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.

4.93 out of 5 average rating, 161 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.

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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.

4.96 out of 5 average rating, 125 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!

LocationFamilyCheck-in

4.97 out of 5 average rating, 315 reviews

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.

LocationFamilyIndoor spaces

The charming exterior of the farmhouse features white siding and a welcoming porch with seating. Lush green trees surround the property, and a path of stone leads to the entrance. Large windows provide natural light to the interior spaces.

4.96 out of 5 average rating, 105 reviews

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.

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4.92 out of 5 average rating, 390 reviews

A spacious wooden deck overlooks the tranquil waters of Lake Michigan, featuring a round table surrounded by black metal chairs. Long benches line the edges, offering additional seating. Lush greenery can be seen along the shoreline, enhancing the serene atmosphere.

Home in Baileys Harbor

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

LocationFamilyKitchen

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.

4.94 out of 5 average rating, 211 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%).

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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, 312 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

LocationFamilyGetting around

4.99 out of 5 average rating, 125 reviews

A bright living space features modern furnishings arranged for comfort. Large glass doors provide a view of the lake and outdoor deck. Natural light fills the room, highlighting the soft area rug and contemporary chairs.

Home in Ellison Bay

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.

FamilyLocationGrill

5.0 out of 5 average rating, 114 reviews

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"

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4.97 out of 5 average rating, 360 reviews

Cottage in Fish Creek

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!

LocationValueHospitality

5.0 out of 5 average rating, 247 reviews

A-Frame Cottage, Fire Pit, Coffee Bar, 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.

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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.

4.98 out of 5 average rating, 188 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.

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Popular amenities for Sister Bay vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Sister Bay oceanfront vacation rentals

4.94 out of 5 average rating, 181 reviews

Cabin in Sister Bay

Wismar Cabin Waterfront- Private Sand Beach

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A charming lake house is seen from the water, surrounded by lush greenery. Two large trees frame the entrance, and the building features a pleasing mix of colors. A pebbled shoreline gives way to calm waters, reflecting the structure and the natural scenery.

4.97 out of 5 average rating, 192 reviews

Relaxing Waterfront Door County Lake House

LocationValueHiking

4.93 out of 5 average rating, 242 reviews

A cozy cottage is framed by surrounding trees, featuring a stone fire pit in front. Large glass doors illuminate the interior from within, while wooden siding adds a natural touch. Two outdoor chairs are positioned nearby, offering a serene view of the landscape.

Cottage in Sturgeon Bay

Peace of Beach, 4 season waterfront cottage

ValueFamilyIndoor spaces

4.93 out of 5 average rating, 103 reviews

A serene shoreline is lined with flat stone and gentle waves lapping at the water's edge. Sparse trees rise along the bank, casting slender shadows against the soft glow of twilight. The cottage is nestled above, blending harmoniously with the natural landscape.

Home in Washington

The Cottage of the Rising Sun

FamilyLocationLaundry

4.91 out of 5 average rating, 313 reviews

A fire pit area is set on a grassy lawn, surrounded by four blue Adirondack chairs. The pit is composed of stones and is positioned near the shoreline, with calm water and a picturesque view of the distant islands and clouds.

Cottage in Washington

Gull Cottage Waterfront Home on Washington Island

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4.97 out of 5 average rating, 104 reviews

A secluded outdoor area features a hot tub surrounded by wooden privacy walls. A fire pit sits nearby, with flames flickering and casting a warm glow. The backdrop showcases a scenic view of the beach and a colorful sunset sky.

Home in Menominee

Beachfront, HotTub, Incredible Views, BBQ, & Games

LocationValueHot tub

4.83 out of 5 average rating, 118 reviews

Two Adirondack chairs are placed facing a calm lake, with soft grass and sand underfoot. A fire pit sits between the chairs, surrounded by patches of wildflowers. An island is visible in the distance, enhancing the serene waterfront view.

Cottage in Washington

Hummingbird Cottage on Washington Island

FamilyValueIndoor spaces

Cottage in Washington Island

The serene water reflects the vibrant colors of a sunset, showcasing soft oranges and yellows blended with hints of blue. Gentle ripples create texture on the surface, enhancing the tranquil atmosphere of the waterfront setting.

Charming Waterfront Cottagem

ValueFamilyCheckout

4.84 out of 5 average rating, 111 reviews

Sister Bay cabin rentals

Superhost

The cabin's exterior is characterized by rustic wood siding complemented by vibrant red accents. A welcoming porch is visible at the front, with two rocking chairs inviting relaxation. Surrounding greenery enhances the outdoor space, creating a peaceful atmosphere.

Cabin in Ellison Bay

Historic Log Cabin by the Bay (Lake View)

FamilyLocationAccess

4.86 out of 5 average rating, 197 reviews

4.99 out of 5 average rating, 153 reviews

A cozy bedroom is framed by rustic log walls, featuring a spacious bed with a white comforter and a plaid throw. Two wooden bedside lamps provide soft lighting beside the bed, which is complemented by colorful pillows. Window treatments in plaid add a warm touch.

Cabin in Ellison Bay

Take Me Back Log Cabin

LocationFamilyCleanliness

The image captures a serene sunset over the bay, framed by tall trees. Silhouettes of branches contrast against the vibrant orange and yellow hues of the sun dipping below the horizon. A gentle grassy area leads toward a stone fire pit, enhancing the peaceful atmosphere.

4.97 out of 5 average rating, 152 reviews

Sunset Sanctuary- with outdoor hot tub

LocationFamilyBackyard

4.96 out of 5 average rating, 121 reviews

The exterior of a charming red cabin is framed by tall trees and lush greenery. A brick pathway leads to a covered porch, where a cozy seating area is available. Natural light filters through surrounding foliage, creating a peaceful and inviting atmosphere.

Cabin in Sturgeon Bay

Make Memories at our Cabin in the Woods.

LocationValueNearby

4.78 out of 5 average rating, 331 reviews

Cabin in Baileys Harbor

Door County Dreaming Cabin, Pet Friendly

FamilyLocationLong stay

4.98 out of 5 average rating, 183 reviews

The Cabin at Shady Grove

ValueFamilyView

4.97 out of 5 average rating, 177 reviews

A cozy living area is showcased, featuring a large sectional sofa with decorative pillows and a rustic wooden coffee table. A stone fireplace stands as a focal point, while warm lighting highlights the natural wood accents and a patterned area rug on the hardwood floor.

Cabin in Sturgeon Bay

Serene, cozy cottage in the woods

ValueLocationNearby

The lodge's exterior is characterized by a classic log cabin style, featuring large windows that allow ample natural light. Surrounding greenery includes well-kept shrubs and trees, with a vibrant red maple adding a burst of color against the serene backdrop.

4.93 out of 5 average rating, 176 reviews

Green Apple Lodge (loghome, hot tub & fiber wifi!)

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Pet-friendly vacation rentals in Sister Bay

4.99 out of 5 average rating, 184 reviews

Home in Baileys Harbor

Winding Down - A Retreat on the "Quiet Side"

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A charming cottage features a two-story design with a covered porch. Lush green landscaping, including hydrangea bushes, surrounds the entrance. The exterior showcases a mix of light-colored siding and a dark shingled roof, set against a backdrop of trees.

4.92 out of 5 average rating, 134 reviews

Cozy Cottage in the woods

LocationValueWifi

4.84 out of 5 average rating, 191 reviews

The exterior of the reconditioned barn is visible, featuring a blue wooden façade and large casement windows. A gravel driveway leads up to the entrance, surrounded by landscaped gardens with various plants and flowers, creating a serene and inviting setting.

Barn in Sister Bay

Three Sister's Cottage Barn Retreat

FamilyLocationHiking

4.93 out of 5 average rating, 130 reviews

The living area features warm wooden beams and a stone fireplace, creating a cozy atmosphere. Large windows provide natural light and a view of the outdoors. Comfortable seating is arranged with a sectional couch, two chairs, and a coffee table, inviting relaxation.

Cottage in Ellison Bay

Pet-Friendly, Cozy Cottage in Northern Door County

ValueFamilyComfort

Superhost

A spacious living area features a cozy fireplace surrounded by comfortable seating. Large windows allow natural light to illuminate the space, while a dining area and kitchen are visible in the background, providing an open and inviting atmosphere.

Home in Ellison Bay

Frontier Hideaway- Huge Game Room, Private 5 Acres

LocationFamilyWifi

4.88 out of 5 average rating, 126 reviews

4.97 out of 5 average rating, 140 reviews

A spacious living room is featured, designed with a comfortable sectional sofa and accent chairs around a circular coffee table. Natural light floods through large windows, complemented by a stylish fireplace and wall-mounted artwork showcasing sunset views.

Apartment in Egg Harbor

The Loft – Pet-Friendly Egg Harbor Rental

FamilyLocationCleanliness

Superhost

A bright living area features wooden beams and a cozy seating arrangement. A plush sectional and two upholstered chairs are centered around a coffee table, while a large artwork and a wall clock add character to the space. Natural light fills the room through two windows.

Home in Baileys Harbor

1900s renovated Farmhouse with spacious yard

LocationFamilyPets

4.85 out of 5 average rating, 149 reviews