Holiday rentals in Baileys Harbor

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Quick stats about holiday rentals in Baileys Harbor

  • Total holiday rentals

    Explore 70 holiday rentals in Baileys Harbor

  • Nightly prices starting at

    Baileys Harbor holiday rentals start at €86 per night before taxes and fees

  • Verified guest reviews

    Over 3,340 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    70 of Baileys Harbor holiday rentals include wifi 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 holiday rentals in Baileys Harbor

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

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Top guest favourite
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!

Guest favourite
The open-concept kitchen and dining area features green cabinetry and stainless steel appliances. A round braided rug is placed under the dining table, surrounded by modern chairs. Natural light fills the space, highlighting the adjacent living area with comfortable seating and decorative accents.
Home in Baileys Harbor
4.91 out of 5 average rating, 153 reviews

Cozy & Relaxing Wooded Home; Close to Everything!

Relax with the family at this quiet, spacious, and secluded 3 bedroom, 1.5 bath home. Just up the road from Lake Michigan and charming downtown Bailey's Harbor, our central location makes it a breeze to visit all of Door County - Sister Bay, Fish Creek, and Ephraim are all just minutes away. Hikers will enjoy the nearby Ridges Sanctuary, Toft Point, and more. This property allows for proximity to all of the fun, while allowing a tranquil and quiet place to stay and relax while on vacation.

Top guest favourite
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, 387 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 favourite
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, 273 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.

Superhost
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, 132 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 favourite
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, 123 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.

Superhost
Home in Baileys Harbor
4.78 out of 5 average rating, 160 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.

Superhost
Cottage in Sister Bay
5.0 out of 5 average rating, 246 reviews

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

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 favourite
Home in Baileys Harbor
4.94 out of 5 average rating, 299 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).

Guest favourite
Home in Baileys Harbor
4.91 out of 5 average rating, 211 reviews

Downtown Baileys Harbor Retreat · Walk to Dining

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.

Top guest favourite
A two-story farmhouse is nestled in a lush green landscape, surrounded by trees. The structure features a light blue exterior and a welcoming front porch. A gravel path leads up to the house, providing access from the nearby road.
Farm stay in Baileys Harbor
4.86 out of 5 average rating, 206 reviews

Heart of the Door Homestead (Walking Trails)

Located in Door County’s Peninsula Center with walking trails on 13 acres, a screen shed for BBQs on the charcoal grill and a fire pit. Please contact us for possible reduced pricing for long-term stays. 1st Floor: One bedroom (one queen bed) and full bath. 2nd Floor: Three bedrooms (two queen beds and two single beds) and half bath. We also have stays in Appleton & Green Bay.

Top guest favourite
Home in Baileys Harbor
4.94 out of 5 average rating, 103 reviews

Quiet 3 bedroom wooded home in Baileys Harbor

Relaxing Baileys Harbor getaway! Just a 1-mile easy walk to the heart of town: brewery, shops, and restaurants. Perfect for couples/small families + dogs. Enjoy quiet evenings with a bonfire or Netflix. Features: full kitchen (seats 6), bedding, towels, games/puzzles provided . Personal toiletries not provided.

Popular amenities for Baileys Harbor holiday rentals

When is the best time to visit Baileys Harbor?

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Avg. price€172€172€154€115€150€184€231€219€176€162€141€176
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 cabin rentals in Baileys Harbor?

    Experience the best of Baileys Harbor with our cabin rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do boutique hotel rentals in Baileys Harbor have air conditioning?

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

  • Do cabin rentals in Baileys Harbor have wifi?

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

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

    Absolutely! We offer over 10 house rentals with a bbq area in Baileys Harbor. Enjoy a tailored experience with all the comforts you desire.