Family-friendly vacation rentals in Sister Bay

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.

Family-Friendly Farmhouse with Crib, Yard, Toys

Welcome to Oak & Orchard House, a family-friendly, renovated 1923 farmhouse on a quiet street in Sister Bay. Nestled between forest and field, and full of character and modern amenities, it sits alongside an old orchard of apple and pear trees, making it the quintessential Door County setting. Designed for easy travel with babies and young kids, the home includes a crib, high chair, toys, kids’ dishes, and a backyard playset, so you can pack lighter and enjoy a peaceful getaway.

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.

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

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"

The Glass House on Birch Bluff

The Glass House on Birch Bluff is named in honor of Fredrica “Fritzie” Glass who had it built in 1969. Fritzie was an artist, teacher and author who led a rich life both in Milwaukee and Door County. We’ve tried to honor her love of nature and beauty in this space. The cottage sits atop a private bluff on three gorgeous acres in Fish Creek. It is a wonderful place to be alone and unwind, and yet a short distance to all that Northern Door County has to offer!

2 Bed A-Frame in Sister Bay, Fire Pit, Coffee Bar

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.

Door County Lake House 50 min from Lambeau Field

We are excited to introduce our Architect-designed modern lake house in the town of Clay Banks! Enjoy serenity, sweeping views of Lake Michigan from a secluded back deck & expansive windows from every room in the house. Embrace slower living, waterfront amenities, neighborhood park with trails and the magic of lake life. You’ll enjoy water fun for the whole family, huge back deck with dining for 8, an outdoor lounge area, and fire pit near the water.

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.

3 Bed, 2 bath log cabin in Sister Bay w/ fire pit

Door County at its finest! Located minutes away from Sister Bay's main attractions. You can enjoy the privacy of the cabin a wooded lot with quick access to many activities in the surrounding area. 1 mile away from Northern Haus wedding venue 10 minutes drive from Peninsula State Park 20 minutes drive from Newport State Park 25 min from Whitefish Dunes State Park 20 min from ferry to Washington Island

Wismar Cabin Waterfront- Private Sand Beach

Step out your door onto a white sandy beach, listen to the waves, and feel completely tucked into nature—yet be just minutes from Sister Bay dining, shopping, and fun. Wismar Cabin at Sand Bay is one of the rare vacation homes in Door County that offers true waterfront privacy with sandy shoreline access, making it a guest favorite among Door County vacation rentals..