Holiday rentals in Baileys Harbor

Lakefront Cottage · Sand Beach · Waterfront Deck

Welcome to Sandvik House, a Scandinavian-inspired, lakefront retreat nestled along the Lake Michigan shore. This spacious home is an ideal place for families, couples, or friends looking for an effortless Door County getaway. One of the standout features of this property is the sandy beach right out your back door. Build sandcastles with the kids, stroll along the shore, or kayak over to Cave Point County Park. Centrally located on the Door Peninsula, neighboring towns are a short drive away!

Fun for All Ages: Game Room, Screen Porch, Firepit

Welcome to Chicory Cottage, a private retreat in the heart of Door County, just a short walk from Kangaroo Lake. Enjoy a cozy indoor fireplace, a spacious primary suite, a relaxing screen room, and a fun-filled game room for all ages. Lounge in recliners, spin vinyl records, sip wine by the fire table, or cozy up for a bonfire under the stars. Like all of our properties at ChicoryDoorCounty, every detail is thoughtfully designed to offer comfort, connection, and a true Door County experience.

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

♦♦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!

Lakeside Cottage on the Bluff

Surrounded by woods and crystal clear water, Nordcliff Cottage is a minimalist retreat perched above Lake Michigan, with sweeping views of Washington, Plum, and Pilot Islands. Built in the 1960s, and equipped with modern furnishings and decor, this Scandinavian-inspired cottage offers a serene, calming space where natural light floods the open loft, inviting relaxation and connection with the tranquil lakeside setting. A sand beach with public access is just steps away.

Baileys Harbor Condo, 3 BR, 2.5 Bath, Door County

Not your usual Door County condo. This is one of only 6 condo units in this building adjacent to Maxwelton Braes golf course. The condo has a private entrance with two floors, laundry room and two covered decks. No through street and not a busy resort -- just a quiet get away. A spacious, well maintained and tastefully decorated three bedroom, 2.5 bath condo in Baileys Harbor with lots of living space and sunny rooms. Minutes from Baileys Harbor, parks and beaches.

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!

Moonlight Cabin located in Baileys Harbor

Moonlight Cabin, Just bring your suitcase and enjoy all the comforts of home. This home is 4 bedrooms, 2 baths, open concept kitchen/ dining/ living room and 4 season sunroom is the perfect spot for a getaway! You can also relax in the private backyard sitting around the campfire or grilling out on the front deck. Located walking or biking distance to downtown you can enjoy everything Baileys Harbor has to offer from restaurants, brewery, waterfront, and much more.

2 Bed A-Frame, Fire Pit, Coffee Bar - Sister Bay

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.

Cozy Cottage on a Rock Bluff Overlooking Lake MI

Baileys on the Rocks "Rockledge" Cottage is a private historic cottage located on a small rock bluff in Baileys Harbor, Wisconsin in beautiful Door County. Situated on a wooded lot and directly across the street from Lake Michigan, you'll find it hard to believe you are in the village of Baileys Harbor and within walking distance of its popular beaches, harbor, restaurants and quaint shops. *Cleaning Procedures Meet or Exceed CDC Guidelines*

Waterfront on Peaceful Moonlight Bay-NEW SAUNA

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).