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, 143 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.

4.92 out of 5 average rating, 119 reviews

The viewing tower features large windows that provide a panoramic view of the bay and surrounding greenery. Soft lighting is created by decorative lanterns along the ceiling. A cozy ottoman sits on the wooden floor, complementing the warm wooden walls.

Cottage in Green Bay

Waterfront cottage with tower and hot tub!

This charming cottage is an ideal respite for your family holiday to the one-of-a-kind Green Bay, Wisconsin! Look forward to exploring this historic city, visiting iconic museums, and experiencing the vibrant Packers culture. The vacation rental home sits right on the water - offering fantastic views of the bay - and is just 10 miles from downtown. After the day's adventures, return to this cozy 3-bed, 1.5-bath house and unwind as your furry friends or children play in the waterfront yard!

4.92 out of 5 average rating, 103 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, 114 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, 207 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.

The image captures a serene sunset over a calm lagoon, reflecting vibrant orange and yellow hues on the water's surface. Lush trees frame the background, while a wooden dock lines the foreground, leading to a boathouse nestled along the shore.

4.95 out of 5 average rating, 184 reviews

Private Boat Launch! Door County Waterfront

Looking for a great get away? Love the water? Sunset Lagoon is perfect! Use the paddle boat or kayaks (included), bring your boat to get out and enjoy the water. Or relax and fish right off the deck! On site private boat launch and docking in a sheltered lagoon connected to Riley’s Bay. When you get back from the beach or fishing, light a fire, roast Smore's or sit on the deck and relax. Put some burgers on the grill and grab a cold one. Enjoy the good life at Sunset Lagoon!

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, 193 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, 120 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, 203 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, 148 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 framed by natural greenery, featuring large windows that allow for ample light. A gentle slope leads to a private sandy beach, where a kayak is visible on the shore. Relaxing lounge chairs are positioned in the yard, surrounded by grass and flowers.

4.96 out of 5 average rating, 376 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!

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, 122 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 cottage rentals in Baileys Harbor

Kitchen

Wifi

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.

Cottage in Fish Creek

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.

4.71 out of 5 average rating, 63 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)

4.89 out of 5 average rating, 9 reviews

Aspen Cottage at Cliff Dwellers Resort

4.96 out of 5 average rating, 76 reviews

A hot tub is positioned on a wooden deck, overlooking a tranquil bay. Soft lighting adorns the surrounding trees, enhancing the relaxing atmosphere. The water appears inviting with gentle ripples reflecting the soft colors of the sunset in the distance.

Cottage in Ellison Bay

Insta-worthy Waterfront Cottage with Hot Tub

The exterior of a charming cottage is depicted, showcasing a combination of stone and wood siding. Two comfortable chairs sit on a small porch area, with a garden featuring vibrant green plants and a stone wall enhancing the picturesque setting.

Pine 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.

4.68 out of 5 average rating, 31 reviews

Waterfront Studio Cottage with Whirlpool

Pet-friendly cottage rentals

4.86 out of 5 average rating, 93 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

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, 55 reviews

Cottage & Bay: Home with Game Room Near DT SB

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.

4.82 out of 5 average rating, 101 reviews

Charming Waterfront Cottage

4.85 out of 5 average rating, 78 reviews

An outdoor seating area features round dining table and six chairs, paired with two Adirondack chairs, surrounded by lush trees. The grassy yard leads to Lake Michigan, providing a serene lakeside backdrop.

Cottage in Algoma

Lakefront Cabin! Amazing Views, Fireplace, Cozy

4.91 out of 5 average rating, 295 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!

Private cottage rentals

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, 49 reviews

Kookaburra Cottage at Kangaroo Lake

4.91 out of 5 average rating, 47 reviews

The cottage exterior features a blue wooden facade with a metal roof, surrounded by lush greenery. A covered porch with wooden beams offers seating and overlooks a landscaped area with stones. The property is set in a tranquil, natural environment, providing a secluded atmosphere.

Cottage in Egg Harbor

Cozy cottage in Egg Harbor

4.95 out of 5 average rating, 60 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, 111 reviews

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

A fire pit is filled with burning logs, producing wisps of smoke that rise into the evening sky. In the background, a tranquil shoreline meets the water, reflecting shades of orange and pink from a sunset, creating a serene atmosphere.

4.88 out of 5 average rating, 76 reviews

The Riley’s Bay Beach Cottage

5 out of 5 average rating, 54 reviews

The white cottage is nestled among trees, with a well-maintained lawn leading to the entrance. An American flag is displayed prominently in front. The exterior features a combination of window styles, blending with the natural surroundings.

Cottage in Oconto

Bay Breeze Cottage - 4 Season Vacation Getaway!

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.

4.71 out of 5 average rating, 14 reviews

Door County Bungalow