Holiday rentals in Baileys Harbor

Farm stay in Baileys Harbor

4.84 out of 5 average rating, 170 reviews

Heart of the Door Homestead (Pet walking trails)

Located in Door County’s Peninsula Center with walking trails on 13 acres, great for pets, a screen shed for BBQs on the charcoal grill and a fire pit. Please add your pet guest in the guest count (a $40 one-time fee plus taxes will be applied). Please contact us for possible reduced pricing for long-term stays. 1st Floor: One bedroom (one double bed) and full bath. 2nd Floor: Three bedrooms (two double beds and two single beds) and half bath. We also have stays in Appleton & Green Bay.

4.9 out of 5 average rating, 102 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.

Guest house in Fish Creek

4.97 out of 5 average rating, 226 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.

Farm stay in Baileys Harbor

4.95 out of 5 average rating, 232 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.

4.91 out of 5 average rating, 327 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

4.99 out of 5 average rating, 112 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!

4.79 out of 5 average rating, 229 reviews

Cabin in Baileys Harbor

Bailey's Harbor Door County Cabin North Unit

Cozy 1 bedroom cabin(side by side,north unit/south unit)each with its own private yard from each other/patio secluded by trees.Featured on Travel Wisconsin!New installed AC April 2019! Private entrance.Walking distance to Kangaroo Lake and popular Door County bar.Great for all year,round,hiking,kayaking,swimming,camp fires. Hidden in the woods but a close drive to Lake Michigan side tourist part(5-10min drive). Rent one half or both if available to sleep a total of 16.

4.78 out of 5 average rating, 125 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.

5 out of 5 average rating, 188 reviews

Cottage in Sister Bay

Cozy A-Frame - Coffee Bar, Fireplace - 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.

4.98 out of 5 average rating, 128 reviews

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.

Cottage in Baileys Harbor

4.95 out of 5 average rating, 131 reviews

20% Off! 4 BR + Coffee Bar + Firepit + Disc Golf

May & June Sale! Book now and save 20% on remaining May & June dates—perfect for families, couples, or a quiet Door County escape! Pull off the highway to the charm of a century-old, lovingly restored cottage just minutes from downtown in the heart of Door County. Stonewall Cottage blends historic character with modern comfort, offering a peaceful escape for families, couples, or friends.

4.93 out of 5 average rating, 191 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.

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Other great holiday rentals in Baileys Harbor

4.94 out of 5 average rating, 65 reviews

Charming Cottage set on 5 Country Acres

KristinRating, 5 stars7 months ago

This was the cutest place for my family. It was super private and my daughter loved to play in the loft area! The games were definitely a hit! We had a little hiccup during check in when the cleaning service was running behind. But Michelle was very accommodating for the hiccup and fast to respond. Other than that, we had a great time and loved everything about the house. From the inside cozy decor, to the trails outside, we would definitely stay here again!

4.96 out of 5 average rating, 26 reviews

Cabin in Sister Bay

Waterfront A-frame: Vintage Charm, Modern Comfort

KateRating, 5 stars1 month ago

Such a beautiful cabin on a protected bay of Lake Michigan but still see enough to feel the big water and hear the waves crashing. Awesome fire place great place to sit and read and relax by the fire. Lots to do nearby, if you want to leave. The hosts are excellent and welcoming. Would love to go back! Pet friendly is a plus.

Cottage in Baileys Harbor

5 out of 5 average rating, 15 reviews

Amazing House, Amazing Garden, Downtown

TylerRating, 5 stars11 months ago

Martina’s house was very clean, comfortable and well-furnished. The gardens are spectacular! Bailey’s Harbor is a great little town and the house is a 30 second walk from the main street, as well as the lake. Great spot for those looking for a Door County getaway.

5 out of 5 average rating, 45 reviews

Cabin in Baileys Harbor

Cedarwood Cabin / Centrally Located Comfort

HannahRating, 5 stars2 weeks ago

This was truly one of the best Airbnb's I've ever stayed at. It was the perfect relaxing and cozy set up for our girls weekend over Memorial Day weekend. Highlights were definitely the endless streaming services for our movie nights, Smores fixings for days, and the most amazing scones frozen and ready for us to bake in the morning. I would recommend this property to everyone and anyone. The location was perfect proximity to all things Door County and even was walking distance to a cozy local watering hole for those who love a good local "dive" bar. Cannot thank Diane enough for hosting our group!

Guest house in Egg Harbor

4.98 out of 5 average rating, 51 reviews

Village Tree House, chill setting walkable to town

AllisonRating, 5 stars6 days ago

This place was so cute and adorable. The furnishings and design were very well thought out and went together perfectly. It was very easy to find and get in with the automatic lock. It wasn’t super private being on the same lot of the main house and another cottage. We didn’t hear the neighbors or anything so it was still quiet. It had everything that was needed for two people. There just wasn’t a closet, and some hangers would’ve been nice to hang up clothes. Or an optional clothing rack. But would definitely recommend and stay here again. It was very close to shops, restaurants and winery’s.

Loft in Baileys Harbor

4.87 out of 5 average rating, 79 reviews

Stunning Studio in Baileys Harbor, Muirfield Flat

WilliamRating, 5 stars10 months ago

This flat is very quiet, the main house may have been occupied but we could rarely tell. The king bed was comfortable. The skylights in the kitchen are surprisingly bright and help make the flat brighter throughout the day as the main window faces east. The tree frogs that hung around the flowerbeds were entertaining to spot every time we entered and exited. This is a second story flat partially above a garage. It seemed like a story and a half of steps to enter. We never heard any car or garage door noise.

5 out of 5 average rating, 3 reviews

Loft in Ephraim

Arbor Cottage Loft

AnnisonRating, 5 stars6 days ago

This place is beyond great! The hosts were very friendly and welcoming. I had never been to Door County before and wanted a place that was smaller, but had enough things to do by it. It has amazing views, the sunsets were beautiful. We drove to Sister Bay to grab food and such, but there are great places that are walkable from here! I will say the road noise is a bit loud in the day time, but other than that it was amazing. I will recommend this place over and over again to people!