Vacation rentals in Baileys Harbor

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Top-rated vacation rentals in Baileys Harbor

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Guest favourite

Home in Baileys Harbor

5.0 out of 5 average rating, 28 reviews

Tucked Away Ranch in the Woods ~ Mins to Harbor

Step into the rustic and modern 3BR 2Bath getaway 5mins from the center of Baileys Harbor, WI. It offers a relaxing oasis and an escape from the everyday hustle and bustle. Start your day with a cup of coffee by the fireplace, then set out to explore the picturesque Door County. The stylish design and rich amenity list will leave you in awe. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Smart TV ✔ Fireplace ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Free Parking See more below!

Mar. 9 – 16

$441 CAD per night

Guest favourite

Apartment in Fish Creek

4.98 out of 5 average rating, 198 reviews

Night Cap Studio Loft in Downtown Fish Creek

In the heart of Fish Creek, above our bustling Hat Head shop, enjoy your stay in our newly remodeled second story studio loft. Complete with studio bedroom, bath, kitchen with new appliances, sitting room, and private balcony deck. Enjoy walking distance to the beach, shops, restaurants, Peninsula State Park, and more. Close to the action, yet a great hideaway for privacy and relaxation. Bright and cheery, modern, simply stated, and clean. For adult single or couple. (Sorry no pets or kids).

Sep. 25 – Oct. 2

$271 CAD per night

Guest favourite

Home in Baileys Harbor

5.0 out of 5 average rating, 141 reviews

Winding Down - A Retreat on the "Quiet Side"

From quirky games and parades to chocolates, chili and icy sculptures, the Peninsula plays host to festivals and special events throughout the winter. 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. Enjoy cross country skiing OR snowshoeing in the trails nearby. Come in from the cold to build a cozy fire & enjoy a glass of wine.

Feb. 26 – Mar. 5

$581 CAD per night

Guest favourite

Guesthouse in Fish Creek

4.97 out of 5 average rating, 156 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.

Feb. 10 – 17

$390 CAD per night

Guest favourite

Apartment in Sturgeon Bay

4.94 out of 5 average rating, 112 reviews

Door Room

This unique 1-bedroom upper apartment is part of a four-unit apartment building. The upper level has two Airbnb apartments. The Door Room is located in the heart of historic downtown Sturgeon Bay and within walking distance of all the action! It was creatively decorated with "subtle" school-themed touches that just may remind you of a dorm room (minus the ramen and bunk beds!) The Door Room is located on a quiet street in an older neighborhood. You also have your own private deck.

Nov. 12 – 19

$203 CAD per night

Guest favourite

Cottage in Sturgeon Bay

4.87 out of 5 average rating, 187 reviews

Jacksonport Lake Park Cottage

Quiet home snuggled in the heart of Jacksonport, situated along Lakeside Park on beautiful Lake Michigan. Our spacious home has been renovated with new flooring, countertops, windows in the sun porch (beautiful lake views), and gas fireplace. With 3 bedrooms, and loft with day bed you can sleep 7 comfortably. The home has a large yard for lawn games, sand volleyball court, and is only 100' from lakeside beach which has a sugar sand swimming beach, and a large playground for kids.

Dec. 9 – 16

$243 CAD per night

Guest favourite

Condo in Ephraim

4.93 out of 5 average rating, 202 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.

Dec. 2 – 9

$243 CAD per night

Guest favourite

Farm stay in Baileys Harbor

4.95 out of 5 average rating, 206 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.

May 28 – Jun. 4

$336 CAD per night

Guest favourite

Guesthouse in Baileys Harbor

4.93 out of 5 average rating, 28 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!

Dec. 7 – 14

$262 CAD per night

Guest favourite

Cottage in Baileys Harbor

4.96 out of 5 average rating, 170 reviews

South Lane Cottage #1

This sweet 2 bedroom, 1 bath home, with a glimpse of Lake Michigan from the living room window. This location is in pristine condition, and has a newly remodeled kitchen. As well as a large Trex deck at the rear of the house. You can also take advantage of the short walk to Anclam park and waterfront fun, or the shops and restaurants in downtown Baileys Harbor. This is the second listing from the owners of Bearded Heart Coffee, which is located just down the road.

Sep. 29 – Oct. 6

$753 CAD per night

Guest favourite

Guesthouse in Baileys Harbor

4.94 out of 5 average rating, 18 reviews

Rustic Beach House

Welcome to our quaint, 3 seasons lakefront cottage! It was built in the 50’s and has the simple charm of an old cabin. There are no bells and whistles…but it has the necessary amenities for a peaceful stay. You are directly on a white sand beach of Lake Michigan. It’s just north of Jacksonport and about a 15 minute drive to most anywhere in Door County. With 1 bedroom plus a trundle bed and a pull out couch it’d be perfect for a small family or a couple.

Sep. 12 – 19

$404 CAD per night

Guest favourite

Cottage in Sturgeon Bay

4.97 out of 5 average rating, 302 reviews

Sturgeon Bay Waterfront Cottage, Private beach.

Waterfront guest cottage on Door County's Gold Coast! Nestled among luxury homes, this quaint 1930's cottage has undergone an interior renovation while preserving its character on the outside. Two bedroom, one full bath, stocked kitchen, living room. Located steps from the bay with a private beach. Hear the gentle sound of waves lapping on the shore as you sleep. Bring your kayak and fishing poles. Perfect for anyone seeking a quiet retreat!

May 5 – 12

$240 CAD per night