Holiday houses in Kangaroo Lake

Cottage in Baileys Harbor

4.96 out of 5 average rating, 24 reviews

Fabulous 2 Bed, 2 Bath Cottage On Kangaroo Lake

Carraigeen Cottage is a new 2 bedroom, 2 bathroom cottage right on the shores of beautiful Kangaroo Lake. It has a fully equipped modern kitchen with granite countertops, new stainless steel appliances, including a full sized dishwasher, full stove, large refrigerator, and new washer / dryer. It has 4 queen pillow top beds perfect for 1-2 families or a group of friends. Outside there is a BBQ and picnic style tables. There are several chairs. We have a spot for a boat at the dock. You are welcom

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.

4.94 out of 5 average rating, 65 reviews

Home in Baileys Harbor

Charming Cottage set on 5 Country Acres

Charming rustic cabin with elegant interior on 5 private acres in an overgrown apple orchard. We are a short walk down the road to Door County’s best swim spot! Four beds and 1.5 baths. You are surrounded by nature yet centrally located to all Door County has to offer. We have a fully stocked kitchen, wood burning fireplace, screened back porch, charcoal grill, and fire pit area along with mowed paths in the orchard. King in master, Queen in second bedroom and two Twin Beds in the Open Loft.

4.91 out of 5 average rating, 120 reviews

Cabin in Ellison Bay

Unique architect-designed home on waterfront bluff

An architect gem with a million dollar view. Located on the bay on a private drive near Ellison Bay, it’s close enough to town but far enough away to be secluded. The main house features a roomy living area with sleeper, kitchen, dining room, shower bath, and loft bedroom. The newly-finished "Garage-Mahal" features a full bathroom, two bedrooms (one full and two twins), kitchenette, and small living room with sleeper. This separate building is ideal for anyone who likes their own space.

4.97 out of 5 average rating, 226 reviews

Guesthouse in Fish Creek

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.

4.92 out of 5 average rating, 184 reviews

Cottage in Sturgeon Bay

Peace of Beach, 4 season waterfront cottage

Beautiful 4 season, private 2 bedroom Knotty Pine Cottage located on the shores of Lake Michigan just 10 yards away from water in Sturgeon Bay, WI. 2 BR/1 bath cottage with beautiful stone, wood burning fireplace. A fully equipped kitchen with high bar dining which seats 8. Lots of living space with leather sectional and full size hide-away sofa sleeps 2, Main Guest Room 1 w/ queen log bed and Guest Room 2 with full size log bunk beds, Large screen tv, wifi and panoramic lake view.

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.

4.79 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.

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.

4.97 out of 5 average rating, 358 reviews

Apartment in Egg Harbor

Award Winning Modern Flat in Egg Harbor - #104

The Flats on Church Street are Door County's newest, most modern vacation rentals. The days of kitsch and lace are over! We built these rentals to give visitors to Door County something different. Each 1-bedroom/1-bathroom apartment features floor-to-ceiling windows, heated floors, a small kitchen, a king sized bed and a queen-sized sleeper sofa. They're centrally located within walking distance of all that Egg Harbor has to offer.

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.

4.97 out of 5 average rating, 150 reviews

Cabin in Egg Harbor

The Cabin at Shady Grove

Set among five acres of mature and private woods, this newly renovated vintage log home has 2 bedrooms, 2.5 baths, and sleeps five guests. The property is completely secluded and private, yet only a five minute drive to town and the beach. Relax and unplug. Reconnect with your family, friends, and nature. Welcome to the cabin at Shady Grove.

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Other great holiday rentals in Kangaroo Lake

Home in Baileys Harbor

4.7 out of 5 average rating, 20 reviews

Whit's Acre

MaryRating, 5 stars7 months ago

Great Door County experience. Spacious and comfortable residence. Showers and sleeping were excellent. Internet a little spotty and I recommend bringing a streaming device since none are provided. Shout out nearby Coyote Roadhouse and Waseda Farms are definitely worth stopping at. Wonderful time.

4.98 out of 5 average rating, 66 reviews

Home in Baileys Harbor

Tucked Away Ranch in the Woods ~ Mins to Harbor

JulianaRating, 5 stars2 days ago

My family and I stayed at this gorgeous house for 3 days to explore Door County. Check in was a breeze, and Jasmeet and his team were quick to answer any questions we had. Once we arrived, we loved the space so much that we decided to extend our stay by 1 night and again, it was a quick and easy process. Thank you for creating and sharing such a lovely space!

5 out of 5 average rating, 8 reviews

Home in Fish Creek

Alma at Loma Cottages

DiannaRating, 5 stars1 month ago

Our stay at the Alma cottage was even better than we expected! The minimal yet thoughtful design boasted large windows that really let the surrounding landscape in allowing for a peaceful ambiance throughout the cabin. The beds were comfortable and we felt at home. Everything was wonderful. We will be back!

5 out of 5 average rating, 7 reviews

Home in Egg Harbor

Lavender Farms, 2024 New Construction, Egg Harbor

NicoleRating, 5 stars3 days ago

This is an incredible home! Everything is beautiful, pristine, and every amenity you can think of was available to make our stay feel like we were at home. It was perfect for our family of five!

4.95 out of 5 average rating, 77 reviews

Condo in Sister Bay

2 bed 2 bath Condo

HannahRating, 5 stars2 weeks ago

Jared’s apartment was in a perfect location on the peninsula. It’s fairly centralized to all of the activities that my family and I wanted to do (20-30 minute drives to popular attractions in door county; state parks, beaches, kayaking, shops, ice cream parlors, etc.). It was perfect walking distance to attractions in downtown Sister Bay (~5-10 walk max). The apartment is on top of a hill so depending on your food coma after dinner, it may feel like a hike. The house was very clean, nicely decorated. All of the essential amenities were available for use and some extras as a plus! Jared was easy to communicate with and gave clear instructions and house rules. Nice neighborhood and well lit. No safety concerns especially with traveling with a toddler. We would love to come back again and stay in this listing.

Cabin in Baileys Harbor

4.67 out of 5 average rating, 6 reviews

Chalet Cabin: Sunset Shores - Kangaroo Lakefront

AliahRating, 5 stars8 months ago

Our October 2024 trip to Door County was made easy with Simple Life Rentals. We initially received the wrong code but received the accurate code within a few minutes of contacting Simple Life via Airbnb. Only complaint would be that the WiFi didn’t work - we didn’t need it, but if we had planned to study or work remotely we would not have been able to the entire weekend. Overall, great stay!

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!