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Holiday houses 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 $187 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Sister Bay holiday rentals include Wi-Fi 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
Home in Sister Bay
5 out of 5 average rating, 31 reviews

SisterBayHus - a Scandi inspired family getaway

Sister Bay Hus has everything you need for an enjoyable vacation in the heart of Door County. Take advantage of the short walk to downtown Sister Bay (and beach!) or simply enjoy seclusion in a quiet neighborhood. Start your day with fika (fee-kah) by enjoying coffee in the sunroom, spend the afternoon on the deck or playing yard games, and end your day with friends and family around the fire pit. Newly furnished 2025 - including new beds, appliances, TVs, furniture, Weber griddle, and more!

FamilyLocationCleanliness

Top Guest favourite
Guesthouse in Fish Creek
4.97 out of 5 average rating, 307 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.

FamilyValueCheckout

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, 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

LocationValueCleanliness

Guest favourite
Condo in Sister Bay
5 out of 5 average rating, 8 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!

ValueLocationAccuracy

Guest favourite
Condo 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"

ValueFamilyLaundry

Top Guest favourite
Cottage in Sister Bay
5 out of 5 average rating, 244 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.

FamilyValueCleanliness

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, 182 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.

FamilyValueAir conditioning

Superhost
Home in Egg Harbor
5 out of 5 average rating, 3 reviews

*New listing-Sunset Escape- hot tub & bay views

*On the bluff overlooking the bay with expansive sunset view *Outdoor hot tub overlooking the bluff *2 Bedrooms (1 King, 1 Queen) *2 Bathrooms *5th Bed is a roll away cot *4 Season Porch *Wooded lot *Fully stocked kitchen *Electric fireplace *Soaking tub in primary bedroom *5 Minutes to Door County Coffee *10 Minutes to Village of Egg Harbor *15 Minutes to Cave Point *Quiet private road, nice for walking

LocationBathroomView

Top Guest favourite
Home in Sister Bay
5 out of 5 average rating, 13 reviews

Modern Sister Bay Retreat | Prime Location

One minute. That’s it. One minute drive to downtown Sister Bay—and yes, you can walk to all your favorite spots too. Coffee, cocktails, waterfront sunsets, shopping, dining—it’s all right there. Then come home to a huge, retro-chic retreat built for groups, games, and late-night fires. Designed to grab your attention and keep you in vacation mode from check-in to check-out..

FamilyLocationQuiet

Superhost
Apartment in Sister Bay
5 out of 5 average rating, 3 reviews

Luxury Downtown Sister Bay Condo - Water Views

Brand New/Modern Downtown Condo – Walk to Everything! Stay in the heart of Sister in this beautifully built condo just steps from beach, shops, restaurants, and the marina/waterfront. The space features 1 large king bed suites, full kitchen, fireplace, and private porch with partial water views. Kids/babies welcome. Pack n' Play and roll out twin bed available.

LocationFamilyComfort

Top Guest favourite
Condo in Sister Bay
4.98 out of 5 average rating, 59 reviews

Door County Dream • Luxe Condo Near the Beach

Welcome to your perfect getaway in the heart of downtown Sister Bay! This newly built, luxurious condo offers a premier short-term rental experience that you won't find anywhere else. With a prime location and direct access to the stunning Sister Bay Beach just steps away, this is the ultimate destination for relaxation and exploration.

ValueLocationCondition

Top Guest favourite
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
4.98 out of 5 average rating, 181 reviews

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. If you're searching for a place to accommodate up to 6 guests, please see our listing - Blue Moon Cabin +2.

LocationFamilySleep quality

Popular amenities for Sister Bay holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Sister Bay's top sights

Sister Bay Beach

41 locals recommend

Sip

28 locals recommend

The Garage

3 locals recommend

Other great holiday rentals in Sister Bay

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, 62 reviews

The Maple House in the Heart of Sister Bay

LocationFamilyOutdoor spaces

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.
Apartment in Sister Bay
4.88 out of 5 average rating, 25 reviews

Alpaca Grand Vacation Rental

FamilyLocationKitchen

Guest favourite
The exterior of the Gothic-arch barn features a curved red façade and a spacious deck adorned with patriotic bunting. Comfortable seating is arranged on the deck, and expansive green fields can be seen in the background under a clear blue sky.
Barn in Sister Bay
4.83 out of 5 average rating, 23 reviews

The Barn at Milkweed Acres

LocationFamilyOutdoor spaces

Guest favourite
A bright living space features large windows that offer natural light and views of the outdoors. The room includes a spacious sectional sofa, accent chairs, a coffee table, and a ceiling fan. Sleek tile flooring enhances the room's open and welcoming feel.
Home in Sister Bay
4.96 out of 5 average rating, 46 reviews

Luxury Remodeled 4BR | Downtown Sister Bay

FamilyLocationTV

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, 81 reviews

Peaceful & Wooded Home - Walk to Sister Bay 0.5m

FamilyLocationKitchen

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.
Apartment in Sister Bay
4.92 out of 5 average rating, 25 reviews

2 Bedroom 2 Bath- The Walkabout

FamilyValueComfort

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, 79 reviews

Walk to Downtown! Wooded 4BR Sister Bay Home

ValueFamilyCleanliness

Top Guest favourite
Home in Fish Creek
5 out of 5 average rating, 9 reviews

Cedar & Glass | Modern Fish Creek Forest Retreat

LocationFamilyAmenities

When is the best time to visit Sister Bay?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$497 NZD$458 NZD$468 NZD$437 NZD$543 NZD$733 NZD$850 NZD$813 NZD$606 NZD$634 NZD$480 NZD$497 NZD
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