Vacation rentals in Baileys Harbor

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Quick stats about vacation rentals in Baileys Harbor

  • Total vacation rentals

    Explore 70 vacation rentals in Baileys Harbor

  • Nightly prices starting at

    Baileys Harbor vacation rentals start at G$20,916 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,340 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Baileys Harbor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Baileys Harbor rentals

  • 4.9 Average rating

    Baileys Harbor stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Baileys Harbor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Baileys Harbor
5.0 out of 5 average rating, 76 reviews

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!

Top guest favorite
A modern cottage exterior is shown, featuring dark blue siding and white trim. A welcoming entrance is highlighted by a wooden awning supported by brackets. Two flower pots hang from the awning, and a small garden borders the stone path leading to the front door.
Home in Sturgeon Bay
4.97 out of 5 average rating, 131 reviews

Cave Point Retreat

Kick back and relax in this calm, stylish space. Located 1.5 miles from the famous Cave Point attraction in White Fish Dunes State Park, our cottage has everything you need for a fun, relaxing, and peaceful stay. Located 15-20 minutes from every major town in the County: Baileys Harbor, Egg Harbor, Sturgeon Bay, Fish Creek, and Sister Bay. Our space is brand new construction in 2024 finished with stained concrete floors, electric fireplace, upscale finishes, large back patio, & shared sauna.

Top guest favorite
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.
Home in Baileys Harbor
4.92 out of 5 average rating, 382 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

Top guest favorite
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.
Farm stay in Baileys Harbor
4.96 out of 5 average rating, 269 reviews

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.

Guest favorite
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.
Home in Baileys Harbor
4.99 out of 5 average rating, 131 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!

Guest favorite
Cabin in Baileys Harbor
4.78 out of 5 average rating, 324 reviews

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

Guest favorite
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
4.99 out of 5 average rating, 119 reviews

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.

Top guest favorite
The exterior of the condo is showcased with well-maintained landscaping, featuring lush green grass and mature trees. A two-car garage with a white door is visible, alongside a stone facade that adds texture to the home. Large windows allow natural light to fill the interior.
Townhouse in Baileys Harbor
4.9 out of 5 average rating, 78 reviews

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.

Top guest favorite
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.
Guesthouse in Baileys Harbor
4.97 out of 5 average rating, 92 reviews

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!

Top guest favorite
Cottage in Sister Bay
5.0 out of 5 average rating, 243 reviews

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.

Top guest favorite
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
4.98 out of 5 average rating, 179 reviews

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.

Top guest favorite
A white cottage with green shutters is set among lush trees, presenting a welcoming entrance with a gabled roof and a central door. Natural light filters through the surrounding foliage, highlighting the cottage's simple yet charming exterior.
Home in Baileys Harbor
5.0 out of 5 average rating, 42 reviews

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*

Popular amenities for Baileys Harbor vacation rentals

When is the best time to visit Baileys Harbor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,831 GYDG$41,831 GYDG$37,648 GYDG$28,027 GYDG$36,602 GYDG$44,969 GYDG$56,263 GYDG$53,335 GYDG$42,877 GYDG$39,530 GYDG$34,302 GYDG$42,877 GYD
Avg. temp-8°C-6°C0°C7°C14°C19°C21°C20°C16°C9°C2°C-4°C

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Baileys Harbor?

    Four-legged friends are welcome in Baileys Harbor. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Baileys Harbor?

    Yes! Work meets play with ease at over 10 vacation rentals in Baileys Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Baileys Harbor vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Baileys Harbor, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Baileys Harbor?

    Baileys Harbor has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Baileys Harbor?

    Experience the best of Baileys Harbor with our house rentals, starting at about $340 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cabin rentals in Baileys Harbor have air conditioning?

    Absolutely! We offer over 10 cabin rentals with air conditioning in Baileys Harbor. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Baileys Harbor have wifi?

    Absolutely! We offer over 20 boutique hotel rentals with wifi in Baileys Harbor. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Baileys Harbor have a bbq area?

    Absolutely! We offer over 20 hotel rentals with a bbq area in Baileys Harbor. Enjoy a tailored experience with all the comforts you desire.