Cottage holiday rentals in Baileys Harbor

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, 144 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.

Two comfortable checkered armchairs are positioned around a small round table in front of a white-brick fireplace. Warm wood paneling covers the walls, complemented by light from windows on either side. A rustic mirror is mounted above the fireplace, enhancing the cozy ambiance.

4.96 out of 5 average rating, 324 reviews

Logan Creek Cottage

We hope you love our newly renovated home on Logan Creek as much as we do! We took a lot of time to renovate the small cabin, wall to wall. The living room has abundant natural light with a picturesque window and large sliding glass doors over looking our porch and Logan Creek. All of these renovations were to increase the view of the natural beauty of the Logan Creek State Natural Area. We have two bedrooms + loft so it is perfect for your small family or just a cozy spot for two!

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.

4.93 out of 5 average rating, 219 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.

4.9 out of 5 average rating, 108 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, 128 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!

A modern kitchen is equipped with stainless steel appliances and ample cabinet space. Natural light enhances the sleek countertops and warm wood flooring. Small decorative frames are positioned on the counter, adding a personal touch to the inviting space.

4.95 out of 5 average rating, 194 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.

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, 230 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, 162 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.

The exterior of the cottage is visible, elevated on a small hill surrounded by lush green ferns and trees. A wrap-around deck features railing, offering a view of the surrounding nature and enhancing the tranquil setting.

4.86 out of 5 average rating, 272 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.

4.98 out of 5 average rating, 132 reviews

Waterfront Sawyer Harbor Cottage

Welcome to Sawyer Harbor Retreat — a peaceful waterfront cottage on Sawyer Harbor. Enjoy kayaking, sunsets, and quiet lake mornings just minutes from Sturgeon Bay, Idlewild Golf Course, and Potawatomi State Park. With 3 bedrooms, 2 baths, and room for up to 10 guests, it’s ideal for families, couples, and friend groups seeking a relaxed Door County escape.

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, 130 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!

Popular amenities for Baileys Harbor cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.81 out of 5 average rating, 52 reviews

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.

Cottage in Fish Creek

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

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.

4.71 out of 5 average rating, 79 reviews

Waterfront Cottage with 2 Bedrooms & Whirlpool!

4.96 out of 5 average rating, 74 reviews

A welcoming sign for Dandelion Acres Vacation Rentals is displayed prominently, surrounded by colorful flowers in shades of pink and purple. Lush green trees frame the view, contributing to a serene outdoor setting.

Cottage in Crivitz

The Cottage at Dandelion Acres

4.92 out of 5 average rating, 139 reviews

A charming cottage features a unique tower with large windows, providing scenic views. Lush greenery surrounds the home, and a spacious yard invites outdoor activities. A cozy front porch is accessible, while a fire pit sits on the lawn, enhancing the outdoor experience.

Cottage in Green Bay

Waterfront Cottage with Tower and Hot Tub!

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)

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

4.93 out of 5 average rating, 30 reviews

Cottage in Ellison Bay

Wood View at Europe Lake Lodge

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

4.93 out of 5 average rating, 114 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

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

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!

4.77 out of 5 average rating, 209 reviews

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.

Cottage in Fish Creek

Countryside Cottage/Duplex Unit 7

4.96 out of 5 average rating, 180 reviews

Cottage in Marinette

Winding River Cottages-Pine Cone Cottage

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.

4.77 out of 5 average rating, 13 reviews

Baileys Harbor Waterfront Vacation Rental w/ Grill

4.6 out of 5 average rating, 236 reviews

The exterior of a barn red A-Frame structure is framed by lush greenery, revealing a sloped roof and comfortable deck space. An inviting entryway features wooden steps leading to the outdoor area, creating a welcoming atmosphere in a serene woodland setting.

Cottage in Egg Harbor

Quaint Cozy A-Frame in Door County

5 out of 5 average rating, 76 reviews

A stunning sunset over Green Bay displays a vibrant array of pink and purple hues in the sky. The shoreline is visible in the foreground, accompanied by silhouettes of trees and grasses that frame the peaceful waterfront scene.

Cottage in Green Bay

Private safe clean waterfront cottage on Green Bay

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.

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.

4.89 out of 5 average rating, 18 reviews

Restored 1920s Cottage | 4 Mins to Sister Bay

4.98 out of 5 average rating, 336 reviews

Cottage in Fish Creek

The Glass House on Birch Bluff

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.