Cottage holiday rentals in Sister Bay

The exterior of the cottage features a green facade with white accents, framed by vibrant flower planters. A decorative rooster sculpture stands beside the entrance, while gravel pathways and mulch beds enhance the natural surroundings. Windows are dressed with dark shutters, contributing to a welcoming ambiance.

4.93 out of 5 average rating, 189 reviews

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 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.

A serene lakeshore scene displays calm waters reflecting a clear blue sky. Gentle ripples move across the surface, while lush greenery frames the shoreline. A small boat is anchored nearby, offering a glimpse of leisure amidst the natural beauty. Rocky edges and smooth stones are present along the water's edge.

4.92 out of 5 average rating, 145 reviews

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.

4.93 out of 5 average rating, 117 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 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.

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.

4.94 out of 5 average rating, 202 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%).

4.9 out of 5 average rating, 109 reviews

A contemporary living area features a cozy electric fireplace mounted on a wooden accent wall, with a media console beneath it. In the background, an open kitchen and dining space are visible, highlighted by quartz countertops, dark bar stools, and a large dining table surrounded by chairs.

Cottage in Egg Harbor

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.

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, 132 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, 195 reviews

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.

5 out of 5 average rating, 235 reviews

Sister Bay A-Frame w/ Coffee Bar & Fire Pit

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, 169 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.

4.96 out of 5 average rating, 391 reviews

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!

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, 123 reviews

CREEKSIDE COTTAGE Downtown yet off the beaten path

Secluded & tranquil, yet still walkable to everything in Fish Creek. Have the best of both Door County worlds in this beautifully decorated, meticulously clean & maintained creekfront cottage. Enjoy downtown Fish Creek, with all the shops, restaurants, beaches & historic spots it has to offer. Directly across the creek from Peninsula State Park. Centrally located in the peninsula, you’re a short drive to anywhere you want to go. #1253189000

Popular amenities for cottage rentals in Sister Bay

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

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.

4.81 out of 5 average rating, 53 reviews

Peninsula Parkview Sunset Meadow Whirlpool Cottage

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.

4.7 out of 5 average rating, 37 reviews

Waterfront Studio Cottage with Whirlpool

Superhost

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

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.

4.72 out of 5 average rating, 82 reviews

Waterfront Cottage with 2 Bedrooms & Whirlpool!

New place to stay

Cabin w/ hot tub near Cana Island Lighthouse

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)

4.9 out of 5 average rating, 21 reviews

Aspen Cottage at Cliff Dwellers Resort

4.97 out of 5 average rating, 86 reviews

Cottage in Ellison Bay

Insta-worthy Waterfront Cottage with Hot Tub

Pet-friendly cottage rentals

Superhost

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, 121 reviews

The Bungalow at Potawatomi State Park

4.97 out of 5 average rating, 59 reviews

Private Nature Retreat With Game Room

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

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.

4.89 out of 5 average rating, 132 reviews

Door County Cottage, near Haines Beach!

4.79 out of 5 average rating, 73 reviews

A well-maintained cottage is surrounded by lush green grass and trees, featuring a welcoming front porch with seating. The exterior showcases light-colored siding with dark trim, complemented by vibrant landscaping, creating a cozy and inviting appearance.

Cottage in Ellison Bay

Sunny Cottage in Ellison Bay

4.91 out of 5 average rating, 299 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

4.93 out of 5 average rating, 105 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!

Superhost

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.

4.77 out of 5 average rating, 211 reviews

Countryside Cottage/Duplex Unit 7

Private cottage rentals

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.

4.79 out of 5 average rating, 14 reviews

Baileys Harbor Waterfront Vacation Rental w/ Grill

4.95 out of 5 average rating, 63 reviews

Bayside Bayframe on Sturgeon Bay Waterfront

A green lawn overlooks Rileys Bay, dotted with several trees. A cozy seating area with chairs faces the water, while a dock extends into the bay. Two kayaks are visible on the shoreline, surrounded by natural scenery.

5 out of 5 average rating, 32 reviews

Waterfront Home: Kayaks, Bikes & Custom Trip Plans

A charming cottage is set among tall trees, featuring a welcoming porch with steps leading to the entrance. An American flag gently flutters in the breeze. Lush green landscaping surrounds the property, enhancing the peaceful outdoor environment.

Cottage in Egg Harbor

4.85 out of 5 average rating, 13 reviews

Cute Door County Cottage minutes from Downtown!

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.

4.89 out of 5 average rating, 19 reviews

Restored 1920s Cottage | 4 Mins to Sister Bay

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.

4.83 out of 5 average rating, 63 reviews

Private Fish Creek Cottage in the Woods

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, 117 reviews

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

A wooden staircase leads down to a beach area framed by green trees. A hammock is visible in the background along the shore, with chairs placed on the sandy beach under a clear blue sky.