Vacation rentals with outdoor seating in Baileys Harbor

The open-concept kitchen and dining area features green cabinetry and stainless steel appliances. A round braided rug is placed under the dining table, surrounded by modern chairs. Natural light fills the space, highlighting the adjacent living area with comfortable seating and decorative accents.

4.92 out of 5 average rating, 118 reviews

Cozy & Relaxing Wooded Home; Close to Everything!

Relax with the family at this quiet, spacious, and secluded 3 bedroom, 1.5 bath home. Just up the road from Lake Michigan and charming downtown Bailey's Harbor, our central location makes it a breeze to visit all of Door County - Sister Bay, Fish Creek, and Ephraim are all just minutes away. Hikers will enjoy the nearby Ridges Sanctuary, Toft Point, and more. This property allows for proximity to all of the fun, while allowing a tranquil and quiet place to stay and relax while on vacation.

4.96 out of 5 average rating, 241 reviews

The exterior of a cozy cottage is framed by lush green foliage. A white façade features a peaked roof and a small front porch with a large door. Sunlight filters through the leaves, creating a serene atmosphere in the surrounding garden.

Guesthouse in Fish Creek

Vintage Mod Cottage with fireplace & soaking tub!

Grandview Farm Cottage is a circa 1920s newly renovated, 420 sq. ft. private guesthouse on the grounds of a 2.5 acre Door County property built in the late 1800s. Modern, industrial and repurposed style meets vintage farmhouse charm. Central location allows for quick drive or even a bike ride to either coast of the peninsula. Enjoy nature, wildlife, your own organically grown gardens, and dark starry night skies, while being only 3 miles to nightlife and shopping and beaches and parks.

Farm stay in Baileys Harbor

A wide view of the farm landscape features golden grasses swaying in the breeze, with two large silos visible in the distance. Various farm buildings are spread out under a clear blue sky, framed by trees displaying autumn colors.

4.95 out of 5 average rating, 246 reviews

A True Farmhouse Experience

How would you like to get away from it all? How would you like to just kick back, relax, and take things in like the good ‘ol days? The Farmhouse might just be the place for you. Located just outside the town of Baileys Harbor, the Farmhouse is located on Gray-Aire Farms, a working farm since 1960. Nestled in the gorgeous surroundings of Northern Door County, you’ll be able to kick your feet up and take in the fresh country air, while watching the cows graze in the pasture.

A spacious wooden deck overlooks the tranquil waters of Lake Michigan, featuring a round table surrounded by black metal chairs. Long benches line the edges, offering additional seating. Lush greenery can be seen along the shoreline, enhancing the serene atmosphere.

4.91 out of 5 average rating, 337 reviews

Never Want to Leave Cottage

Three bedroom, lake home on the shores of Lake Michigan. Step into a beautiful, comfortable, clean environment on quiet North Bay in Door County, Wisconsin. As hosts, we have always taken great care to provide a safe and clean environment for our guests. To protect our guests, we are following the cleaning and sanitizing guidelines based on recommendations from the Centers for Disease Control and Prevention (CDC). We look forward to hosting you! Permit Number: 32-56-1996-00

Guest suite in Egg Harbor

A cozy studio space is accentuated by a wooden vaulted ceiling. A spacious bed is dressed in light, patterned bedding, while a comfortable couch is positioned beside a small table. Soft lighting from a lamp and an inviting rug contribute to the warm ambiance.

4.95 out of 5 average rating, 287 reviews

Cozy Farmhouse Studio

The 16 X 19 foot private studio, is located on the second story of our 120 year old farmhouse and has a private entrance and drive. It is equipped with its own kitchen, bathroom, balcony, queen bed, couch and closet. Our farmhouse is located on five scenic acres adjacent to our pottery studio and gallery. Please be aware that we have no air conditioning. It usually cools off at night, so it’s not typically necessary. We have a ceiling and cooling fan for the hot days.

A spacious living area is highlighted by a variety of seating options, including a beige sofa, a red armchair, and a classic wooden accent table. Natural light filters through windows, illuminating the colorful area rug and wooden floor, while decorative wall elements add charm to the space.

4.99 out of 5 average rating, 119 reviews

♦♦Relaxing, Historic and Hip Havngård House♦♦

Havngård House is a charming and historic home located in downtown Baileys Harbor, which has fast become the center of all the action in Door County! Walk to the marina, beaches, shops & restaurants. Hike & explore the unique ecology of the beautiful Ridges Sanctuary across the street. Catch live music & great beer at the Door County Brewing Company! The ultimate base for festivals like the Door County Beer Festival, Peninsula Century Ride, Fourth of July and Autumn Fest!

4.99 out of 5 average rating, 196 reviews

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.

Cottage in Sister Bay

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.

4.99 out of 5 average rating, 140 reviews

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.

Cottage in Sister Bay

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.

An open-concept living space is highlighted by a high ceiling with wooden beams. Large windows frame views of the outdoors, and a spacious sectional sofa is arranged around a coffee table atop a patterned rug. Light wood flooring complements the overall design.

4.93 out of 5 average rating, 268 reviews

Waterfront on Peaceful Moonlight Bay

Located on the shore of Moonlight Bay Lake Michigan overlooking Toft and Bues Points. Private waterfront access with beach and dock. Kayaking, canoeing, SUPs, biking, swimming, and fishing (all included). Located on a bike route near Bues Point public boat ramp, Cana Island Light House, The Ridges Sanctuary, and Baileys Harbor. Conveniently located yet private a short trip to Fish Creek/Egg Harbor (15 min), Ephraim/Sister Bay (10 min).

An aerial view captures a modern, cedar-sided house nestled among dense trees, with the expansive blue waters of North Bay visible in the background. Surrounding foliage provides a sense of seclusion and serenity, emphasizing the home's peaceful forest setting.

4.99 out of 5 average rating, 169 reviews

Winding Down - A Retreat on the "Quiet Side"

Enjoy the season and get ready to relax and recharge with family & friends. Winding Down is the perfect place to enjoy the quiet side of DC. We are walking distance from the Nature Preserve & the shores of North Bay. Located in a beautiful cedar forest that provides a needed respite. Plenty of privacy but also a short drive to Ephraim & Sister Bay. There is access to North Bay and a small public boat launch at the end of Winding Lane.

5 out of 5 average rating, 123 reviews

A cozy living room features a light grey couch adorned with navy blue pillows, paired with two beige armchairs. A round wooden coffee table is centered on a soft area rug, while large windows provide natural light and views of the surrounding greenery.

Home in Sister Bay

Cottage in Sister Bay

Beautiful + modern cottage ready for your visit! Cozy up in this private cottage during your Door County stay! Just three miles from downtown Sister Bay, Pineview Cottage is located on a serene lot nestled in the woods. A perfect place for you to unwind after your Door County adventures. If you would rather stay back, relax on our beautiful covered front and back porch or gather around the campfire with friends and family!

The exterior of the Howard House is showcased, featuring a modern design with dark siding and a metal roof. A welcoming front porch includes two chairs for relaxing, while a grassy area highlights landscaped greenery. Surrounding trees add a touch of nature to the serene setting.