According to a census conducted in the year 2000 (a while ago, I know) Bailey’s Harbor had just over 1000 people calling it home. This number, certainly, has gone up since then, but what remains intact is the fact that this destination is still Wisconsin’s closely guarded secret. A secluded locality, this little gem is an enchanting destination that effortlessly charms its visitors. With a vast beachside real estate not to mention the acres upon acres of green space, Bailey’s Harbor is where weary city dwellers escape to when they feel overwhelmed by life’s daily bustles. Only a few outside of Wisconsin actually consider Bailey’s Harbor as an apt vacation spot, but that doesn’t mean that you shouldn’t take it seriously. If you love nature in its most pristine form, and the serenity of seclusion appeals to you, then your search for a place to escape to is over. To help you out, we’ve compiled a list of the best Vrbo vacation rentals in Bailey’s Harbor below, so scroll down to find out more.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Beautiful house with an amazing garden (from USD 625)
Look no further for your next grand family vacation, and book yourself into Carraig Mór, one of the flagship properties at Door County Stay Suite of Homes. Newly decorated and renovated, you can find modern furnishing with granite countertops and stainless steel appliances found all over the house. The star of the place, though, is the picturesque one-acre botanical garden found in your back yard, where you can have all your family fun. It has a spacious lawn area and a large oak tree, where the kids can play with the tire swing. It is home to hundreds of flower species, which adds to the garden’s beauty. There’s also a wrap-around porch at the back to view this beautiful garden. What more are you waiting for? Book this place for your next family vacation!
Top guest reviews
Amenities & Room:
2 of the bedrooms had views of the lakeAnother much larger living room overlooks the gardensThe spacious kitchen opens onto the dining area which has a cozy living room off to the sideHaving an R/O water source in the kitchen is great; the water is refreshingly coldis remarkably easy because the kitchen island provides ample space for people to be on any side and still not interfere with the main chef -- whether they are helping prepare the meal or enjoying ...Cleanliness:
The house is decorated so beautifully and was very cleanIt was very clean and welcomingVery clean spacious and comfortable homeThey are lovingly and carefully maintained and provide privacy and quietThe house is clean and very well prepared to move inHost:
Great owners very respnsive and friendly Would definitely recommend and book againWe did have to pay extra for linensMartina (the owner) was so gracious and accommodating and helped us make this last minute trip feel like onShe made sure we knew everything we needed to and even gave us a late checkout because she also knew we wanted to get every moment out of our rare few days of vacationWhat a great and interesting guyRead more reviewsLocation:
The grounds are spectacular - I live near the Chicago Botanic Garden in Glencoe and the gardens around this house are at least as spectacularThe location of this house is wonderful with easy access and within walking distance to many restaurantsThe location is ideal for easily getting to all of the great DC activitiesThe cottage and its grounds are just beautifulAnd of course be near the Lake
2. Peaceful lodge surrounded by nature (from USD 260)
Have you ever wanted to live in a peaceful lodge with pine trees that can be seen as far as you can see, away from civilization? Well, look no further, as this accommodation just might be the “cabin in the woods” dream house you’ve been looking for! Secluded from the rest of the town, you’ll find your much-needed peace and relaxation here. The lodge is designed like an actual cabin, with wooden furnishings decorated throughout the interiors of the place. The place also features a spacious loft area, and a skylight to fully immerse yourself in nature! Come and live your cabin dreams here.
Top guest reviews
Amenities & Room:
The air conditioner could not be controlled manuallySuch a comfortable bed and OHThe cabin is large and spacious Loved the shower Enjoyed coffee in the deck in the morningeverything you might need is readily availableThe ceiling fans are not situated over the beds therefore no relief even under the fansCleanliness:
The house was very clean and just as it was describedIt was also very clean and well organizedThe cabin is very cleanThe cabin was clean and very well maintainedit is beautiful exceptionally clean and very cozyHost:
He gave good info about the area and things to do Outside of making sure we arrived at the property and reminding us of checkout proceduresHe said he lowered the tempThe owner Rick is responsive and easy to work withThe owner was very responsive and helpfuland he responded promptly and helped us resolve things quicklyRead more reviewsLocation:
drive to pretty much everywhere in Door County but perfectly out of the commotion of downtownI rented this cabin for my uncle aunt and parents; they loved itWe refilled it several times Great location for a winter escape and would be perfect for a summer one Thanks RickThey loved the upstairs loft and bunk bedsThe location is an easy drive from many wonderful activities and attractions and we really enjoyed our stay
3. Homey ranch-style cottage with large lawn (from USD 475)
Nestled on a half-acre of lawn, the Carraig Beag is a three-bedroom cottage that makes you feel like this place is your home away from home. The Carraig Beag is a ranch-style cottage, with no stairs to gain access to the rooms, and is designed with homey furniture, all in an effort to create a second home for you. Outside, there is a large lawn where you can relax on the sun loungers, or have a barbecue party with the provided grill with your friends and family. By the end of this trip, you’ll want to make this your actual home!
Top guest reviews
Amenities & Room:
The pictures do not do itIt was our first time visiting Door CountyThe cottage is well stocked and very comfortableIt is a modern clean and charming home that was very comfortable for our family of 6We had plenty of roomCleanliness:
The house was very clean and comfortable with great furnishingsThe house is a great size and is lovely and cleanThe house was great - very clean and set up perfectly for our familywe were surprised how walkable it was to everything we normally do and see in Baileys HarborHost:
Martina was great to work with and obviously cares about the property her family rents outit's furnished with care and well maintainedthe owner was a pleasure to work withAll in all a very clean very nicely decorated homethe property owner and manager was fantasticRead more reviewsLocation:
A fun local brewery is also within very close walking distance plus the many wineries in the areaThe house is nicely locatedThe restaurants we very good and close enough to walk toThe house is located conveniently in the middle of Door CountyThere's a great playground across the road and some great restaurants in the area
4. Cabin in the woods (from USD 195)
Immerse yourself in Mother Nature, and find yourself in this secluded cabin found amongst the trees where you’ll be able to go back to simple living, away from all the noise and distractions of society. Here, you’ll be able to surround yourself with the restful views and sights of nature, as the place provides you with a skylight to enjoy the stars, a fire pit for those cool evenings, and screened-in porches for total immersion in the wilderness. Rejuvenate yourself with this cabin as it allows you to experience the best of what Mother Nature has to offer!
Top guest reviews
Amenities & Room:
The cabin was so cozyThe cabin is nice and cozy with lots of amenitiesThis cabin was cozy and quietNot one but two screened in porches to watch the deer turkeys and even a bobcat walking down the drivewayI loved that there were porches off the bedroomsCleanliness:
the bedrooms were both very clean and the beds very comfortableThe cabin was very clean and well laid outand they really did try to think of everything their guests might needHost:
Karen was wonderful to work with and so very helpful setting things upMy wife and I both celebrated our February birthdays with a winter weekend adventure in Door CountyThere is also a wrap around deck as wellThe real fireplace was a large draw for us and those staffing this location had it all set up and ready for us when we arrived so that all we had to do was light the firebut when we wanted to venture out we were close to townRead more reviewsLocation:
The neighbors are just close enoughQuiet location and easy to get to either side from itbut just distant enough to still haveWe stayed in late March and there was still lots of snow and ice on the groundand you are within 15 minutes of other spots on the western side of the penninsula
5. Nautical-themed cottage with view of the lake (from USD 449)
Enjoy this nautical-themed cottage, where it really makes you feel as if you’re living by the sea! With iconic decorations sprawled throughout the house, you’ll definitely enjoy the well-thought-out decoration featured in the house. And of course, just outside, you’ll be able to enjoy the views of the lake on a newly built flagship stone patio, where you can have your morning coffee or your evening drink. What a classic way to experience Lake Michigan!
Top guest reviews
Amenities & Room:
The beds were so comfortable we all slept great with the windows open and the fresh night airYou do not need a car to get anywhere in townThe accommodations were state-of-the-artthe fans cool during the warm week fantastic kitchen perfect porch to watch the town wake up and go to bedBe aware if small children that you need paint sticks to keep certain old windows openCleanliness:
The house was so clean and spaciousHouse was clean and well furnishedThe dishwasher full kitchen and full sized washer and dryer were perfect tooThe house is meticulously cleanThere were plenty of clean towelsHost:
great beer and most importantlycoffee houses and shops that Baileys Harbor has to offer Easy parking Helpful Door County tips and recommendations from the ownerPam was a wonderful and gracious hostThe Ridges farmers market and the marinacozy and the host Pam is very responsive and friendly I would absolutely recommend staying here to anyone visiting Door CountyRead more reviewsLocation:
The house is in a great downtown locationAnd the place is located moments from everything we loved in Baileys HarborWe enjoyed walking to the breweryGreat location walkable to all the best restaurants barsThis property has the most amazing location right in town and walking distance to amazing restaurants
6. Century-old farmhouse (from USD 412)
This newly renovated century-old town farmhouse brings you back to a simpler time, where you simply enjoy company with each other or enjoy nature itself as you can lounge around and take the serenity of the world. With four bedrooms, the place is best enjoyed with friends and family, as there is also a large lawn at the back to laze around or have picnics and activities with your loved ones. The house is also built over old apple orchards and gardens, which adds to the mystique of the place. Inside, you will find a built-in fireplace in the living room, and baths with a whirlpool, so that you can enjoy the best of both classic and modern worlds. Enjoy both centuries’ best and have an out of this world experience here!
Top guest reviews
Amenities & Room:
for someone who is fine with the old home feel It does have many bedroomsI enjoyed the swing on the front porchThe first floor king and huge bathroom are magnificent but being right off the living room and kitchen is bit awkward with a large group Would still highly recommend thoughOur children and grandchildren enjoyed board games around the kitchen table-truly a memorable experienceThe house is definitely old with upgraded bathrooms and kitchenCleanliness:
The house was clean and nicely decoratedIt was clean and the property managers were very helpful in making sure our stay was comfortableHost:
My sisters and I had always talked about visiting Door CountyOur family finds the furnishings so nostalgic and unique--we always have conversations about certain items" The flowers trees lawn and lake make this setting gorgeousWe've stayed here multiple times -- this time we brought some friends and the house was so accommodating Great private space for each couple as well as good common space for staying in and having ...2 families with kids - a wonderful winter weekendRead more reviewsLocation:
Eight of us stayed at Orchard House for the Peninsula Century Spring Classic bike ridewe liked that it was a quieter settingbut we really loved "coming home" to the house and calmLocated in a great place in Bailey's Harbor -- right down the road from a pub Door County Brewing and dinner locationsIt's basically a 10 minute drive to most of the other little towns where we would shop and eat
The comfiest city in the US
If you’re still on the fence about whether to visit Bailey’s Harbor or not, here’s a fun fact to sway you: back in 2016, this destination was voted as the comfiest city in the US. To drive the point home; Bailey’s Harbor was, in 2018, rated as Wisconsin’s prettiest town. Experience these priceless features by staying in the comfiest city in the country.
History
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