Family-friendly vacation rentals in Sister Bay

A serene lakeshore scene displays calm waters reflecting a clear blue sky. Gentle ripples move across the surface, while lush greenery frames the shoreline. A small boat is anchored nearby, offering a glimpse of leisure amidst the natural beauty. Rocky edges and smooth stones are present along the water's edge.

4.92 out of 5 average rating, 133 reviews

Sea Glass Cottage

Welcome to Sea Glass Cottage. Your Door County home away from home. This light and airy cottage is on the water with rock beach, beautiful sunrises, great room with beam ceilings & wood burning fireplace, kitchen ready for cooking and baking. A view of Lake Michigan from nearly every room. Perfect location for families or couples vacation. This cottage is tucked away on a wooded lot with an open backyard to enjoy sunshine and shoreline, or take a quick 5 minute drive to downtown Sister Bay.

A charming cottage features a distinctive turret, with a textured gray exterior and decorative trim. Soft lighting from the porch illuminates the entrance, creating a welcoming appearance. Lush greenery surrounds the home, highlighting a manicured lawn and pathways leading to the entry.

4.98 out of 5 average rating, 101 reviews

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!

Superhost

The charming home, surrounded by lush greenery, features a wide front porch and well-maintained landscaping. A serene backyard with outdoor seating invites relaxation, complemented by the peaceful natural setting that enhances the sense of seclusion.

4.87 out of 5 average rating, 139 reviews

Fall Into Fun• Hot Tub, Games,Dogs & Marina Stroll

Scandia by Getaway and Stay Enjoy the best of Sister Bay in this secluded retreat, just 5 minutes from the marina! The spacious backyard is perfect for kids and dogs, featuring a brand-new 5-seater hot tub, a cozy firepit, and a grill for starry nights. Inside, two sunlit living rooms offer plenty of space to unwind and make lasting memories. Whether you're seeking outdoor adventures or cozy nights in, this home is your perfect getaway. Book now and experience the charm of Door County!

4.96 out of 5 average rating, 241 reviews

The exterior of a cozy cottage is framed by lush green foliage. A white façade features a peaked roof and a small front porch with a large door. Sunlight filters through the leaves, creating a serene atmosphere in the surrounding garden.

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.

A private outdoor space is depicted featuring a pergola over a circular stone fire pit area. Surrounding greenery provides a natural backdrop, while patio seating is arranged nearby, inviting relaxation in a serene environment.

4.9 out of 5 average rating, 111 reviews

Maple Cottage, Cute & Cozy, steps to downtown.

Very cute and cozy home to enjoy Door County from. Large, private back yard with pergola and plenty of patio seating including a fire pit area. Charcoal grill on site. Home is centrally located between Washington Island and Egg Harbor. It's within .4 mile walking distance to downtown Sister Bay. Great place to get away and relax and still have the fun of the restaurants and shops nearby. This is our home away from home and we hope it will be yours too. (Maple Cottage RT-364)

A charming blue cottage with yellow shutters adorns the exterior. A well-maintained stone wall and vibrant flower beds enhance the entrance. The home features a single-car garage, a front porch, and large windows that invite natural light into the living space.

4.93 out of 5 average rating, 191 reviews

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%).

Superhost

The entrance features a bright red door set against a gray wooden wall. A small window with white trim is visible nearby. A snow shovel, a bucket, and two wooden sleds are arranged neatly next to the door, along with a cozy blanket and a pair of boots.

4.89 out of 5 average rating, 279 reviews

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

A spacious living area features a dining table with six upholstered chairs surrounded by warm, red walls. A cozy seating arrangement includes a pink armchair and a black rocking chair near a fireplace, with large windows allowing natural light to fill the space.

4.97 out of 5 average rating, 116 reviews

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!

5 out of 5 average rating, 104 reviews

An open-concept living space features a kitchen with a large island, stainless steel sink, and modern fixtures. A dining area with several rustic tables and mixed seating creates a welcoming atmosphere. Large windows showcase views of the marina, inviting natural light into the room.

Condo in Sister Bay

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 cottage showcases a distinctive A-frame design surrounded by lush greenery. A spacious wooden deck with yellow Adirondack chairs invites relaxation, while large front-facing windows allow for natural light and views of the serene wooded lot.

4.99 out of 5 average rating, 196 reviews

A-Frame - Coffee Bar, Gas 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.

A cozy cottage is nestled among tall trees, showcasing a white exterior with a stone chimney. The spacious porch features blue chairs, inviting relaxation. Lush green grass surrounds the home, complementing the peaceful rural setting.

4.99 out of 5 average rating, 140 reviews

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.

A cozy living room features a light grey couch adorned with navy blue pillows, paired with two beige armchairs. A round wooden coffee table is centered on a soft area rug, while large windows provide natural light and views of the surrounding greenery.