Holiday houses in Sister Bay

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Top-rated holiday rentals in Sister Bay

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Guest favourite
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.
Condo in Fish Creek
4.86 out of 5 average rating, 318 reviews

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 4 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.

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.
Apartment in Fish Creek
4.98 out of 5 average rating, 287 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 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
4.97 out of 5 average rating, 268 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.
Condo in Ephraim
4.95 out of 5 average rating, 283 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.

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.

Top Guest favourite
The entrance is framed with natural wood siding and features a double glass door adorned with a festive wreath. Two wooden benches are placed on either side of a gravel pathway, complemented by greenery and decorative lighting fixtures.
Home in Baileys Harbor
4.99 out of 5 average rating, 176 reviews

Winding Down - A Retreat on the "Quiet Side"

Enjoy the fall & winter season! We still have availability for the up coming Christkindlmarket in Sister Bay & Fish Creek Winterfest in January. Get ready to relax and recharge with family & friends. Winding Down is the perfect place to enjoy the quiet side of DC. We are walking distance from the Nature Preserve & the shores of North Bay. Located in a beautiful cedar forest that provides a needed respite. Plenty of privacy but also a short drive to Ephraim & Sister Bay.

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

Guest favourite
Condo in Sister Bay
5 out of 5 average rating, 107 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"

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, 215 reviews

Beechwood Cottage | Sister Bay A-Frame | 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, 155 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.

Guest favourite
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.
Home in Sister Bay
4.9 out of 5 average rating, 115 reviews

Family Friendly Retreat in the Heart of Sister Bay

Our charming, Swedish-style chalet is located on the main drag, on the north side of Sister Bay. You and your group will love walking into town for a trip to the beach and park or a meal at any of Sister Bay's fine restaurants and coffee shops. Or just relax on our front deck and read a book, enjoy a beverage and watch the busy hustle and bustle of Door County. Our cottage is perfect for couples, families (with kids) and people traveling with pets.

Guest favourite
A comfortable living area features a gray sofa and a patterned armchair. Natural light fills the space through large windows adorned with navy blue curtains. A coffee table sits centrally, and a television is positioned on a wooden unit next to an air conditioning unit.
Condo in Ephraim
4.9 out of 5 average rating, 166 reviews

Ephraim Stay Near Water | Fireplace | Unit # 102

Enjoy a cozy and quiet escape just two blocks from the water in the heart of Ephraim. Located on the first floor, this spacious unit features a queen bed, sofa bed, kitchen with all the essentials, and bathroom, providing everything you need for a comfortable stay. We include WiFi, cable, coffee, towels, linens, and more. Relax in the peaceful backyard or take a short walk to restaurants, shops, and the lake. A perfect spot to explore Door County!

Popular amenities for Sister Bay holiday rentals

When is the best time to visit Sister Bay?

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Avg. price$344 AUD$320 AUD$374 AUD$354 AUD$432 AUD$540 AUD$748 AUD$715 AUD$532 AUD$494 AUD$366 AUD$383 AUD
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 $60 AUD 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 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

    90 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!

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