Vacation rentals in Baileys Harbor

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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 favourite
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
4.96 out of 5 average rating, 110 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 favourite
The exterior of a cozy cottage is framed by lush green foliage. A white façade features a peaked roof and a small front porch with a large door. Sunlight filters through the leaves, creating a serene atmosphere in the surrounding garden.
Guesthouse in Fish Creek
4.96 out of 5 average rating, 275 reviews

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.

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, 359 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 cozy studio space is accentuated by a wooden vaulted ceiling. A spacious bed is dressed in light, patterned bedding, while a comfortable couch is positioned beside a small table. Soft lighting from a lamp and an inviting rug contribute to the warm ambiance.
Guest suite in Egg Harbor
4.95 out of 5 average rating, 299 reviews

Cozy Farmhouse Studio

The 16 X 19 foot private studio, is located on the second story of our 120 year old farmhouse and has a private entrance and drive. It is equipped with its own kitchen, bathroom, balcony, queen bed, couch and closet. Our farmhouse is located on five scenic acres adjacent to our pottery studio and gallery. Please be aware that we have no air conditioning. It usually cools off at night, so it’s not typically necessary. We have a ceiling and cooling fan for the hot days.

Guest favourite
Home in Baileys Harbor
4.99 out of 5 average rating, 123 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
Cabin in Baileys Harbor
4.77 out of 5 average rating, 311 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

Top guest favourite
The cottage showcases a distinctive A-frame design surrounded by lush greenery. A spacious wooden deck with yellow Adirondack chairs invites relaxation, while large front-facing windows allow for natural light and views of the serene wooded lot.
Cottage in Sister Bay
5 out of 5 average rating, 222 reviews

Modern A-Frame, Sister Bay, Coffee Bar, Fireplace

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
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
4.99 out of 5 average rating, 158 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.

Guest favourite
Home in Baileys Harbor
4.93 out of 5 average rating, 281 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).

Top guest favourite
Home in Baileys Harbor
4.99 out of 5 average rating, 177 reviews

Winding Down - A Retreat on the "Quiet Side"

Let it snow, let it snow, let it snow! Bring your snowshoes and cross country skies! 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.

Guest favourite
A winter scene is featured, showcasing a deck railing painted in blue and green. Snow covers the ground and decorates the railings, while the view includes bare trees shrouded in a light snowfall, creating a serene atmosphere.
Apartment in Egg Harbor
4.86 out of 5 average rating, 487 reviews

Downtown Sunset View Apartment

This sunny apartment is located in downtown Egg Harbor-walk to anywhere in town. The sunset view of the Bay of Green Bay is spectacular. Hardwood floors, skylights, w&d, soaking tub. Located above the local natural food store/cafe. This is one of 2 listings in the building- also check out my Treehouse apt. No small children pls. Dog friendly only with permission $5/night fee for dogs

Guest favourite
An inviting courtyard is featured, showcasing a charming cottage with wooden siding. String lights illuminate the space, while two chairs are positioned on wooden planks amidst gravel and greenery, creating a tranquil outdoor setting. Lush plants and flowers enhance the natural atmosphere.
Apartment in Sturgeon Bay
4.91 out of 5 average rating, 523 reviews

A City Cottage | Downtown

With the vintage charm and updated comforts of home this cozy little carriage house renovated into a city cottage will surely hold a special place in your heart. Leave your car parked and enjoy a walk around the bridge and our three shopping disticts. This unit requires stairs and is considered a tiny home. DCTZ | **3556165117** State Permit | CKRA-AB6SSC

Popular amenities for Baileys Harbor vacation rentals

Frequently Asked Questions

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

    Four-legged friends are welcome in Baileys Harbor. Choose from more than 20 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!

  • 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.

  • 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 $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • Do house rentals in Baileys Harbor have air conditioning?

    Absolutely! We offer over 10 house 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.

Quick stats about vacation rentals in Baileys Harbor

  • Total vacation rentals

    Explore 50 vacation rentals in Baileys Harbor

  • Nightly prices starting at

    Baileys Harbor vacation rentals start at $123 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 of Baileys Harbor vacation 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!

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