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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 41 Vacation Homes in Port Wing with updated reviews, rates, and availability.

McNeil's on the Brule
Property grounds

McNeil's on the Brule

9.8 out of 10, Exceptional, (137)
"This quaint house nestled on the banks of the beautiful Brule River made for a great late fall getaway. If you want to disappear in the woods of Northern Wisconsin for a spell, this is a fantastic property to do so."
McNeil's on the Brule
Timber Frame House overlooking Lake Superior, 20 miles from downtown Duluth
Exterior

Timber Frame House overlooking Lake Superior, 20 miles from downtown Duluth

10.0 out of 10, Exceptional, (103)
"This was the perfect location for a large group to relax and welcome in 2025. We enjoyed hiking to the shore, games, and enough space for all of us to gather around the fire. The kitchen was adequate to feed everyone and there were seats enough for all to enjoy meals together. The large TV downstairs was great for a few wanting to watch a football game."
Timber Frame House overlooking Lake Superior, 20 miles from downtown Duluth
Lake Superior Panoramic Waterfront Views; Summer 2025 Now Booking!
Sunrise view from the living room over Lake Superior!

Lake Superior Panoramic Waterfront Views; Summer 2025 Now Booking!

9.8 out of 10, Exceptional, (53)
"We had a wonderful time with our whole family over Thanksgiving. The house was spacious with plenty of room to both spend time together and spread out to get a little space. The host was really responsive and helpful. The house did feel a little bit like a maze to start with but was okay once you got use to it."
Lake Superior Panoramic Waterfront Views; Summer 2025 Now Booking!
Two bedroom cottage near beautiful Herbster beach.
Exterior

Two bedroom cottage near beautiful Herbster beach.

10.0 out of 10, Exceptional, (82)
"Outstanding property. Picturesque. Great outdoor area. Neat and tidy. Comfortable furniture and bedding. Kitchen is well stocked for cooking. Easy to find. Two minutes to Lake Superior. "
Two bedroom cottage near beautiful Herbster beach.
Lake Superior Views Log Home
The deck level accesses the main floor of the cabin.

Lake Superior Views Log Home

10.0 out of 10, Exceptional, (130)
"This cabin was a nice cozy cabin with enough sleeping room for the six adults we had plus we had one more bed for a single. It was located where we needed it to go further north or to go into Duluth. It was great. We came back one day and there were just four deer roaming around the property and the other day when I woke up there was one peeking in the window. Would definitely stay here again and would definitely recommend. If I was gonna stay at Christmas, I would bring Christmas decorations....
Lake Superior Views Log Home
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Exterior

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

9.4 out of 10, Exceptional, (24)
"It was a very quaint and cozy place to stay that was very relaxing and enjoyable. "
The price is AED 481
AED 1,321 total
includes taxes & fees
26 Jan - 27 Jan
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!
Welcome to South Shore Chalet!

Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!

10.0 out of 10, Exceptional, (19)
"Well maintained property with several amenities. We had a great time with our family & dog. "
Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!
The Landing on Lake Nebagamon - Includes Pontoon!
Exterior

The Landing on Lake Nebagamon - Includes Pontoon!

10.0 out of 10, Exceptional, (72)
"We stayed at the landing for our daughter's wedding in nearby Poplar. The lake house was perfect for our group with multiple families. The two kitchens and refrigerators made it easy to prepare food for our group and the wedding party. We enjoyed a dip in the chilly October lake and then warming in the sauna. Host was very responsive and flexible on checkout and checking times. Would definition stay againagain!refrigergreat for preparing lunch for weekend"
The Landing on Lake Nebagamon - Includes Pontoon!
Balsam House in Washburn, Wisconsin
Front entrance

Balsam House in Washburn, Wisconsin

2.0 star property
9.6 out of 10, Exceptional, (7)
"Very much enjoyed our stay. Clean and comfortable, with outstanding responsiveness and support from the facility manager. Would stay again!"
Balsam House in Washburn, Wisconsin
Rustic Lodge near Lake Superior
Lodge Exterior - Front door, sidewalk

Rustic Lodge near Lake Superior

10.0 out of 10, Exceptional, (2)
"We had a wonderful time staying at the Amnicon lodge! Everything exceeded our expectations, and it was a great place to relax and enjoy the nature. The one thing I would say is that the bathroom is a shared space with the other cabins on the property. I did not see this listed in the description, but it wasn’t really an issue for us; just good information for future guests!"
The price is AED 2,938
AED 3,526 total
includes taxes & fees
27 Jan - 28 Jan
Rustic Lodge near Lake Superior
Custom Craftsman home. 20 Miles from Downtown Duluth.
Exterior

Custom Craftsman home. 20 Miles from Downtown Duluth.

9.6 out of 10, Exceptional, (70)
"This home has room for everyone to gather for games and meals at a huge table that can seat 12. We loved that. You also can spread out if you want to chill by yourself and take in the views. During our visit it was cold outside so the fireplace was fabulous. PacMan game was so fun. We mostly loved the short walk through the trees down to the beach on Lake Superior. Love this place and really, the drive from Duluth didn't take too long. We noticed some repair is needed to the ping...
Custom Craftsman home. 20 Miles from Downtown Duluth.
Spectacular lake view!
On Pristine North Shore Lake Superior

Spectacular lake view!

9.4 out of 10, Exceptional, (96)
"large home and quiet comfortable bedrooms. Gorgeous view of lake and rocky beach for kids to play on."
Spectacular lake view!
Freshly Remodeled Cabin w/ stunning Lake Views
Entry view into the living room.

Freshly Remodeled Cabin w/ stunning Lake Views

10.0 out of 10, Exceptional, (17)
"Stayed with our family of 6 for an end of summer trip and it was perfect! Perfect location right outside of downtown Two Harbors, perfectly sized to fit our family and perfectly equipped with everything we needed aside from groceries. Would stay here again!"
Freshly Remodeled Cabin w/ stunning Lake Views
Lake Superior Beach Haven with Large LakeHouse
Exterior

Lake Superior Beach Haven with Large LakeHouse

9.6 out of 10, Exceptional, (14)
"We enjoyed our stay at this VRBO. The description of the home and property was accurate. The grounds and home are well cared for. The property and home were clean. It was a quiet setting. Some games were provided if desired. T.V. was available. The beach area was fun to walk along and explore. We enjoyed a campfire in the campfire ring and wood was provided. The hostess was always responsive to our questions in a very helpful and timely manner. "
Lake Superior Beach Haven with Large LakeHouse
Wild Acres Lodge
Exterior

Wild Acres Lodge

9.4 out of 10, Exceptional, (3)
"It was the perfect place to fit all our needs...from age 10 months to 65 years old!"
Wild Acres Lodge
Beachfront and Lakehouse With All of the Comforts!
Beach

Beachfront and Lakehouse With All of the Comforts!

10.0 out of 10, Exceptional, (22)
"Host was very responsive and accomodating before and during our visit. Home was clean and as described. Great yard. Relaxing lake. We hope to return next year for more fall colors. "
Beachfront and Lakehouse With All of the Comforts!
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Exterior

Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

9.4 out of 10, Exceptional, (22)
"This place was perfect for what we needed. The front porch was the highlight of our mornings, drinking coffee in the rocking chairs. It’s within close distance to all the things we were hoping to get to, Bayfield and the apostle islands. It may be due for a bug treatment as there were lots of spiders throughout the house, but other than that this place was awesome!"
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
At the end of Bark Point lies your perfect vacation home!
Welcome to Bark Point Lodge!

At the end of Bark Point lies your perfect vacation home!

9.8 out of 10, Exceptional, (9)
"We had a great time visiting Herbster and staying at this house. The sounds of the waves lapping on the shore with a fire in the fireplace while playing cards at the table was very relaxing. "
At the end of Bark Point lies your perfect vacation home!
Stately home in Washburn
The Baron in summer

Stately home in Washburn

9.8 out of 10, Exceptional, (19)
"We had a wonderful stay at the Stately Home. It was very comfortable with a lot of space for my family (6 adults). It provided everything we wanted, spacious kitchen, dining room, huge living room & comfortable bedrooms. Visiting in the winter we didn’t have the opportunity to enjoy the deck & backyard, but are looking forward to staying at the Stately for our 2025 holiday getaway. "
Stately home in Washburn
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
Welcome to Porcupine Bluff!

This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.

10.0 out of 10, Exceptional, (7)
"We enjoyed our time in Herbster. The cabin was stocked with all the creature comforts, and its location - nestled in the woods along the lakeshore - was outstanding. We enjoyed our morning beverages as we watched the sunrise each morning. Cooking breakfast and lunch in the kitchen was easy with all the provided items. For dinner, we ate at The Cranberry Over Superior - and recommend it! We explored Cornucopia and Port Wing, too. The South Shore had plenty to keep us occupied when we ventured...
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Port Wing

Rustic Personal Retreat Cabin, "Sunset"
Exterior

Rustic Personal Retreat Cabin, "Sunset"

9.8 out of 10, Exceptional, (94)
"Not a single complaint. That little cabin had everything we needed and nothing we didn't. The heated outhouse was AWESOME!!"
The price is AED 217
AED 306 total
includes taxes & fees
26 Jan - 27 Jan
Rustic Personal Retreat Cabin, "Sunset"
Rustic Personal Retreat Cabin, "Sunrise"
Exterior

Rustic Personal Retreat Cabin, "Sunrise"

9.8 out of 10, Exceptional, (113)
"My husband and I loved the little cabin. Like the title is was cozy and peaceful. We had no issues with the bathroom and the real toilets and showers were great. The local trails and lake were easy to get to. My husband and I want to plan another trip to visit again."
The price is AED 253
AED 345 total
includes taxes & fees
26 Jan - 27 Jan
Rustic Personal Retreat Cabin, "Sunrise"
Timber Frame House overlooking Lake Superior, 20 miles from downtown Duluth
Exterior

Timber Frame House overlooking Lake Superior, 20 miles from downtown Duluth

10.0 out of 10, Exceptional, (103)
"This was the perfect location for a large group to relax and welcome in 2025. We enjoyed hiking to the shore, games, and enough space for all of us to gather around the fire. The kitchen was adequate to feed everyone and there were seats enough for all to enjoy meals together. The large TV downstairs was great for a few wanting to watch a football game."
Timber Frame House overlooking Lake Superior, 20 miles from downtown Duluth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.