Port Wing holiday rentals

We found 47 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Port Wing that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Port Wing

Showing deals for:1 Jan - 8 Jan

Room
Exterior
Living area
Private kitchen
Exceptional
(23 reviews)

Woodland Retreat - 10 acres of secluded, wooded trails for you to hide-a-way!

Iron River

8% off
AU$1,413
for 7 nights, 1 cabin
AU$202 per night
includes taxes & fees
Woodland Retreat - 10 acres of secluded, wooded trails for you to hide-a-way!
Exterior
Private kitchen
Interior
Interior
Wonderful
(10 reviews)

Spacious, Secluded Retreat with Rustic Charm

Maple

8% off
AU$5,548
for 7 nights, 1 home
AU$793 per night
includes taxes & fees
Spacious, Secluded Retreat with Rustic Charm
Living area
Interior
Outdoor dining
Modern, well equipped kitchen with gas range.
Exceptional
(120 reviews)

Waterfront guesthouse at cliff's edge of Lake Superior's South Shore, Sky Fire.

Herbster

8% off
AU$2,455
for 7 nights, 1 room
AU$351 per night
includes taxes & fees
Waterfront guesthouse at cliff's edge of Lake Superior's South Shore, Sky Fire.
Living area
Interior
Exterior
Property grounds
Exceptional
(19 reviews)

Lake Superior Beach Haven with Large LakeHouse

Herbster

8% off
AU$5,615
for 7 nights, 1 home
AU$802 per night
includes taxes & fees
Lake Superior Beach Haven with Large LakeHouse
Interior
Outdoor dining
Interior
Exterior
Exceptional
(29 reviews)

Riverview Ridge - Half mile from Trails w/ Trailer Parking

Iron River

8% off
AU$3,254
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Riverview Ridge - Half mile from Trails w/ Trailer Parking
The beautiful Northern Lights sharing the sky with the last full Moon of 2025
Relaxing screened porch
Living area
Coffee station
Exceptional
(59 reviews)

This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!

Herbster

8% off
AU$2,528
for 7 nights, 1 home
AU$361 per night
includes taxes & fees
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
Spacious and open concept dining and kitchen
View of the firepit and lake view.
Living room with walkout to the deck and has great Lake Superior views.
Spacious living room with large TV and walks out to the deck.
Exceptional
(12 reviews)

Private Lake Superior Lakefront Cabin with its own Beach Access!

Herbster

10% off
AU$8,544
for 7 nights, 1 home
AU$1,221 per night
includes taxes & fees
Private Lake Superior Lakefront Cabin with its own Beach Access!
Exterior
Terrace/patio
Living area
Private kitchen
Exceptional
(31 reviews)

Beachfront and Lakehouse With All of the Comforts!

Herbster

8% off
AU$2,528
for 7 nights, 1 home
AU$361 per night
includes taxes & fees
Beachfront and Lakehouse With All of the Comforts!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Port Wing getaway

Learn about the unique charm of Port Wing with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Exploring the natural features in Port Wing

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Port Wing is a great place to get out in nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Meyers Beach (17.8 mi / 28.6 km)
  • Apostle Islands Mainland Sea Caves (19.1 mi / 30.7 km)
  • Lake Delta (20.9 mi / 33.6 km)
  • Bibon Lake (0.6 mi / 1 km)
  • Bark Bay Slough State Natural Area (10.2 mi / 16.4 km)
  • Twin Bear Lake (18.6 mi / 30 km)

Transport to and around Port Wing

Book a flight to Duluth, MN (DLH-Duluth Intl.), the closest airport, located 37.7 mi (60.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Port Wing when booking a holiday rental?
When considering a holiday rental in Port Wing, Wisconsin, the best area to stay would be close to the charming waterfront along Lake Superior. This picturesque setting not only offers stunning views but also provides easy access to various outdoor activities. The nearby scenic trails are superb for hiking and biking, allowing visitors to immerse themselves in the natural beauty of the area.Additionally, the local marina is a delightful spot for those interested in boating or fishing, making it a prime location for water enthusiasts. While the number of properties available in Port Wing may vary, the options tend to be cosy and often come with a rustic charm, ideal for a relaxing getaway.For those keen on exploring, the nearby Apostle Islands National Lakeshore is a must-see, renowned for its breathtaking landscapes and unique sea caves. The local community also hosts various events throughout the year, providing a vibrant setting for visitors.
Where are the best areas for renting a beach house in Port Wing?
For renting a beach house in Port Wing, consider the scenic shores along Lake Superior, particularly in the area near the Port Wing Marina. This location offers holiday rentals that provide direct access to sandy beaches and picturesque lake views. Many properties in this vicinity come equipped with amenities such as outdoor decks, fire pits, and spacious living areas, great for families or groups looking to enjoy a relaxing getaway by the water.Additionally, you might explore the nearby Apostle Islands National Lakeshore, which is renowned for its stunning natural beauty and outdoor activities. Rentals in this region often feature amenities like kayaks for exploring the islands, proximity to hiking trails, and outdoor grills for evening barbecues. The charming community vibe in Port Wing, complete with local shops and eateries, enhances the overall experience for visitors seeking both adventure and tranquillity by the lake.
Where are the best Port Wing ski resort rentals?
For the best ski resort rentals near Port Wing, Wisconsin, consider looking in the nearby area of Ashland, which is approximately a 30-minute drive away and offers access to the beautiful slopes of the nearby ski areas. In Ashland, travellers can find a variety of rental properties, including cosy cabins and modern condos, many of which come equipped with amenities such as full kitchens, fireplaces, and outdoor decks superb for enjoying the natural surroundings.Additionally, the area features properties that cater to families and larger groups, often providing spacious living areas, multiple bedrooms, and access to local recreational activities. Many rentals in Ashland also include features like hot tubs, which are ideal for relaxing after a long day on the slopes.For those seeking a more remote experience, the surrounding Chequamegon National Forest offers opportunities to rent rustic lodges or cabins that provide a true sense of seclusion while still being within driving distance of skiing. These properties typically have amenities such as wood-burning stoves, hiking trails nearby, and sometimes even access to lakes for winter activities.
What is the most popular type of holiday rental accomodation in Port Wing?
In Port Wing, cabins are a popular choice for holiday rentals, with several available throughout the area, often located amidst the natural surroundings. These cabins typically feature rustic charm, including fully equipped kitchens, comfortable living spaces, and outdoor decks or porches for enjoying the serene views of the nearby woods or Lake Superior. Cottages are also quite common, providing a quaint and cosy atmosphere, usually with similar amenities to cabins, superb for couples or small families looking for a peaceful getaway. Additionally, there are several holiday houses that offer more spacious rooms, ideal for larger groups or families, often boasting multiple bedrooms, ample living areas, and outdoor spaces for relaxation.
Are there any family house rentals in Port Wing?
In Port Wing, Wisconsin, there are some family-friendly house rentals available, making it an inviting destination for those travelling with children. Visitors can explore properties located along the shores of Lake Superior, which often come with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for playing or relaxing. Many homes provide amenities such as Wi-Fi, BBQ facilities, and easy access to the beach, ensuring a comfortable stay.The locale's natural beauty is complemented by opportunities for outdoor activities, including hiking and fishing, which are ideal for family bonding. Nearby attractions like the Apostle Islands National Lakeshore offer stunning scenery and adventure, adding to the appeal for families looking to create lasting memories together.
Can I rent a holiday home with a pool or hot tub in Port Wing?
In Port Wing, several holiday homes are available for rent that feature pools and hot tubs. This quaint community on the shores of Lake Superior offers a serene escape with beautiful natural surroundings. Many of the rentals come equipped with private pools or hot tubs, providing a superb spot for relaxation after a day of outdoor activities.Travellers can expect amenities such as spacious living areas, fully equipped kitchens for self-catering, and outdoor spaces ideal for barbecues or enjoying the scenic views. The proximity to the lake also adds to the charm, as guests can indulge in swimming, fishing, or simply taking in the picturesque landscape.
Are there pet-friendly house rentals in Port Wing?
In Port Wing, Wisconsin, there are several pet-friendly house rentals available, making it an attractive option for travellers who wish to bring their furry companions along. The area offers a variety of holiday homes that typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.Many of these rentals are conveniently located near the scenic Chequamegon National Forest, which provides ample opportunities for outdoor activities, including hiking and exploring nature trails that are superb for pet walks. Additionally, the nearby shores of Lake Superior offer beautiful views and spots for picnicking, enhancing the overall experience for pet owners.
Are there any remote work holiday rentals in Port Wing?
In Port Wing, Wisconsin, there are some remote work holiday rentals available, with about 15 options for those looking to combine work and leisure. The area offers a tranquil environment, great for focusing on tasks while enjoying the beauty of nature. Many of these rentals come equipped with amenities tailored for remote work, including dedicated desks, office chairs, and computer monitors, along with reliable Wi-Fi to ensure connectivity.The scenic surroundings of Port Wing provide opportunities for relaxation after work hours, with nearby points of interest such as the shores of Lake Superior and local parks for walking or cycling. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Port Wing?
In Port Wing, popular rental amenities include features that enhance comfort and convenience for visitors. Most holiday rentals come equipped with a kitchen, allowing guests to prepare their own meals. Many properties also provide a deck or patio for enjoying the fresh air and surrounding scenery. A coffee or tea maker is commonly included, ensuring that guests can enjoy their morning brew. Onsite parking is typically available, making it easy for travellers with vehicles. Additionally, many rentals feature a fireplace, adding a warm and inviting atmosphere, especially during cooler months.
When is the best time to visit Port Wing for a holiday rental?
The best time to visit Port Wing for a holiday rental is during the summer months, particularly in July. This period marks the peak season, attracting outdoor enthusiasts eager to enjoy the beautiful shores of Lake Superior and the surrounding natural beauty. With warm temperatures averaging around 20 to 25 degrees Celsius, it's an ideal time for activities like kayaking, hiking, and fishing, making the most of the great outdoors.Visitors flock to Port Wing between June and August for its vibrant setting and numerous local events, including summer festivals and farmers' markets. The picturesque scenery, enhanced by lush greenery and the sparkling waters of the lake, provides a superb backdrop for relaxation and adventure alike.If you're looking for a more budget-friendly option, consider planning your visit in December. While this month is part of the low season, it offers a unique charm, with opportunities for winter sports, peaceful landscapes, and the chance to experience the tranquillity of the area during the quieter months.Ultimately, the best time to book your holiday rental in Port Wing depends on your preferences—whether you seek the lively summer vibes filled with outdoor activities or the serene beauty of winter.
What are the top attractions in Port Wing?
In Port Wing, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The scenic Port Wing Marina is a focal point for those interested in boating, fishing, or simply enjoying the lakeside views. Nearby, the Apostle Islands National Lakeshore offers stunning opportunities for hiking, kayaking, and exploring the picturesque sea caves, making it a top destination for nature enthusiasts.The surrounding Chequamegon National Forest is ideal for hiking and wildlife viewing, with miles of trails that cater to various skill levels. Additionally, the local beaches provide a superb spot for relaxation and swimming during the warmer months. For a taste of local culture, the small-town atmosphere of Port Wing features charming shops and eateries that reflect the spirit of the community.
Are all fees included in the Port Wing holiday homes prices shown on Stayz?
Stayz 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.
Are there any Port Wing holiday homes with parking?
Stayz offers a wide selection of holiday homes in Port Wing 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 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.
Are there any discounts for Port Wing holiday homes?
You can find great discounts on holiday homes in Port Wing on Stayz, 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.
Can I change or cancel my Port Wing holiday home booking on Stayz?
To find Port Wing holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Port Wing?
A long-stay holiday home in Port Wing 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Port Wing holiday home?
Book your Port Wing holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Port Wing?
Prices for holiday homes in Port Wing 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Port Wing to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas