Holiday rentals 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.

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.

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

Bailey's Harbor Door County Cabin North Unit

Cozy 1 bedroom cabin(side by side,north unit/south unit)each with its own private yard from each other/patio secluded by trees.Featured on Travel Wisconsin!New installed AC April 2019! Private entrance.Walking distance to Kangaroo Lake and popular Door County bar.Great for all year,round,hiking,kayaking,swimming,camp fires. Hidden in the woods but a close drive to Lake Michigan side tourist part(5-10min drive). Rent one half or both if available to sleep a total of 16.

Lighthouse Lookout

Welcome to our spacious 1 bedroom guesthouse in the heart of downtown Baileys Harbor. With stunning views overlooking the sparkling waters of Lake Michigan, you'll be immersed in the charm of this vibrant community. Inside, you'll find a full kitchen, king size organic mattress, washer dryer, and pull-out loveseat, making it the perfect retreat for couples or small families. Come stay with us and experience the ultimate in comfort, convenience, and beautiful scenery!

Cozy A-Frame - Coffee Bar, 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.

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.