Vacation rentals with outdoor seating in Baileys Harbor

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.

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.

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.

♦♦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!

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.

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.

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.

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!

Howard House - Downtown Baileys Harbor

The Howard House is a freshly renovated vacation rental located in the heart of downtown Baileys Harbor, Door County, Wisconsin. Clean, modern, comfortable. This 2-bedroom, 2-bathroom house includes a fully outfitted kitchen, comfortable living space, private backyard and is located within walking distance of Door County Brewing, Chives Restaurant and the rest of Downtown Baileys Harbor.