Guesthouse holiday rentals in Door County

Three Sisters Meadow "Sweet" Retreat

Our two story guest dwelling is attached to the west end of the main house. We built it as a quaint guest haven to relax in*perfect for longer stays too* with an open floor plan room (21x21 ), fully equipped kitchen, dining area and living room. A southwest facing wrap around deck offers some shade and also a comfortable place to soak up the sun, watch a sunset. Adirondack chairs, picnic tables and a fire pit in the meadow. Hang your beach towels on the clothesline and make yourself at home .

Secluded Door County Getaway with a view

Fully finished, detached, living quarters located on the end of a secluded dead end road in Door County Wi. Perfect starting point for any Door county wi adventure or as a fisherman's base camp. Property within 2 miles of Lil Sturgeon Bay on Green bay. 5 beds. Kitchen includes Ninja air fryer, microwave , refrigerator, sink, coffee maker , pizza oven. WIFI, Youtube TV. Bathroom with shower. Fully Heated and air-conditioned. Room to turn and safely park your boat. Peak wildflower early aug

80-acre Rustic A-Frame

Escape to a fully renovated A-frame sanctuary on 80 private wooded acres with half a mile of Menominee River frontage. Rustic exposed beams, rich wood tones, and sleek updates. This guest house sits separately from the main home on the property, which will remain unoccupied if the A-frame is booked or the same party can book both properties—ensuring complete privacy and tranquility during your stay. Let the river’s gentle murmur and the forest’s quiet embrace lull you into peace—a hidden gem!

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.

Village Tree House, chill setting walkable to town

Brand new stylish upstairs studio apartment set among the trees with a beautiful wooded view yet centrally located. Enjoy the peaceful setting from the deck or hammock chairs. Walk into the waterfront village to coffee shops, beach, marina, restaurants, breweries, live music and more. Enjoy spinning some vinyl, pour over coffee, Turkish cotton towels and robes, puzzles, board games or anything else you dreamed of as a kid with the coolest treehouse hangout space around.

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!

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.

Spacious 2BR guest house with full kitchen

This stylish place to stay is perfect for a small family or group. Features two bedrooms with king beds, full kitchen and is in walking distance to Otumba Beach and downtown Sturgeon Bay. Otumba Park has a sand beach, playground, tennis courts, and a covered pavillion. Potowatomi State Park is a short bike ride away and we are a block off the Ice Age National Scenic Trail as it travels through Sturgeon Bay to its terminus in Potowatomi State Park.

Cozy 1 bedroom guesthouse with fireplace

Cozy one bedroom guest house within walking distance to downtown Sturgeon Bay and Otumba Park with sand beach, playground, tennis courts, and a covered pavillion. Potowatomi State Park is a short bike ride away and we are a block off the Ice Age National Scenic Trail as it travels through Sturgeon Bay to its terminus in Potowatomi State Park.

Jack's Little House

Keep it simple at this peaceful and centrally-located place. Located on a dead end road, short drive to Sister Bay, Ephraim and Bailey's Harbor. Free standing guest house on shared property with host and family. Please note this cottage is not a new build and is located in a country setting.

Stone Cottage - upper unit

Enjoy the beautiful upper of our stone cottage built in 1938. It features 2 bedrooms and 1 large bathroom with whirlpool tub, spacious living room with kitchenette. The location is ideal and within walking distance to downtown Egg Harbor.

Bay Shore Drive Guest House

Keep it simple in this peaceful and centrally-located Guest House. Just a few short minutes from Egg Harbor and Sturgeon Bay. Every thing you need for a relaxing getaway in the quaint home, nestled in the serene woods of Door County.