Vacation rentals in Sister Bay

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Top-rated vacation rentals in Sister Bay

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Top guest favorite
A quaint cottage stands surrounded by snow-covered trees, with a light grey door and window accents visible. The structure features a simple white exterior, complemented by a winter landscape of freshly fallen snow, creating a serene and peaceful atmosphere.
Guesthouse in Fish Creek
4.96 out of 5 average rating, 274 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 favorite
The living area showcases a light gray couch, a round coffee table with a small plant, and a rocking chair. A flat-screen TV is positioned near a decorative cabinet. The kitchen area is visible in the background, featuring a breakfast counter with seating.
Condo in Ephraim
4.95 out of 5 average rating, 285 reviews

Bright • Cozy • Clean • Condo Near Water • Ephraim

Our bright, clean, cozy, ground-floor condo is just a block from the water in Ephraim. There is 1 bedroom (queen) and a sleeper sofa in the living space (queen). There is a spacious bathroom with shower/tub and large vanity. Shower and toilet area are separate from sink/vanity area. Walk right out onto your own private patio which connects to our spacious yard. Full kitchen w/ stove (small oven/stove), fridge, microwave, toaster, Keurig, cookware, dishes, glassware & dishwasher.

Guest favorite
A private outdoor space is depicted featuring a pergola over a circular stone fire pit area. Surrounding greenery provides a natural backdrop, while patio seating is arranged nearby, inviting relaxation in a serene environment.
Home in Sister Bay
4.9 out of 5 average rating, 115 reviews

Maple Cottage, Cute & Cozy, steps to downtown.

Very cute and cozy home to enjoy Door County from. Large, private back yard with pergola and plenty of patio seating including a fire pit area. Charcoal grill on site. Home is centrally located between Washington Island and Egg Harbor. It's within .4 mile walking distance to downtown Sister Bay. Great place to get away and relax and still have the fun of the restaurants and shops nearby. This is our home away from home and we hope it will be yours too. (Maple Cottage RT-364)

Top guest favorite
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
4.92 out of 5 average rating, 358 reviews

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

Top guest favorite
A cozy studio space is accentuated by a wooden vaulted ceiling. A spacious bed is dressed in light, patterned bedding, while a comfortable couch is positioned beside a small table. Soft lighting from a lamp and an inviting rug contribute to the warm ambiance.
Guest suite in Egg Harbor
4.95 out of 5 average rating, 299 reviews

Cozy Farmhouse Studio

The 16 X 19 foot private studio, is located on the second story of our 120 year old farmhouse and has a private entrance and drive. It is equipped with its own kitchen, bathroom, balcony, queen bed, couch and closet. Our farmhouse is located on five scenic acres adjacent to our pottery studio and gallery. Please be aware that we have no air conditioning. It usually cools off at night, so it’s not typically necessary. We have a ceiling and cooling fan for the hot days.

Guest favorite
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, 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

Guest favorite
A spacious living area features a dining table with six upholstered chairs surrounded by warm, red walls. A cozy seating arrangement includes a pink armchair and a black rocking chair near a fireplace, with large windows allowing natural light to fill the space.
Cottage in Sister Bay
4.96 out of 5 average rating, 126 reviews

The Key to Happiness

Sleeping 4-6 between 4 beds, Plum Retreat provides a one-of-a-kind Door County experience. With 2 large bedrooms (plus giant living room with queen sofa bed, dining area and full kitchen), the 1700 sq-feet have a charming cottage-like feel. Conveniently located with gorgeous perennial gardens, it makes a romantic, peaceful or fun space. Private lawn & patio/grill. Pretty much everything has been thought of. Last summer, all 37 groups of people gave it a 5-star rating!

Guest favorite
The cabin's exterior is characterized by rustic wood siding complemented by vibrant red accents. A welcoming porch is visible at the front, with two rocking chairs inviting relaxation. Surrounding greenery enhances the outdoor space, creating a peaceful atmosphere.
Cabin in Ellison Bay
4.85 out of 5 average rating, 185 reviews

Historic Log Cabin by the Bay (Lake View)

"Doc's Hideaway" sits at the tip of the Door County peninsula in beautiful Gills Rock, surrounded by lush woods on one side and the picturesque Bay and bluffs on the other. This historic mid-1800’s cabin has been lovingly renovated (admire the character of the original hand scraped wood walls and ceiling beams) with all the amenities and comforts of home. New in 2022: extra fast Wifi via Starlink (up to 105 mbps) and a high efficiency ductless AC and heating system.

Guest favorite
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
5 out of 5 average rating, 221 reviews

Sister Bay A-Frame | 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.

Top guest favorite
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
4.99 out of 5 average rating, 158 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.

Top guest favorite
Cottage in Sturgeon Bay
4.96 out of 5 average rating, 383 reviews

Sturgeon Bay Waterfront Cottage, Private beach.

Waterfront guest cottage on Door County's Gold Coast! Nestled among luxury homes, this quaint 1930's cottage has undergone an interior renovation while preserving its character on the outside. Two bedroom, one full bath, stocked kitchen, living room. Located steps from the bay with a private beach. Hear the gentle sound of waves lapping on the shore as you sleep. Bring your kayak and fishing poles. Perfect for anyone seeking a quiet retreat!

Guest favorite
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
4.95 out of 5 average rating, 129 reviews

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

Popular amenities for Sister Bay vacation rentals

When is the best time to visit Sister Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ845ﺩ.ﺇ786ﺩ.ﺇ918ﺩ.ﺇ870ﺩ.ﺇ1,061ﺩ.ﺇ1,326ﺩ.ﺇ1,836ﺩ.ﺇ1,755ﺩ.ﺇ1,307ﺩ.ﺇ1,370ﺩ.ﺇ1,036ﺩ.ﺇ1,072
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.

Quick stats about vacation rentals in Sister Bay

  • Total vacation rentals

    Explore 90 vacation rentals in Sister Bay

  • Nightly prices starting at

    Sister Bay vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 4,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Sister Bay vacation 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!

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  5. Sister Bay