Photo by Richard Remington

Sister Bay holiday lettings

We found 755 holiday rentals — enter your dates for availability

Select from 82 houses, 28 flats and other holiday rentals to find the perfect place for your stay in Sister Bay. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and air conditioning. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Sister Bay

Showing deals for:5 Jun - 12 Jun

Image gallery for The Lookout, near Sister Bay with Starlink internet

Welcome to the lookout!
10 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

The Lookout, near Sister Bay with Starlink internet

Ellison Bay

7% off
Price is £4,247
for 7 nights, 1 home
£607 per night
includes taxes & fees
The Lookout, near Sister Bay with Starlink internet

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Why people love visiting friendly Sister Bay

The area's wineries and festivals are just some of the reasons to come on holiday to Sister Bay. This city's shopping, restaurants and hiking attract many visitors, as does its welcoming and walkable location. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Sister Bay

Do you want to find things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Sister Bay a one-of-a-kind holiday spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Peninsula State Park Golf Course (4.3 mi / 6.9 km)
  • Stone's Throw Winery (9.8 mi / 15.8 km)
  • Cave Point County Park (17.9 mi / 28.8 km)
  • Whitefish Dunes State Park (18.7 mi / 30.1 km)
  • The Orchards at Egg Harbor (10.7 mi / 17.2 km)
  • Alpine Resort Golf Course (13.2 mi / 21.2 km)

Exploring the natural landscape of Sister Bay

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Sister Bay. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Waterfront Park (0.2 mi / 0.3 km)
  • Sister Bay Beach (0.2 mi / 0.3 km)
  • Ephraim Public Beach (3.7 mi / 6 km)
  • Nicolet Bay Beach (5.2 mi / 8.4 km)
  • Fish Creek Public Beach (7.3 mi / 11.7 km)
  • Kangaroo Lake (10.8 mi / 17.5 km)

Frequently asked questions

What is the best area to stay in Sister Bay when booking a holiday rental?
When considering a holiday rental in Sister Bay, Wisconsin, the charming downtown area is often regarded as the best option for visitors. This vibrant neighbourhood offers a delightful mix of shops, restaurants, and scenic views of the bay, making it an ideal base for exploring the region. One of the top attractions in this area is the picturesque Sister Bay Marina, where you can enjoy water activities or simply take in the stunning vistas. Additionally, the nearby Sister Bay Park provides a lovely spot for picnics and leisurely walks along the waterfront.

Another appealing location for a holiday rental is the north end of Sister Bay, which boasts a more tranquil atmosphere. This area is close to the famous Al Johnson's Swedish Restaurant, known for its iconic grass-covered roof and delicious Swedish cuisine. With a variety of properties available, from quaint cottages to modern condos, visitors can find the great accommodation to suit their needs.
How much does it cost to rent a holiday home in Sister Bay?
Prices for holiday rentals in Sister Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sister Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Sister Bay holiday house rentals?
You can find great discounts on house rentals in Sister Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Sister Bay?
For renting a beach house in Sister Bay, look towards the picturesque waterfront along the shores of Green Bay. The area around Sister Bay Marina offers holiday rentals that provide stunning views of the water, with many properties featuring amenities such as private decks, outdoor grilling areas, and fire pits, superb for enjoying the serene sunsets.

Properties in this vicinity often include family-friendly amenities like spacious living areas, fully equipped kitchens, and easy access to sandy beaches, making them ideal for gatherings. Additionally, the nearby Sister Bay Park provides a lovely setting for picnics and recreational activities, while the local shops and restaurants in the village centre add to the convenience for guests.

Further along the shoreline, the areas near Northport and the scenic Door County Coastal Byway offer charming cottages and larger homes that frequently come with amenities like kayaks, bicycles, or access to shared private beaches. These rentals are superb for those looking to explore the natural beauty of Door County, with opportunities for hiking and boating nearby.
What is the most popular type of holiday rental accomodation in Sister Bay?
In Sister Bay, holiday houses are the most popular type of holiday rental, with approximately 312 available in the area. These homes are often situated near the picturesque waterfront and provide ample space for families or groups, featuring multiple bedrooms, fully equipped kitchens, and spacious living areas. Many also include outdoor decks or patios, superb for enjoying the scenic views of Door County. Condos are another popular option, with around 112 properties offering convenient locations close to local shops and restaurants, often equipped with amenities like pools and fitness centres. Additionally, there are about 64 cottages and 24 cabins, which provide a charming, rustic experience for those looking to immerse themselves in nature.
Are there any family house rentals in Sister Bay?
In Sister Bay, Wisconsin, there are numerous family-friendly holiday rentals available, with around 107 options to choose from. This charming village in Door County is known for its picturesque waterfront and abundance of outdoor activities, making it an excellent choice for families.

Visitors will find properties that often feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play. Many rentals include amenities such as Wi-Fi, air conditioning, and sometimes even fire pits for cosy evenings under the stars.

Sister Bay is close to various attractions, including the beautiful beaches of the bay itself and the scenic hiking trails in nearby state parks. Families can also enjoy local parks, playgrounds, and the vibrant setting of the village, which hosts seasonal festivals and events.
Can I rent a holiday home with a pool or hot tub in Sister Bay?
In Sister Bay, Wisconsin, there are several holiday homes available for rent that feature pools and hot tubs, making it an excellent choice for travellers seeking relaxation and recreation. This charming village, located on the scenic Door County peninsula, offers a variety of accommodations, including spacious family homes and cosy cottages. Many of these properties come equipped with private pools, hot tubs, outdoor patios, and fully stocked kitchens, ensuring a comfortable stay.

Sister Bay itself is known for its beautiful waterfront, local shops, and restaurants, allowing visitors to enjoy both the tranquility of nature and the vibrancy of community life. Additionally, the nearby parks and beaches provide opportunities for outdoor activities, with some rentals offering easy access to these scenic spots.
Can I find long-stay holiday rentals in Sister Bay?
A long-stay holiday rental in Sister Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Sister Bay?
In Sister Bay, there are numerous pet-friendly house rentals available, with around 42 options to choose from, making it a great destination for travellers looking to bring their furry friends along. Many of these holiday rentals offer comfortable amenities such as fully equipped kitchens, outdoor spaces for relaxation, and spacious living areas suitable for both pets and their owners.

The area is known for its charming waterfront and scenic views, with several properties located near the beautiful Sister Bay Beach, where you and your pet can enjoy leisurely walks along the shore. Additionally, nearby parks and nature trails provide ample opportunities for outdoor activities, superb for exploring with your pet.
Are there any remote work holiday rentals in Sister Bay?
In Sister Bay, Wisconsin, there are numerous remote work holiday rentals available, with around 500 options to choose from. This charming village, located along the scenic Door County coastline, provides a great backdrop for those looking to combine work and leisure. Many of the properties come equipped with reliable Wi-Fi, ensuring that remote workers can stay connected while enjoying the beauty of the area.

Travellers can expect a variety of amenities tailored for comfort and productivity, such as dedicated workspaces, fully equipped kitchens for preparing meals, and inviting living areas for relaxation after a day of work. Some rentals also feature outdoor spaces, allowing guests to take breaks amidst the natural beauty of the surroundings.

Sister Bay offers a delightful mix of activities, from exploring local parks and beaches to enjoying nearby shops and restaurants. The area is known for its picturesque landscapes, making it an excellent choice for those seeking inspiration while working remotely. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Sister Bay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Sister Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Sister Bay?
In Sister Bay, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the scenic surroundings. A fireplace is a common amenity, adding a cosy touch to the accommodations, especially during cooler months. Onsite parking is available for convenience, making it easy for visitors to explore the area. Additionally, most rentals come with coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Sister Bay for a holiday rental?
The best time to visit Sister Bay for a holiday rental is during the peak season from June to August. This period is particularly popular, with July being the standout month, as visitors flock to enjoy the stunning waterfront views, vibrant local events, and the charming atmosphere of the Door County area. The warm weather, with temperatures typically ranging from 15 to 25 degrees Celsius, creates ideal conditions for outdoor activities such as hiking, boating, and exploring the picturesque beaches.

During the summer months, Sister Bay comes alive with a variety of festivals and activities, making it a superb destination for families and groups looking for fun and adventure. You can enjoy live music, local art shows, and delicious farm-to-table dining, all while soaking in the beautiful surroundings.

For those seeking a more budget-friendly option, consider visiting in November. While this month sees fewer tourists, it offers a unique chance to experience the tranquillity of Sister Bay in the off-season. You can appreciate the peaceful scenery and engage in a slower pace of life, which can be quite refreshing.

Ultimately, your choice of when to visit Sister Bay should align with your preferences for lively summer activities or the serene beauty of a quieter time.
How early should I book a Sister Bay holiday rental?
Book your Sister Bay holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Sister Bay?
In Sister Bay, visitors can enjoy a variety of attractions that showcase the charm of this picturesque village. The waterfront area along Sister Bay features a lovely marina where travellers can indulge in boating and fishing activities. The nearby Sister Bay Beach offers sandy shores and a family-friendly atmosphere, superb for swimming and picnicking in the warmer months.

For a taste of local culture, the Sister Bay Historical Society provides insights into the area's history and heritage, while the nearby Door County Creamery is a delightful stop for cheese lovers, offering a range of artisanal cheeses and local products.

Nature enthusiasts will appreciate the stunning views and hiking opportunities at the nearby Peninsula State Park, which boasts scenic trails, lookout points, and the beautiful Nicolet Bay.
Can I change or cancel my Sister Bay home rental booking on Vrbo?
To find Sister Bay holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Sister Bay holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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