Holiday rentals with outdoor seating in Baileys Harbor

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.

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

Door County Dreaming Cabin, Pet Friendly

Tastefully updated cottage with in walking distance to downtown Bailey's Harbor. Explore beaches, state parks, snowmobile trail, Ridge's Sanctuary, restaurants, bars, and local brewery! Our Door County Cottage is perfect for your next getaway and Its so cute and cozy! Great back yard to gill out in and have a fire in the fire pit! Also check out our fresh basil garden! We want to be your guide while you enjoy our amazing town and cozy cottage! Sleeps up to 6, and 1 pet

Mid Century Lake House with private beach

Come enjoy Door County in this beautiful lake house. Completely renovated with private beach access this is the perfect place to relax. Everything in this home is brand new! Conveniently located next to Ellison Bay & Sister Bay, enjoy all the hustle and bustle of Door County and retreat back to the serenity of the house Swim in the lake, paddle board, or take one of our bicycles and enjoy the scenery. Enjoy the winter snow shoeing, cross country skiing or snowmobiling.

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 fall & winter season! 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 at the small public boat launch at the end of Winding Lane.

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).

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.

The Loft | Walkable Egg Harbor Retreat w/ Style

Welcome to The Loft — a bright and private second-floor retreat in the heart of Egg Harbor! • Upscale 2-bedroom, 2-bath retreat • Renovated in 2022 with modern comforts • Steps from shops and dining on Highway 42 • Pet-friendly (up to 2 dogs) — $75 fee only if bringing pets