Family-friendly vacation rentals in Baileys Harbor

4.93 out of 5 average rating, 161 reviews

A serene lakeshore scene displays calm waters reflecting a clear blue sky. Gentle ripples move across the surface, while lush greenery frames the shoreline. A small boat is anchored nearby, offering a glimpse of leisure amidst the natural beauty. Rocky edges and smooth stones are present along the water's edge.

Cottage in Sister Bay

Sea Glass Cottage

Welcome to Sea Glass Cottage. Your Door County home away from home. This light and airy cottage is on the water with rock beach, beautiful sunrises, great room with beam ceilings & wood burning fireplace, kitchen ready for cooking and baking. A view of Lake Michigan from nearly every room. Perfect location for families or couples vacation. This cottage is tucked away on a wooded lot with an open backyard to enjoy sunshine and shoreline, or take a quick 5 minute drive to downtown Sister Bay.

Indoor spacesFamilyPets

Farm stay in Baileys Harbor

A wide view of the farm landscape features golden grasses swaying in the breeze, with two large silos visible in the distance. Various farm buildings are spread out under a clear blue sky, framed by trees displaying autumn colors.

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.

KitchenIndoor spacesBeach

4.96 out of 5 average rating, 279 reviews

A spacious wooden deck overlooks the tranquil waters of Lake Michigan, featuring a round table surrounded by black metal chairs. Long benches line the edges, offering additional seating. Lush greenery can be seen along the shoreline, enhancing the serene atmosphere.

4.92 out of 5 average rating, 389 reviews

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

FamilyKitchenView

A spacious living area is highlighted by a variety of seating options, including a beige sofa, a red armchair, and a classic wooden accent table. Natural light filters through windows, illuminating the colorful area rug and wooden floor, while decorative wall elements add charm to the space.

4.99 out of 5 average rating, 134 reviews

♦♦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!

KitchenFamilyAmenities

A charming log cabin is set amidst a wooded landscape, featuring a spacious screened-in porch with inviting seating options. A grill is positioned nearby, and vibrant red chairs are situated on the gravel path, surrounded by lush greenery.

4.92 out of 5 average rating, 106 reviews

Door County Cabin in the Woods, Baileys Harbor

This lovely Door County log cabin is a beautiful home located in the town of Baileys Harbor, Wisconsin. It sits on 3-1/2 wooded acres in a secluded, but not remote location. It is a perfect spot to relax, rewind and still be within minutes of all Door County has to offer. Pet friendly, open year round. Because we are pet and people friendly, we use Mosquito Squad to keep mosquitoes and ticks down to a bare minimum. Always pet & people friendly natural chemicals used.

Indoor spacesKitchenQuiet

4.99 out of 5 average rating, 125 reviews

A bright living space features modern furnishings arranged for comfort. Large glass doors provide a view of the lake and outdoor deck. Natural light fills the room, highlighting the soft area rug and contemporary chairs.

Home in Ellison 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.

KitchenFamilyNearby

Guesthouse in Baileys Harbor

A cozy living area is presented with a striped loveseat, complemented by a bright yellow pillow. A wooden coffee table sits centrally with a small decorative item. Large windows adorned with light blue curtains offer views of the surroundings and allow natural light to fill the space.

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!

KitchenFamilyGetting around

4.97 out of 5 average rating, 99 reviews

Superhost

4.78 out of 5 average rating, 162 reviews

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.

FamilyKitchenLayout

5.0 out of 5 average rating, 247 reviews

Cottage in Sister Bay

A-Frame Cottage, Fire Pit, Coffee Bar, 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.

FamilyIndoor spacesValue

4.98 out of 5 average rating, 188 reviews

A cozy cottage is nestled among tall trees, showcasing a white exterior with a stone chimney. The spacious porch features blue chairs, inviting relaxation. Lush green grass surrounds the home, complementing the peaceful rural setting.

Cottage in Sister Bay

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.

KitchenFamilyAir conditioning

4.94 out of 5 average rating, 300 reviews

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).

Indoor spacesFamilyHiking