Cottage holiday rentals in Sister Bay

4.93 out of 5 average rating, 120 reviews

A spacious deck extends towards the water, offering views of the calm lake. Lush green grass borders the shore, where rocky outcroppings meet the water. Surrounding trees provide a natural backdrop, creating a serene environment for relaxation.

Cottage in Brussels

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

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, 126 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.

4.74 out of 5 average rating, 100 reviews

Cozy Cabin! Amazing Location in Fish Creek! Pool!

Little Yellow Cottage is in the heart of Downtown Fish Creek. Featuring 2 cozy bedrooms, living room, full kitchen, 3 Roku-TV's, wifi, whirlpool tub/shower, & outdoor swimming pool. Enjoy the off-site "Adventure Shed" bikes and kayaks to use at Peninsula State Park or surrounding areas. We have a grill, coolers and games! Located just steps from Peninsula State Park, Sandy Fish Creek public beach, & the best local restaurants. Kid & dog friendly. *Please read description in full before booking*

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.

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

The Bungalow at Potawatomi State Park is a newly updated cottage only minutes from all that Door County has to offer! Located on a private 12 acre wooded lot with walking trails surrounded by vacant land you can enjoy the peace and quiet of Door County! Potawatomi State Park is only about a 5 minute walk away which offers boat launch, cross country skiing, swimming, kayaks, hiking, biking, snowmobiling and more! The Cottage is 2.5 miles to downtown Sturgeon bay as well! AC and Internet!

4.93 out of 5 average rating, 107 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 two-story cottage is situated near the water, showcasing a light yellow exterior and a dark roof. A second-story balcony is visible, along with a porch on the main level. Colorful chairs are arranged on the grassy area in front of the cottage, and a stone seawall borders the shoreline.

4.93 out of 5 average rating, 115 reviews

Yellow Marina Cottage

Welcome to our Door County Cottage in the heart of historic Sturgeon Bay! Our cozy marina cottage is the best of both worlds. It is located right on the water having its own private dock, yard, and fire pit. It's also close to downtown. Walk to restaurants, shops, parks, and marinas. Our cottage is an older home that has been extensively renovated with modern appliances. Enjoy watching the boat traffic from the second story deck. Two kayaks are provided or bring your own boat.

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, 195 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, 122 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!

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, 207 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, 153 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.

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)

4.92 out of 5 average rating, 12 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

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

An outdoor fire pit area is surrounded by Adirondack chairs, where guests gather around a crackling fire. The charming cottage is partially visible in the background, adorned with string lights and accessed by a wooden deck, providing a cozy setting for night-time gatherings.

4.96 out of 5 average rating, 57 reviews

Cottage & Bay: Home with Game Room Near DT SB

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, 125 reviews

Door County Cottage, near Haines Beach!

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

4.97 out of 5 average rating, 236 reviews

Cottage in Marinette

Winding River Cottages-Evergreen Cottage

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.

4.69 out of 5 average rating, 16 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

A modern cottage exterior is surrounded by lush greenery, with a large front window allowing natural light to illuminate the interior. The well-maintained lawn features patches of grass, and a paved driveway leads to the entryway, providing easy access.

4.75 out of 5 average rating, 28 reviews

The Cotter Cottage-Sister Bay

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

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

The exterior of a red cabin is visible, surrounded by dense greenery. A stone patio with a seating area is featured in the foreground. Large windows allow light to fill the interior, and a welcoming wreath hangs on the front door.

4.82 out of 5 average rating, 62 reviews

Private Fish Creek Cottage in the Woods

Cottage in Ellison Bay

4.53 out of 5 average rating, 45 reviews

Cozy remodeled 1-bed 1-bath, multi unit building

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.