Baileys Harbor vacation rentals

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Top-rated vacation rentals in Baileys Harbor

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Guest favorite

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).

Oct 6 – 13

G$34,157 GYD per night

Guest favorite

Home in Baileys Harbor

5.0 out of 5 average rating, 140 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.

Jan 15 – 22

G$70,661 GYD per night

Guest favorite

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.

May 5 – 12

G$31,857 GYD per night

Guest favorite

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 22 – 29

G$25,721 GYD per night

Guest favorite

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.

Nov 16 – 23

G$31,561 GYD per night

Guest favorite

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

G$41,863 GYD per night

Guest favorite

Home in Baileys Harbor

4.91 out of 5 average rating, 271 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

G$36,495 GYD per night

Guest favorite

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

G$98,929 GYD per night

Guest favorite

Home in Sturgeon Bay

4.94 out of 5 average rating, 135 reviews

Dock on the Bay Coach Home

Experience waterfront living in Door County in our cozy Coach Home. A perfect getaway for two, with easy access to boating, fishing, restaurants, theatres and state parks of Door County. Relax on the deck watching boats and waterfowl. We are in a residential neighborhood just off the highway, reducing your travel time and giving you more time to enjoy! Adults only. No more than 1 dog allowed, no puppies please. There is an additional fee for pets.

Oct 24 – 31

G$32,338 GYD per night

Guest favorite

Home in Baileys Harbor

4.93 out of 5 average rating, 204 reviews

Waterfront on Peaceful Moonlight Bay

Located on the shore of Moonlight Bay Lake Michigan overlooking Toft and Bues Points. Private waterfront access with beach and dock. Kayaking, canoeing, paddle boarding, biking (included) swimming, and fishing. 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 and Egg Harbor (15 min.), Ephraim and Sister Bay (10 min.)

Oct 22 – 29

G$156,296 GYD per night

Guest favorite

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

G$27,944 GYD per night

Guest favorite

Home in Sturgeon Bay

4.98 out of 5 average rating, 209 reviews

Lily Pad Cottage, Door County: Waterfront Cottage

Lily Pad is perched, on the waters of Sturgeon Bay, with a historic shipbuilding waterfront and artistic culture. A perfect romantic getaway for a couple seeking quality time in one of the last cottages on the waterfront of Sturgeon Bay. Fantastic location, close to everything on the west side of the city. Lily Pad has a deck and a fire pit in the yard! Need more space?, Eagle View Suite is a two bedroom, next door to Lily Pad Cottage.

Nov 19 – 26

G$26,131 GYD per night