Holiday rentals in Sister Bay

Evergreen Hill B Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! All 3 B rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

Private 3BR Gem on 2.5 Wooded Acres- Close to All

Hinter Haven Cottage A place of solitude, beauty, and peacefulness—Hinter Haven Cottage is your perfect Door County getaway. This charming 3-bedroom, 2-bathroom retreat is tucked at the end of a private drive, surrounded by a quiet woods. You’ll feel worlds away, yet be just minutes from Door County’s most beloved villages and attractions. Thoughtfully maintained and protected with Mosquito Squad services for your comfort. Relax, recharge, and make lasting memories. Book your stay today!

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.

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

The Sister Bay Getaway: Water View & Downtown!

Updated 2 bedroom home - smoke & pet free. WiFi, Smart TV and A/C. Walking distance to downtown Sister Bay shops, restaurants, beach and more! This has been a favorite Door County location for many! We sincerely hope you enjoy our vacation home, Sister Bay, and everything Door County has to offer! Accept rental agreement (House Rules) prior to your stay. Airbnb bills and remits the WI State/County Taxes (5.5%); Door County Lodging tax (8%) & Sister Bay Resort tax (0.5%).

Cozy Cottage in the woods

New Renovations Jan 25: Windows, New Wall Unit AC, Updated Bathroom. Welcome to Hydrangea Haven. A cozy (1200 square ft) cottage tucked away on a quiet peaceful road, but close to all the fun. Nestled 3 miles north of sister bay, between Sister Bay and Ellison Bay. Bike down the low traffic beach road to all that downtown Sister Bay has to offer. Cozy up with the indoor fireplace, Adirondack chairs around the outdoor fire pit. NOTE: we are a 10 min DRIVE to beach not walk.

Sister Bay Eclectic Cottage

Stunning fresh + modern cottage ready for your visit NEW as of August 2018! Less than 1 mile walk or drive to Sister Bay Downtown + just minutes from the Beach! 3 Bedrooms: 1 king w/ on-suite bath, 1 queen w/ on-suite bath, twin trundle bed 3 full bathrooms: 1 on the main floor, 2 on-suite on 2nd floor Great cooks kitchen, fully stocked w/ open concept living space, w/ Sonos in kitchen! BBQ gas grille + awesome fire pit, expansive deck w/ dining space & lounge chairs

Mid Century Lake House with private beach

Come enjoy Door County in this beautiful lake house. Completely renovated with private beach access this is the perfect place to relax. Everything in this home is brand new! Conveniently located next to Ellison Bay & Sister Bay, enjoy all the hustle and bustle of Door County and retreat back to the serenity of the house Swim in the lake, paddle board, or take one of our bicycles and enjoy the scenery. Enjoy the winter snow shoeing, cross country skiing or snowmobiling.

The Key to Happiness

Sleeping 4-6 between 4 beds, Plum Retreat provides a one-of-a-kind Door County experience. With 2 large bedrooms (plus giant living room with queen sofa bed, dining area and full kitchen), the 1700 sq-feet have a charming cottage-like feel. Conveniently located with gorgeous perennial gardens, it makes a romantic, peaceful or fun space. Private lawn & patio/grill. Pretty much everything has been thought of. Last summer, all 37 groups of people gave it a 5-star rating!

101 | Luxury | Downtown Sister Bay | Door County

Owner operated + private entrance + no shared spaces Rare opportunity to rent the developer’s unit in Sister Bay’s newest, luxury, marina view condominium development! Custom cabinetry, quartz countertops, stainless steel appliances, garage parking, and more await you in this dedicated vacation rental. Walk out your patio door to 14 plus restaurants, bars, and coffee shops, including the famous Al Johnson’s. Virtual tour in highlights on IG "@101sisterbay"

Sister Bay A-Frame Cabin, Coffee Bar, Fireplace

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.

Lofted Pines Cottage

Settle in at Lofted Pines Cottage for your Door County stay! Located off the beaten path, but only a few minutes from downtown Sister Bay or Lake Michigan, Lofted Pines is elegantly situated among mature cedar and fir trees, yet open and airy. Whether you're relaxing on the wrap around porch, cozied up in front of the fireplace or enjoying the wood burning fire pit, Lofted Pines is the perfect spot to unwind after exploring the Door County Peninsula.