Family-friendly holiday rentals in Sister Bay

4.87 out of 5 average rating, 322 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.

Apartment in Fish Creek

Evergreen Hill B Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! All 3 B rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

4.92 out of 5 average rating, 144 reviews

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.

Cottage in Sister Bay

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.

4.98 out of 5 average rating, 289 reviews

A cozy studio bedroom features a spacious bed with stylish bedding and decorative pillows. Light streams through a window covered with plantation blinds. Two lamps illuminate the space beside the bed, while a gray upholstered bench sits at the foot, complementing the wood-look flooring.

Flat in Fish Creek

Night Cap Studio Loft in Downtown Fish Creek

In the heart of Fish Creek, above our bustling Hat Head shop, enjoy your stay in our newly remodeled second story studio loft. Complete with studio bedroom, bath, kitchen with new appliances, sitting room, and private balcony deck. Enjoy walking distance to the beach, shops, restaurants, Peninsula State Park, and more. Close to the action, yet a great hideaway for privacy and relaxation. Bright and cheery, modern, simply stated, and clean. For adult single or couple. (Sorry no pets or kids).

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, 107 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!

4.92 out of 5 average rating, 359 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

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, 284 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

4.99 out of 5 average rating, 108 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.

5 out of 5 average rating, 108 reviews

Apartment 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"

5 out of 5 average rating, 224 reviews

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.

Cottage in Sister Bay

Sister Bay A-Frame Cabin, Coffee Bar, Fireplace

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.

4.99 out of 5 average rating, 159 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.

4.95 out of 5 average rating, 111 reviews

The image shows a well-lit open-concept living area and kitchen. A sink and dishwasher are visible in the kitchen, with a microwave on the counter. A cozy seating area features a light gray armchair and a side table, with large windows allowing natural light.

Apartment in Ephraim

In the Heart of Ephraim ~ Cozy Condo

First floor, accessible 1-bedroom condo. Spacious bathroom with newly tiled shower, two flat screen smart TVs with cable. Full kitchen has new appliances (fridge, stove, oven and dishwasher), quartz countertops, microwave, drip coffee maker + toaster. Private patio connects to spacious shared yard with gazebo, patio table + chairs, grills and lovely water fountain (only runs in late spring and summer). Centrally located to everything in Door County!

The exterior of the two-story home features a wraparound porch, framed by lush greenery and a manicured lawn. A large deck is visible, providing ample outdoor seating for relaxation. The inviting light-colored siding and gabled roof create a classic and welcoming appearance.

4.88 out of 5 average rating, 107 reviews

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

The Goat and Cherry by Getaway and Stay Make family memories at this 4BR, 2.5BA Sister Bay winter retreat! Vaulted ceilings and natural light create a cozy space for snow-filled days. Kids and adults will love the hot tub, fire pit, and covered porch for cocoa and stargazing. Just minutes from Door County winter trails and attractions, this home is perfect for family fun, relaxation, and a magical snowy getaway.

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

4.91 out of 5 average rating, 191 reviews

A spacious living area is highlighted by a large sectional sofa, accented with decorative pillows. A flat-screen TV is mounted above a stone fireplace. Natural light pours in through two large windows, enhancing the welcoming ambiance of the space.

Townhouse in Egg Harbor

Indoor pool and hottub Egg Harbor condo #51

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, 178 reviews

Condo Indoor Pool Meadow Ridge #23 Egg Harbor, WI

4.87 out of 5 average rating, 102 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

4.97 out of 5 average rating, 137 reviews

The exterior of a house is set against a backdrop of tall trees, showcasing a spacious lawn. A selection of wooden chairs surrounds a fire pit area, providing an inviting space for outdoor gatherings. The house features multiple levels, with a large deck visible.

Home in Sturgeon Bay

Modern Door County Waterfront House + Hot Tub

Superhost

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.

4.91 out of 5 average rating, 204 reviews

DoorCo Happy Place @Landmark Resort

4.92 out of 5 average rating, 162 reviews

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.

Cabin in Egg Harbor

Green Apple Lodge (w/hot tub & hi-speed wifi!)

4.94 out of 5 average rating, 31 reviews

An inviting outdoor pool area features a sparkling blue pool and a relaxing hot tub. Surrounding lounge chairs and tables offer a place to unwind, while the well-maintained landscaping provides a serene backdrop. The townhome structure can be seen in the distance.

Apartment in Fish Creek

Fish Creek Condo - Walk to Shopping, Dining & Park

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, 112 reviews

Entire Townhouse -Escape to Door County

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 199 reviews

A spacious kitchen and dining area features modern appliances and wooden cabinetry. A wooden dining table is accompanied by comfortable chairs. Natural light floods the room through large windows, revealing a view of the greenery outside, enhancing the connection to nature.

Home in Egg Harbor

The Hein Cottage-Beautiful hideaway in the ❤️of DC

Superhost

The exterior of the cottage showcases a spacious wrap-around porch, elevated on a stone foundation. The home is surrounded by a grassy area, with trees providing a natural backdrop. Large windows invite plenty of natural light into the interior spaces.

Cottage in Sturgeon Bay

4.77 out of 5 average rating, 120 reviews

The Bungalow at Potawatomi State Park

4.97 out of 5 average rating, 121 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.

Flat in Egg Harbor

The Loft – Pet-Friendly Egg Harbor Rental

4.85 out of 5 average rating, 136 reviews

A comfortable outdoor seating area is presented with dark wicker chairs and matching ottomans, featuring colorful cushions. The white deck overlooks a serene bay, with a peaceful water view and distant shoreline visible under a clear blue sky.

Cabin in Sturgeon Bay

..you can Fish right off your own Private dock.

4.91 out of 5 average rating, 299 reviews

A lakeside view is captured, featuring a wooden swing under a shaded structure. Tall trees frame the scene on either side, with the water reflecting a clear blue sky. A gentle breeze seems to rustle the leaves, enhancing the peaceful ambiance.

Cottage in Washington

Gull Cottage Waterfront Home on Washington Island

Farm stay in Baileys Harbor

A two-story farmhouse is nestled in a lush green landscape, surrounded by trees. The structure features a light blue exterior and a welcoming front porch. A gravel path leads up to the house, providing access from the nearby road.

4.84 out of 5 average rating, 184 reviews

Heart of the Door Homestead (Walking Trails)

A cozy living area features a comfortable blue sofa with decorative pillows and a light-colored accent chair. A wooden coffee table sits in the center, while large windows offer views of the outdoors. A television is positioned on a console table, enhancing the inviting space.

4.9 out of 5 average rating, 115 reviews

Family Friendly Retreat in the Heart of Sister Bay

The remodeled farmhouse is showcased with a welcoming front porch and manicured landscaping. A large tree provides shade in the front yard, while a flag flutters gently. A rustic barn is visible in the background, surrounded by lush greenery and blooming orchards.

4.88 out of 5 average rating, 106 reviews

Swedish Orchard Farm

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 40 reviews

A serene landscape features a one-acre pond surrounded by lush greenery and colorful autumn foliage. A charming barn and the main lodge are visible in the distance, creating a harmonious blend with the natural setting.

Barn in Wallace

Pinewood Springs Lodge, 240 acres with 1 acre pond

4.93 out of 5 average rating, 14 reviews

A spacious living area features a large, L-shaped sectional sofa in a soft gray hue, complemented by a square ottoman. Natural light fills the space through multiple large windows overlooking the green landscape. A dining area is visible in the background with table seating.

Home in Sturgeon Bay

Door County Agrotourist Retreat

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, 94 reviews

Spacious Private Condo + Indoor Pool!

4.82 out of 5 average rating, 97 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.

A dining area is furnished with a wooden table and six chairs, positioned on a textured rug. The open layout connects to a bright kitchen, with soft lighting highlighting modern cabinetry. Natural light filters through the window, enhancing the inviting atmosphere.

4.85 out of 5 average rating, 71 reviews

Updated Townhouse Condo with Indoor Pool & Hot Tub

Superhost

A spacious living area features a high, vaulted ceiling with exposed beams. A stone fireplace serves as a focal point, complemented by bright artwork above. Large windows allow natural light, while comfortable seating is arranged for relaxation.

Home in Egg Harbor

4.74 out of 5 average rating, 23 reviews

The Cottage Condo in Charming Egg Harbor

4.97 out of 5 average rating, 36 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