Holiday rentals with outdoor seating in Baileys Harbor

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Top-rated rentals with outdoor seating in Baileys Harbor

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite
The living area features warm wooden beams and a stone fireplace, creating a cozy atmosphere. Large windows provide natural light and a view of the outdoors. Comfortable seating is arranged with a sectional couch, two chairs, and a coffee table, inviting relaxation.
Cottage in Ellison Bay
4.93 out of 5 average rating, 110 reviews

Pet-Friendly, Cozy Cottage in Northern Door County

- Pet-friendly, 2 bedroom home in Northern Door County - Indoor fireplace and outdoor bonfire pit (wood provided) - Beautiful screened porch to enjoy nature - 5 minutes from famous Curvy Road, Washington Island Ferry, Newport State Park & Europe Bay Beach - Short drive to neighboring villages - Sister Bay, Ellison Bay, Baileys Harbor, etc - Walk or bike (provided) to Hedgehog Harbor - Includes all amenities to make you feel at home - Need more space? Check out our neighboring cottages next door.

Top guest favourite
A quaint cottage stands surrounded by snow-covered trees, with a light grey door and window accents visible. The structure features a simple white exterior, complemented by a winter landscape of freshly fallen snow, creating a serene and peaceful atmosphere.
Guest house in Fish Creek
4.96 out of 5 average rating, 274 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
The living area showcases a light gray couch, a round coffee table with a small plant, and a rocking chair. A flat-screen TV is positioned near a decorative cabinet. The kitchen area is visible in the background, featuring a breakfast counter with seating.
Apartment in Ephraim
4.95 out of 5 average rating, 285 reviews

Bright • Cozy • Clean • Condo Near Water • Ephraim

Our bright, clean, cozy, ground-floor condo is just a block from the water in Ephraim. There is 1 bedroom (queen) and a sleeper sofa in the living space (queen). There is a spacious bathroom with shower/tub and large vanity. Shower and toilet area are separate from sink/vanity area. Walk right out onto your own private patio which connects to our spacious yard. Full kitchen w/ stove (small oven/stove), fridge, microwave, toaster, Keurig, cookware, dishes, glassware & dishwasher.

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
4.95 out of 5 average rating, 256 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.

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, 358 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
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

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, 220 reviews

Sister Bay A-Frame | 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, 157 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).

Guest favourite
A log cabin exterior is showcased, featuring a steeply pitched roof and a large porch area. Two seating chairs are positioned near the entrance, with seasonal pumpkins placed along the front. The surrounding trees display autumn foliage against a clear blue sky.
Cabin in Sister Bay
4.95 out of 5 average rating, 128 reviews

3 Bed, 2 bath log cabin in Sister Bay w/ fire pit

Door County at its finest! Located minutes away from Sister Bay's main attractions. You can enjoy the privacy of the cabin a wooded lot with quick access to many activities in the surrounding area. 1 mile away from Northern Haus wedding venue 10 minutes drive from Peninsula State Park 20 minutes drive from Newport State Park 25 min from Whitefish Dunes State Park 20 min from ferry to Washington Island

Guest favourite
The exterior of the Howard House is showcased, featuring a modern design with dark siding and a metal roof. A welcoming front porch includes two chairs for relaxing, while a grassy area highlights landscaped greenery. Surrounding trees add a touch of nature to the serene setting.
Home in Baileys Harbor
4.92 out of 5 average rating, 199 reviews

Howard House - Downtown Baileys Harbor

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.

Popular amenities for outdoor seating rentals in Baileys Harbor

Quick stats about holiday rentals with outdoor seating in Baileys Harbor

  • Total holiday rentals

    Explore 30 holiday rentals in Baileys Harbor

  • Nightly prices starting at

    Baileys Harbor holiday rentals start at $126 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Baileys Harbor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Baileys Harbor rentals

  • 4.9 Average rating

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