Holiday rentals in Sister Bay

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Top-rated holiday rentals in Sister Bay

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Guest favourite
A serene lake view is captured at sunset, featuring hues of pink and purple reflecting on the calm water. A private dock is visible in the foreground, accompanied by a small ladder. Soft clouds drift across the sky, enhancing the tranquil atmosphere.
Loft in Ephraim
4.85 out of 5 average rating, 179 reviews

Eagle Harbor Cottage Loft

Eagle Harbor Cottage Loft has glimpses of the Lake from the Loft! It is a renovated, lake-themed apartment/loft (above detached garage) nestled in the woods behind the owner’s main house. Guests have a private entrance and guest parking space. Guests have access to private dock next to the Lake to relax and enjoy sunsets. Two bicycles and 2 kayaks are available for guest use as well. We invite you to spend time refreshing and reflecting on the beauty and peacefulness of the woods and lake.

Top guest favourite
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
4.98 out of 5 average rating, 289 reviews

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).

Top guest favourite
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.
Home in Sister Bay
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!

Top guest favourite
Guest house in Fish Creek
4.96 out of 5 average rating, 276 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 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.
Apartment in Ephraim
4.95 out of 5 average rating, 286 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 favourite
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 favourite
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, 359 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 favourite
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.
Cottage in Sister Bay
4.93 out of 5 average rating, 198 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%).

Top guest favourite
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 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, 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

Top guest favourite
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, 224 reviews

Modern A-Frame, Sister Bay, 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 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
4.99 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.

Popular amenities for Sister Bay holiday rentals

When is the best time to visit Sister Bay?

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Avg. price$293 SGD$273 SGD$319 SGD$302 SGD$368 SGD$460 SGD$637 SGD$609 SGD$454 SGD$476 SGD$359 SGD$372 SGD
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 holiday rentals in Sister Bay

  • Total holiday rentals

    Explore 90 holiday rentals in Sister Bay

  • Nightly prices starting at

    Sister Bay holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,250 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

    90 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!

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