Family-friendly vacation rentals in Sister Bay

4.91 out of 5 average rating, 101 reviews

A charming house stands amidst lush greenery, framed by a white trellis adorned with climbing plants and colorful flowers. The exterior features a steep roof and multiple windows, inviting natural light into the space. The walkway is bordered by vibrant foliage, enhancing the tranquil setting.

Cottage in Sister Bay

The Charm of Door County

A delightful retreat in perfect DC location. Ideal for a romantic weekend for a couple or perhaps for a family with two younger children. The retreat has two very large rooms, one featuring a sumptuous King bed, glass-topped table and four upholstered chairs, the other has a library/living-room feel - with several hundred books decoratively arranged. This has a Queen Sofabed, largeTV with Cable Netflix & Prime, and mini-fridge, microwave, coffee-maker & basic dinnerware. Pretty, private patio.

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, 121 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!

4.97 out of 5 average rating, 307 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.

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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, 102 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.

4.92 out of 5 average rating, 385 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

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.

4.99 out of 5 average rating, 120 reviews

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.

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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, 306 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

LocationHospitalityCleanlinessIndoor spacesComfortFamilyDecorHot tubAmenitiesKitchenOutdoor spacesNearbyPetsBathroomSleep qualityAccuracyGetting aroundBikingQuietLayoutParksWalkabilityCheck-inGrillConditionAccessBackyardValueHikingViewCheckoutWifiTVBeachAir conditioningParkingNoiseLaundryLong stayHeating

5.0 out of 5 average rating, 111 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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5.0 out of 5 average rating, 244 reviews

Cottage in Sister Bay

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

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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4.98 out of 5 average rating, 121 reviews

The modern lake house is framed by tall trees and features expansive floor-to-ceiling windows, providing views of the interior. Soft outdoor lighting subtly highlights the sleek architecture, while the lush green lawn invites a serene evening atmosphere.

Home in Clay Banks

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.

4.98 out of 5 average rating, 183 reviews

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.

Cottage in Sister Bay

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.

LocationCleanlinessComfortHospitalityDecorIndoor spacesQuietOutdoor spacesSleep qualityNearbyKitchenAccuracyAmenitiesFamilyGetting aroundConditionCheck-inViewGrillParksLaundryBathroomHikingCheckoutBikingTVParkingSolo travelLong stayBreakfastBackyardBeachNoiseValueEV chargingAir conditioning

4.95 out of 5 average rating, 138 reviews

A log cabin exterior is showcased, featuring a steeply pitched roof and a large porch area. Two seating chairs are positioned near the entrance, with seasonal pumpkins placed along the front. The surrounding trees display autumn foliage against a clear blue sky.

Cabin in Sister Bay

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

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Popular amenities for Sister Bay family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 111 reviews

Hot Tub | Sauna | Bar | Arcade | Fire Pit

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4.9 out of 5 average rating, 102 reviews

A spacious living room features a stone fireplace as a focal point, flanked by large windows allowing natural light. Two comfortable armchairs and a leather sofa are arranged for relaxation, with a coffee table in the center. A ceiling fan adds a touch of convenience.

Condo in Egg Harbor

Spacious Private Condo + Indoor Pool!

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4.93 out of 5 average rating, 240 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

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4.9 out of 5 average rating, 213 reviews

The living area features large windows, allowing natural light to filter in, illuminating the comfortable seating area. A wooden dining table is set with placemats, and a chandelier hangs above. A small balcony is visible through the sliding glass doors.

Condo in Egg Harbor

DoorCo Happy Place @Landmark Resort

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4.86 out of 5 average rating, 202 reviews

Northern Lights Farmhouse with Hot Tub

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4.88 out of 5 average rating, 115 reviews

Cozy Retreat | HotTub, FirePit, Arcade Fun & Dogs!

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4.97 out of 5 average rating, 149 reviews

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.

Cabin in Egg Harbor

Sunset Sanctuary- with outdoor hot tub

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4.89 out of 5 average rating, 123 reviews

A well-lit A-Frame cabin is viewed at night, with a bright blue hot tub in the foreground. The cabin features large windows and a door that lead to an outdoor seating area with multiple chairs. Soft lighting accentuates the cabin's exterior.

Tiny home in Stephenson

Natureside A-Frame Cabin: Cozy.Sauna.Hot Tub

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Family- and pet-friendly home rentals

4.95 out of 5 average rating, 176 reviews

Cabin in Sister Bay

Wismar Cabin Waterfront- Private Sand Beach

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.

4.91 out of 5 average rating, 126 reviews

Cozy Cottage in the woods

4.94 out of 5 average rating, 124 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

4.99 out of 5 average rating, 148 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

4.99 out of 5 average rating, 183 reviews

Home in Baileys Harbor

Winding Down - A Retreat on the "Quiet Side"

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.

4.88 out of 5 average rating, 126 reviews

Frontier Hideaway- Huge Game Room, Private 5 Acres

4.84 out of 5 average rating, 189 reviews

A serene lake view is captured at sunset, featuring hues of pink and purple reflecting on the calm water. A private dock is visible in the foreground, accompanied by a small ladder. Soft clouds drift across the sky, enhancing the tranquil atmosphere.

Loft in Ephraim

Eagle Harbor Cottage Loft

4.91 out of 5 average rating, 308 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

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 301 reviews

A view of the Evergreen Hill Condominiums showcases a row of two-level condos set against a backdrop of green trees. The image features a fenced swimming pool with a cover and lounge chairs arranged nearby, creating a serene outdoor space.

Condo in Fish Creek

Evergreen Hill A Whirlpool Condo by Pen State Park

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4.91 out of 5 average rating, 201 reviews

Townhouse in Egg Harbor

Newly remodeled Indoor pool/hottub Egg Harbor #51

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4.87 out of 5 average rating, 100 reviews

Three distinct buildings are arranged around a landscaped area featuring green grass and meticulously maintained flower beds. A bicycle is parked along the winding pathway, which is surrounded by young trees and stone features, contributing to a sense of openness and inviting atmosphere.

Cottage in Sturgeon Bay

Door County Waterfront Cottage (119)

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5.0 out of 5 average rating, 23 reviews

A view showcases a well-appointed home nestled among vibrant green trees, with hints of autumn colors. The surrounding landscape gently slopes toward a serene lake, reflecting the lush greenery and clouded sky.

Condo in Sister Bay

Peaceful Nature Retreat! Short Walk 2 Pebble Beach

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Place to stay in Sister Bay

A charming outdoor patio area is presented with a small dining table and black chairs, shaded by an umbrella. Planters with greenery adorn the space, which is surrounded by grass and trees, creating a serene environment for relaxation.

4.88 out of 5 average rating, 40 reviews

Cottage on SisterBay Inn grounds

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4.89 out of 5 average rating, 19 reviews

Home in Fish Creek

Spruce Suite | Downtown Fish Creek~Dog-friendly

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4.98 out of 5 average rating, 52 reviews

A hot tub is positioned on the patio, featuring jets that create a soothing water surface. Surrounding greenery adds natural beauty, while privacy is ensured by a barrier. Nearby, lounge chairs and vibrant pool toys are visible, enhancing the outdoor relaxation space.

Cabin in Sturgeon Bay

Waterfront/Pool/Hot Tub/Firepit/Game Room

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