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Holiday rentals in Sister Bay

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Quick stats about holiday rentals in Sister Bay

  • Total holiday rentals

    Explore 100 holiday rentals in Sister Bay

  • Nightly prices starting at

    Sister Bay holiday rentals start at £83 per night before taxes and fees

  • Verified guest reviews

    Over 4,260 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    100 of Sister Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Sister Bay rentals

  • 4.8 Average rating

    Sister Bay stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Sister Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The spacious living area features a large sectional sofa adorned with decorative cushions, surrounded by polished hardwood floors. A modern coffee table sits at the center, while a dining area with a long table and black chairs is visible in the background. Natural light streams through the windows.
Home in Sister Bay
4.97 out of 5 average rating, 60 reviews

The Maple House in the Heart of Sister Bay

Prime location! Walk to everything! Newly remodeled house near the best of everything Sister Bay has to offer. A short and easy walk to the public beach, Al Johnson’s, Wild Tomato Pizza, CHOP, Husby’s, Sister Bay Bowl, shopping and much much more! You will find this 4BR/3.5 bath home well stocked and full of amenities. Enjoy the wood burning fireplace in the living room or relax in the lower level rec room. Have a beverage on the covered porch before walking to dinner. This home is a must stay!

Top guest favourite
Guest house in Fish Creek
4.97 out of 5 average rating, 305 reviews

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.

Top guest favourite
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.
Home in Sister Bay
4.96 out of 5 average rating, 101 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.

Guest favourite
Home in Fish Creek
5 out of 5 average rating, 7 reviews

Cedar & Glass | Modern 5-Acre Luxury Forest Home

Cedar & Glass is a custom-designed architectural retreat where modern design and nature exist in perfect harmony. This 3-bedroom, 2.5-bath luxury escape features soaring floor-to-ceiling glass, heated concrete floors, a sculptural fireplace, and curated interiors that blur the line between indoors and out. Set on five private wooded acres just minutes from Fish Creek, guests enjoy rare seclusion, refined comfort, outdoor dining, and evenings around the fire under the trees.

Guest favourite
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.
Home in Sister Bay
4.91 out of 5 average rating, 123 reviews

Cozy Cottage in the woods

New Renovations Jan 25: Windows, New Wall Unit AC, Updated Bathroom. Welcome to Hydrangea Haven. A cozy (1200 square ft) cottage tucked away on a quiet peaceful road, but close to all the fun. Nestled 3 miles north of sister bay, between Sister Bay and Ellison Bay. Bike down the low traffic beach road to all that downtown Sister Bay has to offer. Cozy up with the indoor fireplace, Adirondack chairs around the outdoor fire pit. NOTE: we are a 10 min DRIVE to beach not walk.

Guest favourite
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.
Home in Sister Bay
4.89 out of 5 average rating, 300 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

Guest favourite
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
4.99 out of 5 average rating, 119 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.

Guest favourite
Apartment in Sister Bay
5 out of 5 average rating, 5 reviews

Pearl Of Sister Bay Luxury Downtown Condo

Welcome to the Pearl of Sister Bay,a chic downtown condo ideal for a relaxing escape! This 1-bedroom, 1-bathroom condo offers modern comforts and design. Condo , has a fully equipped kitchen with a stove and refrigerator, fireplace, deck with a partial water and village view. Located in the heart of Sister Bay, you’ll be steps from the beach, local bars and restaurants, shopping and local attractions. Relax, recharge, and enjoy the charm of this vibrant destination!

Guest favourite
Apartment in Sister Bay
5 out of 5 average rating, 111 reviews

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"

Top guest favourite
Cottage in Sister Bay
5 out of 5 average rating, 242 reviews

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.

Guest favourite
A bright living area features large windows that allow natural light to fill the space. A comfortable armchair and small lamp are positioned beside the window, while a patterned sofa adds a touch of color. A large TV is mounted above an elegant fireplace.
Flat in Sister Bay
4.88 out of 5 average rating, 24 reviews

Alpaca Grand Vacation Rental

The Alpaca Grand Vacation in Sister Bay, WI, offers a unique stay above Alpaca to Apparel in a charming early 1900s building with hardwood floors and alpaca accents. Enjoy an outdoor entertainment space with a gas fire pit, a sunroom with a 75-inch TV, and a cozy living room with a 65-inch TV and gas fireplace. With three bedrooms and a full kitchen, this rental blends historic character with modern comforts, creating a memorable Door County getaway.

Top guest favourite
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
4.98 out of 5 average rating, 179 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.

Popular amenities for Sister Bay holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Sister Bay

Superhost
A broad deck overlooks the serene waters of Green Bay, featuring a striped awning providing shade. The calm surface of the water reflects the sky, while rocky beach areas are visible below. Surrounding trees frame the tranquil view, enhancing the natural setting.
Cottage in Sister Bay
4.78 out of 5 average rating, 78 reviews

Sister Bay Rental- Water Front Cottage

Guest favourite
Apartment in Sister Bay
5 out of 5 average rating, 10 reviews

Marina Views & Walkable Sister Bay Retreat

Guest favourite
An outdoor patio area features a wooden table surrounded by four chairs, with blue cushions adding a pop of color. Decorative plants are positioned on the table and in a pot, while a textured area rug enhances the space's inviting feel.
Flat in Sister Bay
4.92 out of 5 average rating, 24 reviews

2 Bedroom 2 Bath- The Walkabout

Guest favourite
A spacious, open-concept kitchen and dining area is displayed, featuring modern appliances and ample natural light. A dining table with white chairs is positioned centrally, while a sliding glass door leads to a deck. A cozy living area is visible, inviting relaxation.
Home in Sister Bay
4.81 out of 5 average rating, 79 reviews

Peaceful & Wooded Home - Walk to Sister Bay 0.5m

Top guest favourite
Home in Ellison Bay
4.97 out of 5 average rating, 29 reviews

Humbug Abode

Top guest favourite
An outdoor seating area features four blue chairs arranged around a stone fire pit with stacked firewood. The backdrop includes a wooded environment and part of the cottage, visible through the trees. Sunlight filters through the leaves, creating a natural ambiance.
Home in Sister Bay
4.94 out of 5 average rating, 78 reviews

Walk to Downtown! Wooded 4BR Sister Bay Home

Top guest favourite
Home in Sister Bay
5 out of 5 average rating, 30 reviews

SisterBayHus - a Scandi inspired family getaway

Top guest favourite
The Round Haüs features a circular structure surrounded by lush greenery, with neatly trimmed shrubs and trees enhancing the landscape. A sunset is reflected through the large windows, while a cozy outdoor seating area with white chairs is visible in the foreground.
Home in Ephraim
5 out of 5 average rating, 35 reviews

Round Haüs - Panoramic Views

When is the best time to visit Sister Bay?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price£219£202£206£178£217£271£375£359£267£280£212£219
Avg. temp-8°C-6°C0°C7°C14°C19°C21°C20°C16°C9°C2°C-4°C

Frequently Asked Questions

  • What are the best places to stay in Sister Bay?

    Sister Bay has vacation rentals, cozy cabins, and boutique inns, many situated near the waterfront or nestled in peaceful wooded areas. Staying close to the bay allows easy access to shops and local dining.

  • What are the best things to do in Sister Bay with kids?

    Explore waterfront parks, enjoy sandy beaches along the bay, and visit local ice cream shops for a sweet treat. Families can discover interactive museum exhibits or join sightseeing boat rides for lake views.

  • What are some of the best things to do in Sister Bay?

    Stroll waterfront boardwalks, taste locally made foods, and relax on sandy village beaches. Sister Bay has friendly shops, kayaking, and regular live music events along the marina.

  • How is the weather in Sister Bay?

    Sister Bay has cold winters around 11–26°F (-12 to -4°C) and warm summers with highs near 77–81°F (25–27°C). Spring and autumn bring brisk winds and changing temperatures, so pack layers.

  • When is the best time to visit Sister Bay?

    Late spring through early fall is often recommended for warmer temperatures and outdoor activities, with popular harvest and blossom events. Winter visits have quiet village charm with access to snowy nature.

  • What are the best places to visit in Sister Bay?

    Explore the waterfront marina, see locally owned galleries, and stroll boardwalks along the bay. Waterfront parks and traditional cherry orchards are often recommended for visitors.

  • What are some hiking trails in Sister Bay?

    Explore forested walking paths, coastal trails along the bay, and nature preserves near Sister Bay. Trails may feature lake views, wildflower meadows, and opportunities for birdwatching.

  • What are some family activities we can do in Sister Bay?

    Families can swim at sandy beaches, rent paddle boats, and explore interactive exhibits at local museums. Seasonal festivals and open-air concerts are often a highlight for all ages.

  • What are some of the best day trip ideas from Sister Bay?

    Venture to nearby nature preserves, visit historic lighthouse sites, or explore local art towns around Door County. Regional state parks are often recommended for hiking and picnicking.

  • Are there any pet friendly accommodations available in Sister Bay?

    Sister Bay has pet friendly vacation rentals and some inns, with easy access to outdoor trails and parks for walks. Always check individual property policies for details during booking.

  • What are some local tips for visiting Sister Bay?

    Locals recommend trying fresh cherry treats, arriving early to waterfront areas for peaceful views, and visiting farmers markets for regional products. Layer clothing in spring and fall for changing weather.

  • What is Sister Bay known for?

    Sister Bay is known for its scenic shoreline, waterfront dining, and friendly village atmosphere. The area has vibrant community events, cherry orchards, and access to Lake Michigan’s natural beauty.

  • What are the best hidden gems to explore in Sister Bay?

    Seek out tucked-away local art galleries and visit quieter nature preserves around Sister Bay. Small family-run eateries and roadside farm stands are frequently suggested for a taste of the local scene.

  • What are the best foods to try in Sister Bay?

    Try locally made cherry pies, fresh whitefish from Lake Michigan, and Wisconsin cheese dishes. Seasonal farmer’s markets and classic supper clubs feature regional specialties.

  • What should I bring for a trip to Sister Bay?

    Pack layers, as temperatures change between cool mornings and warmer afternoons throughout the year. Comfortable walking shoes, a swimsuit for summer visits, and a light jacket or raincoat are frequently suggested.

  • What is the nightlife in Sister Bay like?

    Sister Bay has a laid-back nightlife, with casual bars, local taverns, and live music venues near the waterfront. Evenings often feature local musicians and relaxed lakeside atmospheres.

  • What are the most popular events or festivals in Sister Bay?

    Sister Bay has a classic car show and community fireworks, especially around summer holidays. The fall harvest festival is frequently suggested for local traditions and seasonal food.

  • Are there family friendly vacation rentals in Sister Bay?

    Sister Bay has a range of family friendly vacation rentals, including spacious cabins, lakeside homes, and multi-bedroom apartments. Many are near local parks and village amenities.

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Door County
  5. Sister Bay