Photo by Wendy Stokes

Sister Bay holiday lettings

We found 773 holiday rentals — enter your dates for availability

Select from 81 houses, 29 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:26 Dec - 2 Jan

Image gallery for Red Cherry Woods Cottage 🍒 New Construction!

Red Cherry Woods Upscale Retreat in Baileys Harbor Quiet Wooded Neighborhood
10 out of 10, Exceptional, (77 reviews)
Exceptional
(77 reviews)

Red Cherry Woods Cottage 🍒 New Construction!

Baileys Harbor, WI

7% off
Price is £1,770
for 7 nights, 1 cottage
£253 per night
includes taxes & fees
Red Cherry Woods Cottage 🍒 New Construction!

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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    More space, more privacy, more amenities — more value

Find out more about Sister Bay

Find out more about Sister Bay

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)
  • Egg Harbor Fun Park (13.8 mi / 22.2 km)
  • Cave Point County Park (17.9 mi / 28.8 km)
  • Whitefish Dunes State Park (18.7 mi / 30.1 km)
  • Stone's Throw Winery (9.8 mi / 15.8 km)
  • The Orchards at Egg Harbor (10.7 mi / 17.2 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)
  • Eagle Harbor (3.5 mi / 5.6 km)
  • Ephraim Public Beach (3.7 mi / 6 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 looking for the ideal area to stay in Sister Bay, Wisconsin, one of the most favourable options is the waterfront area. This picturesque location offers stunning views of the bay and easy access to sandy beaches, making it superb for those who enjoy outdoor activities. Here, you can find a variety of holiday rentals, ranging from charming cottages to modern condos, with many properties benefiting from proximity to the water.

Staying near the waterfront also places you close to attractions such as Sister Bay Marina, where you can rent boats or kayaks for a day on the water. The nearby Sister Bay Park is a delightful spot for picnics and leisurely strolls, featuring playgrounds and lovely picnic areas. Additionally, the vibrant local dining scene is just a stone's throw away, allowing you to indulge in delicious meals at various restaurants that celebrate the region's culinary offerings.

Another appealing area is the village centre, which is bustling with shops, galleries, and eateries. This neighbourhood is particularly lively during the summer months, with various events and festivals showcasing local culture. The proximity to attractions like the historic Sister Bay Ice Cream Factory and the charming shops along the main street adds to the allure, providing plenty of options for entertainment and exploration.
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, Wisconsin, the area around Sister Bay itself is an excellent choice. This charming village is located along the scenic shoreline of Door County and offers a variety of holiday rentals with easy access to beautiful sandy beaches. Properties here often feature amenities such as private decks with views of the bay, outdoor grills for summer barbecues, and spacious living areas ideal for family gatherings.

The waterfront park in Sister Bay is a popular spot, where visitors can enjoy swimming, kayaking, or simply relaxing by the water. Many beach houses in this area are within walking distance to local attractions, including shops, restaurants, and the iconic Sister Bay Marina, which is superb for those interested in boating or fishing.
What is the most popular type of holiday rental accomodation in Sister Bay?
In Sister Bay, holiday houses are the most popular type of rental accommodation, with around 78 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the serene surroundings. Additionally, there are about 28 condominiums and 16 cottages, which offer similar amenities but in a more compact form, appealing to couples or smaller parties. Cabins and apartments are also available, providing a rustic or convenient option for those wanting a different experience.
Are there any family house rentals in Sister Bay?
In Sister Bay, Wisconsin, there are numerous family-friendly house rentals available, with around 104 options to choose from. This charming village, located along the scenic Door County coastline, is great for families looking to explore the beauty of the area. Many of these properties offer spacious living areas, full kitchens for easy meal preparation, and outdoor spaces ideal for children to play. Visitors can also expect amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay.
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 come with pools or hot tubs, making it a delightful choice for those looking to enjoy some relaxation during their stay. This charming village, located along the scenic Door County coastline, offers a range of properties in close proximity to beautiful waterfront views and local attractions.
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 a number of pet-friendly house rentals available, offering a welcoming environment for travellers with furry companions. Many of these properties come equipped with amenities that cater to both pets and their owners, including spacious yards, outdoor seating areas, and easy access to nearby parks for walks and playtime.

The area surrounding Sister Bay is known for its picturesque waterfront and charming village atmosphere, making it an excellent choice for those looking to enjoy nature with their pets. Local parks, such as Sister Bay Beach, provide ample opportunities for outdoor activities, where pets can enjoy the fresh air and open space. Additionally, the nearby Door County Scenic Byway offers scenic driving routes and opportunities for hiking with pets.
Are there any remote work holiday rentals in Sister Bay?
In Sister Bay, Wisconsin, there are numerous remote work holiday rentals available, with around 132 options to choose from. This charming village, located along the Door County shoreline, provides a picturesque backdrop for those looking to combine work and leisure. Many of the properties are equipped with essential amenities for remote work, including Wi-Fi, dedicated desks, and comfortable office spaces, ensuring that you can stay productive during your stay.

The area boasts a range of delightful accommodations, from modern condos to quaint cottages, often featuring additional comforts such as fully equipped kitchens and inviting living spaces. Some rentals may also offer outdoor areas where you can unwind after a day of work, allowing for a superb balance between productivity and relaxation. 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 often include kitchens, which allow guests to prepare their own meals, as well as patios for enjoying the outdoors. Most rentals come equipped with essential cookware, dishware, and utensils, alongside conveniences like microwaves and refrigerators.
When is the best time to visit Sister Bay for a holiday rental?
The best time to book a holiday rental in Sister Bay is during the peak season from June to August. This vibrant period draws visitors eager to experience the stunning natural beauty of Door County, with its numerous outdoor activities, charming shops, and local festivals. July stands out as the most popular month, when the warm temperatures, typically ranging from the mid-teens to low 20s Celsius, create an inclusive setting for both relaxation and adventure.

During these summer months, you can indulge in kayaking, hiking, and exploring the picturesque shoreline of Lake Michigan. The scenic views and vibrant sunsets are superb for outdoor dining or simply enjoying a leisurely stroll along the waterfront.

For those looking for a more budget-friendly option, consider visiting in November. This quieter month offers a unique opportunity to appreciate the serene beauty of Sister Bay without the summer crowds. While temperatures dip, the crisp air can be refreshing, and you might find cosy accommodations at a great value.
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, Wisconsin, visitors can enjoy a variety of charming attractions that highlight the area's natural beauty and local culture. The picturesque waterfront offers stunning views of the bay, superb for relaxing strolls or enjoying a picnic. Nearby, the Sister Bay Marina is a hub for boating and fishing activities, attracting both locals and tourists alike.

For those interested in exploring the outdoors, the scenic Door County Coastal Byway provides breathtaking views and access to several parks and nature trails. The nearby Sister Bay Park features a sandy beach, picnic areas, and playgrounds, making it an ideal spot for families.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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