water reflecting a clear blue sky. A gentle breeze seems to rustle the leaves, enhancing the peaceful ambiance.

Cottage in Washington

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.

4.92 out of 5 average rating, 106 reviews

The living area features warm wooden beams and a stone fireplace, creating a cozy atmosphere. Large windows provide natural light and a view of the outdoors. Comfortable seating is arranged with a sectional couch, two chairs, and a coffee table, inviting relaxation.

Cottage in Ellison Bay

Pet-Friendly, Cozy Cottage in Northern Door County

- Pet-friendly, 2 bedroom home in Northern Door County - Indoor fireplace and outdoor bonfire pit (wood provided) - Beautiful 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 - Perfect for a family getaway or a trip with friends - Includes all amenities to make you feel at home

A cozy cottage is framed by surrounding trees, featuring a stone fire pit in front. Large glass doors illuminate the interior from within, while wooden siding adds a natural touch. Two outdoor chairs are positioned nearby, offering a serene view of the landscape.

4.92 out of 5 average rating, 208 reviews

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.

A charming blue cottage with yellow shutters adorns the exterior. A well-maintained stone wall and vibrant flower beds enhance the entrance. The home features a single-car garage, a front porch, and large windows that invite natural light into the living space.

4.93 out of 5 average rating, 194 reviews

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 and remits the WI State/County Taxes (5.5%); Door County Lodging tax (8%) & Sister Bay Resort tax (0.5%).

A spacious living area features a dining table with six upholstered chairs surrounded by warm, red walls. A cozy seating arrangement includes a pink armchair and a black rocking chair near a fireplace, with large windows allowing natural light to fill the space.

4.96 out of 5 average rating, 121 reviews

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!

4.95 out of 5 average rating, 177 reviews

Cottage in Marinette

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.

The cottage showcases a distinctive A-frame design surrounded by lush greenery. A spacious wooden deck with yellow Adirondack chairs invites relaxation, while large front-facing windows allow for natural light and views of the serene wooded lot.

5 out of 5 average rating, 206 reviews

A-Frame - Coffee Bar, Gas 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.

A cozy cottage is nestled among tall trees, showcasing a white exterior with a stone chimney. The spacious porch features blue chairs, inviting relaxation. Lush green grass surrounds the home, complementing the peaceful rural setting.

4.99 out of 5 average rating, 152 reviews

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.

4.85 out of 5 average rating, 260 reviews

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.

An open living space features a large sectional sofa complemented by decorative pillows. A flat-screen television is mounted on the wall opposite, while a sleek coffee table occupies the center. The room is brightened by natural light from windows, revealing a modern kitchen in the background.

4.9 out of 5 average rating, 124 reviews

Door County Cottage, near Haines Beach!

Charming 3BR/2BA Door County cottage on Sand Bay Point! Peaceful wooded setting just a short walk to Haines Beach. Enjoy family fun with free access to our ‘Fun Shed’ stocked with kayaks, bikes, strollers & outdoor games. Perfect for relaxing, exploring, and making memories—child & dog friendly too!

The exterior of the cottage features a white facade with a brown roof. Two green chairs are positioned on the patio, surrounded by landscaped garden areas. Sunlight filters through the surrounding trees, creating a bright and inviting atmosphere.

4.76 out of 5 average rating, 196 reviews

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.

Popular amenities for Sister Bay cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The image captures a serene waterfront scene with colorful multi-story cottages reflecting on the calm water surface. The sky displays soft hues of blue and orange, indicating either early morning or late afternoon. Stone pathways and manicured landscapes are visible in the foreground.

4.87 out of 5 average rating, 91 reviews

Marina View Cottage 121

The exterior of the cottage is shown, featuring a pristine white facade and a prominent stone chimney. Lush greenery includes flowering pink bushes and manicured hedges, enhancing the inviting atmosphere. A spacious deck is visible at the rear, providing outdoor relaxation options.

4.79 out of 5 average rating, 47 reviews

Peninsula Parkview Sunset Meadow Whirlpool Cottage

An outdoor deck features a glass-top dining table surrounded by six chairs, set against a backdrop of lush greenery. Large windows with white shutters provide views of the water, while a door leads into the cottage.

4.7 out of 5 average rating, 64 reviews

Waterfront Cottage with 2 Bedrooms & Whirlpool!

Three distinct buildings are arranged around a landscaped area featuring green grass and meticulously maintained flower beds. A bicycle is parked along the winding pathway, which is surrounded by young trees and stone features, contributing to a sense of openness and inviting atmosphere.

4.87 out of 5 average rating, 95 reviews

Door County Waterfront Cottage (119)

4.91 out of 5 average rating, 11 reviews

Aspen Cottage at Cliff Dwellers Resort

The entrance to the cottage features a double door design with large glass panels. The number '1A' is displayed beside the door. Reflections of the outdoor area and waterfront can be seen in the windows, enhancing the inviting atmosphere.

4.69 out of 5 average rating, 32 reviews

Waterfront Studio Cottage with Whirlpool

Pet-friendly cottage rentals

4.86 out of 5 average rating, 94 reviews

A welcoming cottage entrance features a small wooden deck with two white adirondack chairs. Lush greenery and colorful flowers surround the space, while a light blue exterior contrasts against the natural setting. A screen door adds charm and accessibility.

Cottage in Egg Harbor

Village Cottage - walkable to waterfront and town

A broad deck overlooks the serene waters of Green Bay, featuring a striped awning providing shade. The calm surface of the water reflects the sky, while rocky beach areas are visible below. Surrounding trees frame the tranquil view, enhancing the natural setting.

4.77 out of 5 average rating, 74 reviews

Sister Bay Rental- Water Front Cottage

The exterior of the cottage showcases a spacious wrap-around porch, elevated on a stone foundation. The home is surrounded by a grassy area, with trees providing a natural backdrop. Large windows invite plenty of natural light into the interior spaces.

4.77 out of 5 average rating, 120 reviews

The Bungalow at Potawatomi State Park

Cottage in Washington Island

The serene water reflects the vibrant colors of a sunset, showcasing soft oranges and yellows blended with hints of blue. Gentle ripples create texture on the surface, enhancing the tranquil atmosphere of the waterfront setting.

4.83 out of 5 average rating, 103 reviews

Charming Waterfront Cottage

4.93 out of 5 average rating, 103 reviews

An aerial view of a quaint blue cottage surrounded by lush greenery and tall trees. A spacious lawn extends around the cottage, with a few seating options visible. In the background, a serene waterway is nestled among the trees, enhancing the peaceful atmosphere.

Cottage in Stephenson

Charming Cabin Perfect for Relaxing!

A comfortable living area features a light-colored sofa adorned with cushions. A wooden coffee table sits in front of it, accompanied by a plush ottoman. Natural light enters through large windows, highlighting a decorative electric fireplace and a television mounted above the mantel.

4.96 out of 5 average rating, 121 reviews

CREEKSIDE COTTAGE Downtown yet off the beaten path

The exterior of the cottage is shown, featuring a light-colored siding and a welcoming front door. A small porch area is visible, surrounded by greenery. The window beside the entrance allows natural light into the interior, contributing to the peaceful ambiance of the property.

4.73 out of 5 average rating, 15 reviews

Door County Bungalow

4.89 out of 5 average rating, 28 reviews

A charming green cottage features a welcoming entrance with a white railing and wooden steps leading up to the front door. A grassy area surrounds the structure, and the view beyond the porch showcases serene lake scenery.

Cottage in Ellison Bay

Lake View at Europe Lake Lodge

Private cottage rentals

5 out of 5 average rating, 12 reviews

Cottage in Marinette

Riverside Cottage on ATV Trails with Kayaks

A gravel area features a stone fire pit surrounded by six Adirondack chairs, facing the serene waters of North Bay. Lush greenery and a clear blue sky enhance the tranquil atmosphere of this outdoor space.

Cottage in Baileys Harbor

4.77 out of 5 average rating, 13 reviews

Baileys Harbor Waterfront Vacation Rental w/ Grill

The exterior of Kookaburra Cottage is showcased, featuring a charming white facade with a blue front door. Two rocking chairs and a small table are positioned on the porch, surrounded by lush greenery, creating a serene atmosphere in the wooded setting.

Cottage in Baileys Harbor

4.76 out of 5 average rating, 50 reviews

Kookaburra Cottage at Kangaroo Lake

A cozy cottage is positioned near the water's edge, surrounded by green grass. A wooden deck features outdoor seating and a BBQ grill. The American flag stands tall beside the cottage, while tranquil bay views are framed by subtle evening light.

Cottage in Oconto

4.67 out of 5 average rating, 100 reviews

Waterfront on Green Bay Cottage! UpNorth *Fishing*

The charming cottage features a blue exterior and a welcoming porch with railings, surrounded by lush greenery. A stone pathway leads to the entrance, while a swing set can be seen nearby, nestled among the trees.

Cottage in Baileys Harbor

4.89 out of 5 average rating, 18 reviews

StayLakeside in NorDor @ The Harbor House

4.95 out of 5 average rating, 61 reviews

A charming cottage exterior is framed by surrounding woods, featuring a covered front porch with white railing and steps leading to the entrance. Multiple windows allow for natural light, while a gravel path leads to the parking area and yard.

Cottage in Ephraim

Maple Grove Cottage is your next relaxing get away

An outdoor deck is surrounded by lush green trees, providing a tranquil setting. The area features a round table with four chairs and a built-in bench. Light filters through the leaves, creating a peaceful atmosphere for meals or relaxation.

4.84 out of 5 average rating, 112 reviews

Updated Home w/ Deck: 2 Mi to Sister Bay Beach!

The exterior of a green cottage is featured, showcasing large windows and a wooden deck. A dining table with white chairs is positioned on the deck, surrounded by a grassy area. A stone pathway leads toward the entrance, with trees visible in the background.