66 properties available

Located in Baileys Harbor, Wisconsin, United States. Cute cottage in the center of the Door Peninsula - Pet Friendly! There's a full kitchen and a grill out side. Fire pit for roasting marshmallows, right next door to a winery, and walking distance to three restaurants. A perfect place to start no matter which way you want to go.

Located in Baileys Harbor, Wisconsin, United States. Baileys Harbor Waterfront Vacation Rental w/ Grill Experience the beauty of Lake Michigan at this charming 2-bedroom, 1-bath cottage in Baileys Harbor, WI! Perfect for couples or small groups, this vacation rental is situated along the shores of North Bay with breathtaking views from every corner. When you’re not busy on a water adventure, prepare some steaks on the charcoal grill or roast s’mores over the outdoor fire pit. If you’re looking to step out, explore miles of trails at the Ridges Sanctuary or visit the iconic Cana Island Lighthouse.-- THE PROPERTY --Door County Tourism Zone Lodging Permit:32-56-2804-00 | Fire Pit | Water Views | Quiet SettingBedroom 1: King Bed | Bedroom 2: Queen BedOUTDOOR LIVING: Charcoal grill (charcoal not provided), Adirondack seating, cornholeINDOOR LIVING: Smart TV, 4-person dining tableKITCHEN: Cooking basics, refrigerator, microwave, stove/oven, dishwasher, dishware & flatware, Keurig coffee maker, ice maker, toaster, Crockpot, water filterGENERAL:

Located in Baileys Harbor, Wisconsin, United States. Charming Cottage Charming, Clean, Quiet and Secluded . Nestled amongst the Cedars and within a very short distance to Moonlight Bay and Cana Island Lighthouse! This newly Remodeled , freshly Painted , Cozy, Charming Cottage is sure to be your Perfect Couples Getaway!1 bedroom 1 bath with additional pullout twin sofa, kitchen, Queen Bed, Full laundry , Walk in shower . Perfect for a peace and Quiet Door County Experience . Within walking distance of Moonlight Bay to launch your kayak, Canoe, Go Fishing or just to sit and relax . Mud Lake Wildlife area is Across the Street with Hundreds of Acres of Wildlife Sanctuary. Minutes from Baileys Harbor restaurants , beaches , shopping, The ridges Sanctuary and Cana Island Lighthouse . A true Door County Experience !

Located in Baileys Harbor, Wisconsin, United States. Rustic Log Home located near Baileys Harbor Welcome to our authentic New England log home, built by our family in 1976. This charming home has many recent updates, including hard wood flooring, fully remodeled bathrooms, and an updated kitchen. Lounge on one of the two covered porches, perfect for enjoying a morning cup of coffee or evening glass of wine. Enjoy cooking outdoors in the picnic area. Relax in the spacious living room with a cathedral ceiling and stone fireplace. We are located 3 miles south of Baileys Harbor on a private 3 acre lot surrounded by woods. Enjoy a leisurely walk down the road to explore the lakeshore or watch the sunrise. Sit on the porch and watch the mystic hummingbirds as they enjoy their nectar. An abundance of wildlife can be viewed. In the backyard is a picnic area with a grill and picnic table for outdoor meals. In the evening you can stargaze by the fire pit in the backyard. It’s is only a short drive to Maxwelton Braes Golfcourse or the charmi

Located in Baileys Harbor, Wisconsin, United States. Cozy Baileys Harbor Cottage on Lake Michigan! Experience the lakeside charm of Wisconsin from the comfort of this 3-bedroom, 1-bathroom Baileys Harbor vacation rental. ‘Wildwood’ offers a well-equipped kitchen, Smart TVs, and a covered porch with beach views, this cottage is perfect for sharing memory-filled moments with ease. Take time to explore quiet nature trails, spend an afternoon at local golf courses, or experience the fishing and boating fun that flows out from Lake Michigan. There’s something for everyone to see and do!-- THE PROPERTY --Door County Tourism Zone Lodging Permit #02-56-1640-21 | Covered Porch w/ Adirondack Chairs | Lake Access, Boating & Marina Nearby | 1,700 Sq FtWhether you need a summertime getaway with family or you’re searching for a cozy retreat with friends, waterfront 'Wildwood' promises an unforgettable vacation!Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Living Room: Sleeper SofaINDOOR LIVING: Smart TVs, DVD player, fireplace,

Located in Baileys Harbor, Wisconsin, United States. Beautiful Lakeside Cabin - Great Location & Amenities (Canoe, Kayak, Boat, etc) Come enjoy our 1,500 sq. ft. lake house on Kangaroo Lake. This home maintains its original 1940's cottage charm with the classic Door County stone fireplace(non functioning), cedar walls, and wood floors. The house comfortably accommodates 8-12 guests with 4 bedrooms and 2.5 bathrooms. The dining room has a lakeside view and seating for 12. There is plenty of space for outdoor dining, lawn games, and relaxing. *Satellite TV and WiFi provided*.The first floor master bedroom has a queen size bed, its own private bathroom and a patio facing the lake. The upstairs has 3 bedrooms and another full bathroom. The first bedroom has 2 twin beds, the second bedroom has a full bed, and the large third bedroom which faces the lake has a queen size bed and full futon. There is also a queen size sofa bed in the living room and a half bathroom on the first floor. The fireplace is beautiful but not functioning.Kang

Located in Baileys Harbor, Wisconsin, United States. Door County-Cozy Cabin nestled in The Woods, and Close to all DC has to offer! Welcome to Porcupine Cabin! This clean and cozy log cabin is nestled among mature hardwoods and evergreens on 1.5 acres in Baileys Harbor, a short distance into downtown. The first floor has an open concept living room with a gas fireplace, kitchen, dining room, and full bath. Upstairs are 2 large bedrooms and a full bath. Sit and relax on the large screened-in porch, covered front porch, or by the outdoor fire pit and enjoy privacy and nature all around you. Located within minutes of Sister Bay, Fish Creek, Ephraim, and Egg Harbor, this is your ideal vacation home to explore all that Door County has to offer! *Peak season rental is Sunday-Sunday (7 nights). Off-Season 2 Day Minimum Rentals ** Porcupine Cabin is professionally cleaned and provides commercially laundered linens.*** Outdoor cameras in place for property safety and security

Located in Baileys Harbor, Wisconsin, United States. Chicory Lake House- Kangaroo Lake Gem with Kayaks, Fireplace and Game Room Welcome to Chicory Lake House - a premier family escape in the heart of Door County!Our newly remodeled Kangaroo lakefront vacation home is located on a private road, just adjacent to the historic Kangaroo Lake causeway. Surrounded by calming waters and gorgeous lake views, Chicory Lake House is the perfect Door County retreat. Watch the Mergansers swim directly off the lakeside deck and patio, fish from the pier, or explore the lake on the provided kayaks and paddle boards. Wake up to direct views of the lake and spend evenings cozying up to a roaring lakeside bonfire. With all three bedrooms on one level, a gas fireplace, a large yard for outdoor games, and a game room complete with bumper pool and shuffleboard, Chicory Lake House is the perfect place to make memories for all ages and seasons.Nestled among the reeds and mature trees on Kangaroo Lake's shoreline, Chicory Lake House feels like a true escape, ye

Located in Baileys Harbor, Wisconsin, United States. Rockledge Cottage, Cozy Private Cottage situated on a Rock Bluff overlooking Lake Michigan Cozy Private Cottage Situated on a Rock BluffBaileys on the Rocks "Rockledge" Cottage is a private cottage located on a small rock bluff in Baileys Harbor, Wisconsin in beautiful Door County. Situated on a wooded lot and directly across the street from Lake Michigan, you'll find it hard to believe you are in the village of Baileys Harbor and within walking distance of its popular beaches, harbor, restaurants and quaint shops.The cottage was built in 1939 and is 1 story (684 sq ft), with the bathroom and both bedrooms are on the main level. 1 bedroom features a queen sized bed while the other bedroom has a set of twin beds. There is also a sleeper sofa in the living room. The bathroom features a tub/shower combo. This charming cottage sits atop the limestone bluff with partial water views and a quaint screened porch.Guests have full access to the cottage. The cottage is on a shared lot with anothe

Located in Baileys Harbor, Wisconsin, United States. Three Bedroom Lake House with Boat Dock Situated on the eastern shore of pristine Kangaroo Lake is your 3 bedroom relaxing vacation retreat. Reminiscent of childhood memories, swim all day, fish off the dock at sunset. Investigate the lake shore with your watercraft, or just sit by the lake side fire pit and marvel at the summer sky. Catch one of the many outstanding performances Door County has to offer. Come join us, you’ll never want to leave.*Turnover day is Saturday during the peak season*** No Camper or Boat parking at any time. Contact the local township for information on public overnight parking **AccommodationsShared Boat Dock (boats on dock are privately owned and not for use of renters)Canoe and Paddle Boat for use of rentersBoatingCribsDeckDishwasherSatellite/DVD PlayerFire PitFishingFull KitchenGrillKitchen FacilitiesMicrowavePets With ApprovalShared WaterfrontAC unit in living room and Queen bedroom

Located in Baileys Harbor, Wisconsin, United States. Secluded home on Lake Michigan. Perfect for families and groups. Pet friendly. Recently renovated, Thimbleberry Castle House provides an unique space for family and group gatherings. Situated within an easy walk to great trails , this secluded location offers walks along the Lake Michigan beach and on wooded paths. Pets ok.

Located in Baileys Harbor, Wisconsin, United States. Private, Updated Baileys Harbor Home: The Roost Welcome to The Roost, hosted by Simple Life Rentals! Updated in 2023, this 3 bedroom, 2 bathroom, 1-story home showcases beauty in all the details. The home is situated on a private road, nestled on a 2.25 acre wooded lot with a large pull through driveway perfect if you are towing a boat. Enjoy the peace and serenity of the woods with the convenience of a short walk or drive to downtown Baileys Harbor and Lake Michigan. Visit shops, restaurants, the harbor, The Ridges Sanctuary, and more!We love our family pet dogs and welcome yours too. Your well behaved dogs are allowed with prior approval. This property allows up to 2 dogs. There is a fee of $50 per dog/per night, which is collected separately and approximately one week prior to your check-in date.*This is a quiet community with residential neighbors. This home is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate bachelor or bachelorette p

Located in Baileys Harbor, Wisconsin, United States. Sunrises and S'mores!- Miles of Sand Beach -Prime Time 2025 Going Fast! A Shoreline Retreat Awaits! NOTE: *We welcome conscientious, Non Smoking, Adult Guests Only at A Shoreline Retreat.*This home requires a seven (7) nite minimum June, July, and August-Friday to Friday*Other Spring and Fall Dates - 4 NITE MINIMUM IS REQUIRED Thank You!******ASK US ABOUT EXTENDED STAYS - (30 days or more is tax free!)******* PROPERTY HIGHLIGHTS*This is a casual and comfortable 3 bedroom/2 full bath home with an appealing mix of rustic and modern that sleeps 6 - directly on Lake Michigan. *A Shoreline Retreat offers stunning, open lake views via expansive windows, and the perfect location 15 minutes north of Sturgeon Bay and one mile north of downtown Jacksonport. *Enjoy spectacular sunrises, swimming in Lake Michigan, s'mores around the firepit, a walkable beach both north and south, and a spacious yard for sunning and relaxing. *Enjoy swimming, kayaks, paddle boards (available to rent right in

Located in Baileys Harbor, Wisconsin, United States. Welcome to your cozy home away from home Kookaburra Cottage at Kangaroo Lake! Kookaburra Cottage at Kangaroo Lake is a brand new, gut rehab of an artist’s cottage with all the amenities you could ever need. Tucked away on a beautiful and quiet 2-acre wooded lot, the cabin offers the private getaway you are looking for while being centrally located to all of Door County’s treasured public spaces. Access to Kangaroo Lake’s beautiful, calm waters for swimming and kayaking is just a short walk south, and cold beer and warm food awaits you just a quick walk north to Coyote Roadhouse. Baileys Harbor is just a 10 minute drive away, and all the wonderful restaurants and shops of Door County are close-by.Kookaburra Cottage sleeps four comfortably with two-bedrooms and one bathroom and is perfect for a small family or a couple’s getaway. The beautifully appointed cottage has a warm living space with a large HD Smart TV, Bluray player (and so many movies!), an air-conditioner, and gas fireplace.

Located in Baileys Harbor, Wisconsin, United States. Bailey's Harbor Cabin Secluded in Woods,Walking distance to Kangaroo Lake-DUPLEX This property is walking distance to Kangaroo Lake. Featured on Travel Wisconsin! NEW AC installed in April of 2019! I have two kayaks for rental as well. This is an A frame cabin with a loft area that has 3 beds. There is an additional bed downstairs. The backyard has patio and is completely secluded by trees that surround it. It is a short drive (roughly 10 minutes) to the shops, restaurants, ice cream/candy stores, and the Lake Michigan Harbor. There is so much around to do, kayak, snowmobile, ice fish, regular fishing, hiking, biking and so much more! It is available all year round with a cozy wood burner. The snowmobile trails run right through with plenty of parking on the lot. Across the street is a great restaurant/bar that hosts events and has delicious, reasonably priced food. This place is great for families, friends, or a couples getaway. Early check in is ONLY available if the clean

Located in Baileys Harbor, Wisconsin, United States. Newly renovated with over 250 feet of Shoreline! Location: Baileys Harbor, North BayBedrooms: 3, Queen plus Twin Trundle, King, FullBathrooms: 2, Full with shower/tub, Full with showerMax Occupancy: 6No SmokingPets: YesSatellite/Cable: YesInternet: Wi-FiAir Conditioning: Yes, First FloorFire Pit: Yes, near waterThis charming vacation rental in Bailey’s Harbor has been enjoyed by our family for over 40 years and is now being offered to your family. The house was recently renovated with modern amenities, such as a Viking stove, while still keeping its rustic touch with its old rock fireplace from the 1800’s.This property is located on the corner lot of North Bay with over 250 feet of shoreline. Watch gorgeous sunrises on the dock or deck in the morning or sit under the stars near the fire pit at night. House contains 3 bedrooms and 2 bathrooms and even a 2 story playhouse. Our property is close enough to Gordon’s Lodge to kayak over for a quick snack or cherry margarita at Top Deck. It

Located in Baileys Harbor, Wisconsin, United States. Baileys Harbor Yellow House with a view Situated in the heart of down town Baileys Harbor, Wisconsin. You can sit in the kitchen and see Lake Michigan as you drink your morning coffee. No need to drive if you do not want to, you have restaurants, bars and shops all within walking distance. You have the whole house to yourself, but we own a coffee shop one building over, in case you need anything. The house is a late 1920 s house, but newly upgraded, with a new kitchen and bathroom.

Located in Baileys Harbor, Wisconsin, United States. Baileys Harbor retreat across from Lake Michigan - WALK / BIKE to town! We welcome you to come enjoy this cozy vacation home in Baileys Harbor! Our property is located across the street from Lake Michigan and within walking / biking distance to town where you can enjoy parks, restaurants and shops and find beach access. Enjoy your morning coffee on one of the two balconies while you listen to the waves of Lake Michigan. Enjoy access to free WI-FI. Grill out or gather around the table for a family meal while all being together in the open concept floor plan. This custom built home is approximately 20 years old and is very well kept and perfect for your family to enjoy! The main floor incorporates the kitchen, dining and family room in an open concept that will bring all the guests together for meals, games etc.. Large windows with sliding glass doors allow access to a large balcony with a table for seating: a perfect spot to start your day or wind down the evening.Featuring 3 be

Located in Baileys Harbor, Wisconsin, United States. Private Kangaroo Lake Waterfront Estate - Baileys Harbor Welcome to Kangaroo East Shore, hosted by Simple Life Rentals! Relax and play at this private, waterfront home on the east shore of Kangaroo Lake in Baileys Harbor. This stunning 4400 sq ft lodge is sure to impress boasting a combination of rustic and modern with an expansive estate like feel. Not only does the home sleep 14 people, it can also accommodate everyone at the large reclaimed barn wood dining table. It includes 6 separate sleeping spaces, 5 bathrooms and plenty of space for guests to enjoy!The sandy waterfront includes a new, long dock and is a perfect place for all guests, including children to enjoy swimming, fishing or using the kayaks provided. Enjoy gorgeous sunsets, as the property faces west and then soak in the beauty sitting around the firepit near the water in the evening. Enjoy the cozy evenings together with a wood burning fireplace or the fun summer days on Kangaroo Lake.***This property is located in a q

Located in Baileys Harbor, Wisconsin, United States. Century Old Door County in-Town Farmhouse The Orchard House is located in the shore side village of Baileys Harbor, Wisconsin. It is a two-story house with a total of 4 bedrooms and 3 baths to accommodate up to eight guests! A fully restored century old in-town farmhouse stands sentinel over old apple orchard and gardens. The first floor offers a king size bedroom, fully equipped kitchen, living room with fireplace, and bath with fireplace & double whirlpool. The second floor features 3 bedrooms and 2 baths. Enjoy a fun-filled family getaway with all the amenities; original wood floors, pocket doors, high ceilings, central air, wireless, satellite TV, DVD/CD, washer/dryer, gas grill, croquet, linens, towels. Stroll to shops & restaurants, relax on the wide front porch, complete with porch swing. Centrally located to all of Door County. 4 night minimum Memorial Day weekend through October, 2 night minimum during our quiet season, smoke-free, pet free. Call 1-920-8399222 to place a re

Located in Baileys Harbor, Wisconsin, United States. Quintessential Door County cottage just steps from the water! We are following these procedures in the link below to clean for your stay at our properties. Please feel free to click on the link to read about what we are doing to make your stay as safe and comfortable as possible. We look forward to seeing you all soon. https://www.vrbo.com/discoveryhub/tips-and-resources/improve-performance/covid-19-cleaning-tips Quintessential Door County cottage has the character, style, and location you have been looking for. Relish the charm of this one story cottage with three bedrooms and two baths. Open flow from living room, kitchen to great room makes the cottage live large. Want to be outside without bugs? No problem – relax on the 40 foot screened porch and enjoy that book you have been meaning to read. Two wood burning fireplaces create a warm and cozy environment during the Door County ever changing seasons. Prepare meals in the well-stocked kitchen and eat on the front porch, the ba

Located in Baileys Harbor, Wisconsin, United States. West Meadow Rental! Welcome to our home in Door County! This house & guest house is a great place to vacation & also work remotely with STARLINK satellite internet! Both the main house and the guest house are included in the rental price so there is ample space and amenities for all guests. This home is in a great location! The property is 10-15 minutes from 4 beaches, wonderful restaurants, 2 boat launches, hiking and biking trails in Peninsula State park, golf courses, and boat and jet ski rentals.The spaceThere are two newly remodeled homes on our 10 acre property with mowed walking paths and ample space for kids to run.; a main house featuring 2 bedrooms & 2 bathrooms, a chef’s kitchen complete with Blue Star range and beautiful guest house with 2 queen beds, a spa bathroom, sauna, and rain shower. There is a wrap around deck and grill outside for entertaining and outdoor summer dinners. There is also a beautiful basswood sauna and rain shower in the guest house for everyone to e

Located in Baileys Harbor, Wisconsin, United States. Tranquility and Serenity/Family Retreat. Kangaroo lake is a 1100 acre lake in the middle of Door County, Wisconsin, Our Lake house faces the south west which allows the beautiful sunshine to pour into the property and incredible sunsets. The home is less than 50' from the water *Large patio facing the lake* Swimming out the front door*Kayaks, Canoe and paddle boat supplied* 10 beds* 4 full size bathrooms* Outside fire pit with fire wood supplied.* 4 bikes on the property for you to enjoy.* 5 minutes to Egg Harbor, Fish Creek and Baileys Harbor* 9 Minutes to Peninsula state park* Door County has over 298 miles of pristine shore line* Hiking and biking trails Beaches galore*Wilson's Ice cream*Boating and many beaches*Norther sky Theater* Cleaning and Disinfecting per (CDC) guidelinesThis is what one our our guest loved: We spent five days in this house. It turned out to be better than its photos. The house is right on the banks of the Kangaroo lake. I had my coffee on the pier everyday

Located in Baileys Harbor, Wisconsin, United States. Stunning Studio just steps from the Bjorklunden Trail System in Baileys Harbor Welcome to Muirfield Flat, hosted by Simple Life Rentals! This stunning new construction studio apartment is nestled on a nicely wooded lot next to Maxwelton Braes golf course and the Bjorklunden trail system which has stunning views of Lake Michigan. This quaint upstairs studio apartment includes a king size bed and a pull out couch. The unit will comfortably sleep 3 adults, or 2 adults and 2 children, with room for a pack and play for a larger family. There is a kitchenette with a microwave, mini refrigerator, and coffee maker. There is also a full bathroom, a dining area, wifi, and Roku TV.This unit has a separate entrance from the main house. The main home may be available for rent, please send an inquiry for availability and pricing.***This property is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate partie