Holiday rentals in Baileys Harbor

Serene, cozy cottage in the woods

Welcome to your safe Haven in the woods! Located conveniently in Sturgeon Bay one block from the lake, this cozy cottage will not disappoint! Sipping coffee on the inviting front porch, getting comfy around the grand fireplace or creating a delicious dinner in the modern kitchen will have you feeling right at home! Haven offers plenty of space for families to get together and create lasting memories. Even a bunk room above the garage gives the kids their own hang out space. Close to all the fun!

DoorCo Happy Place @Landmark Resort

Welcome to this wonderful, full of positive energy and relaxing resort! The condo is a great place to relax, explore and rejuvenate! 1 bedroom with a queen size bed and queen sleeper sofa in the living room and fully equipped kitchen make enough room for 4 guests. The resort is a great place to enjoy- 1 indoor pool, exercise room and a game room located in the main building, hot tub, sauna in each building, 3 HEATED outdoor pools open seasonally (May- August), tennis court, playground, a trail.

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.

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

Winding Down - A Retreat on the "Quiet Side"

Enjoy the fall & winter season! We still have availability for the up coming Christkindlmarket in Sister Bay & Fish Creek Winterfest in January. 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.

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.

Historic Log Cabin by the Bay (Lake View)

"Doc's Hideaway" sits at the tip of the Door County peninsula in beautiful Gills Rock, surrounded by lush woods on one side and the picturesque Bay and bluffs on the other. This historic mid-1800’s cabin has been lovingly renovated (admire the character of the original hand scraped wood walls and ceiling beams) with all the amenities and comforts of home. New in 2022: extra fast Wifi via Starlink (up to 105 mbps) and a high efficiency ductless AC and heating system.

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.

Baileys Harbor Yellow Home with a View

Situated in the heart of down town Baileys Harbor, Wisconsin. You can sit in the kitchen and see Lake Michigan as you drink your morning coffee. No need to drive if you do not want to, you have restaurants, bars and shops all within walking distance. You have the whole house to yourself, but we own a coffee shop one building over, in case you need anything. The house is a late 1920's house, but newly upgraded, with a new kitchen and bathroom.

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.