Family-friendly holiday 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, 159 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.

FamilyIndoor spacesPets

4.97 out of 5 average rating, 313 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.

Indoor spacesFamilyCondition

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, 104 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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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, 210 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%).

Indoor spacesKitchenNearby

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, 311 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

KitchenFamilyLaundry

4.99 out of 5 average rating, 124 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.

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 113 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"

KitchenFamilyPets

4.97 out of 5 average rating, 359 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!

Indoor spacesFamilyBarbecue

5.0 out of 5 average rating, 247 reviews

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.

FamilyIndoor spacesWi-Fi

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, 187 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.

FamilyKitchenTV

4.95 out of 5 average rating, 140 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

KitchenIndoor spacesPets

4.98 out of 5 average rating, 184 reviews

The entrance of Blue Moon Cabin features a blue front door with decorative glass panels. A welcome mat is laid on the wooden porch, which is complemented by a rustic wooden wall. A potted plant and a blue chair are positioned beside the door.

Cabin in Sister Bay

Blue Moon Cabin

Looking for serene and peaceful? Snuggle in at Blue Moon Cabin during your Door County visit! Nestled in a small grove of trees on our 20 acre farm, you'll find yourself away from it all, yet only a short drive from town. No pets. No smoking. If you're searching for a place to accommodate up to 6 guests, please see our listing - Blue Moon Cabin +2.

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Popular amenities for Sister Bay family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Luxe

A spacious living area is illuminated by natural light, featuring a large stone fireplace at its center. Comfortably arranged sofas are complemented by patterned cushions, while a wooden coffee table holds various magazines. Floor-to-ceiling windows provide views of the surrounding greenery.

Home in Clay Banks

4.98 out of 5 average rating, 128 reviews

Door County Lake House

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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.

4.9 out of 5 average rating, 105 reviews

Spacious Private Condo + Indoor Pool!

KitchenFamilyComfort

The entrance to Meadow Ridge is marked by a stone facade featuring two blue signs. Surrounding greenery is complemented by pumpkins arranged on a stone outcrop, creating a seasonal display. Soft light illuminates the scene, highlighting the welcoming aspect of the property.

4.91 out of 5 average rating, 128 reviews

Entire Townhouse -Escape to Door County

FamilyIndoor spacesNearby

4.96 out of 5 average rating, 126 reviews

Home in Egg Harbor

Egg Harbor Escape | Hot Tub | Cedar Sauna | Privac

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Superhost

4.87 out of 5 average rating, 157 reviews

Secluded Home | Walk to Marina + GameRoom & HotTub

FamilyIndoor spacesBathroom

4.86 out of 5 average rating, 205 reviews

Home in Ellison Bay

Northern Lights Farmhouse with Hot Tub

Indoor spacesFamilyView

Superhost

The living area is adorned with a modern light fixture and features a sectional sofa accompanied by two leather armchairs. A round coffee table is centered on a decorative rug. Natural light filters through the windows, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 175 reviews

DoorCo Getaway@Landmark Resort

KitchenFamilyBiking

4.98 out of 5 average rating, 116 reviews

Hot Tub | Sauna | Bar | Arcade | Fire Pit

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Family- and pet-friendly home rentals

4.94 out of 5 average rating, 180 reviews

Cabin in Sister Bay

Wismar Cabin Waterfront- Private Sand Beach

Indoor spacesFamilyCondition

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, 133 reviews

Cozy Cottage in the woods

KitchenFamilySleep quality

4.94 out of 5 average rating, 110 reviews

Home in Egg Harbor

Egg Harbor A-Frame Cabin w/ Lake Access & Sauna

FamilyIndoor spacesCheck-in

4.93 out of 5 average rating, 129 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

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 151 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

Indoor spacesFamilyComfort

4.88 out of 5 average rating, 126 reviews

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

Indoor spacesFamilyAir conditioning

4.86 out of 5 average rating, 147 reviews

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

FamilyKitchenCheck-in

Superhost

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

4.84 out of 5 average rating, 189 reviews

Three Sister's Cottage Barn Retreat

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Family-friendly home rentals with a pool

4.87 out of 5 average rating, 363 reviews

A tri-level condo complex is nestled among lush greenery, showcasing multiple balconies and staircases leading to the main entrance. A pool area is visible in the foreground, where lounge chairs are arranged around a covered pool. The serene landscape adds to the peaceful ambiance.

Condo in Fish Creek

Evergreen Hill B Whirlpool Condo by Pen State Park

KitchenIndoor spacesPool

The living area is furnished with a gray sectional sofa adorned with blue and patterned cushions. A wooden coffee table sits on a textured blue area rug, with a small plant placed on top. The open kitchen is visible in the background, featuring modern appliances and a dining island with seating.

4.88 out of 5 average rating, 188 reviews

Condo Indoor Pool Meadow Ridge #23 Egg Harbor, WI

Indoor spacesFamilyBackyard

4.91 out of 5 average rating, 205 reviews

Townhouse in Egg Harbor

Newly remodeled Indoor pool/hottub Egg Harbor #51

Indoor spacesFamilyCleanliness

4.84 out of 5 average rating, 107 reviews

A spacious living area features a gray sofa adorned with two light blue cushions, paired with a round wooden coffee table. A comfortable armchair is situated nearby. Large windows allow natural light, and a stone fireplace adds to the inviting ambiance.

Townhouse in Egg Harbor

*Indoor Pool * Egg Harbor Townhouse Condo Unit 50.

FamilyIndoor spacesHot tub

4.86 out of 5 average rating, 101 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)

Indoor spacesFamilyBarbecue

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

FamilyKitchenBathroom

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, 41 reviews

Cottage on SisterBay Inn grounds

KitchenIndoor spacesBiking