Port Wing vacation rentals

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Top-rated vacation rentals in Port Wing

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Guest favorite

Home in Port Wing

4.9 out of 5 average rating, 177 reviews

Kinney Valley Farm

This rustic, but modernized farmhouse is on 110 acres of woods and apple orchards. Snow is great now! Cross country ski trails are " skier-groomed" on our property. Multiple areas for groomed skiing are within 30-45 minute drives. Located just 3 miles from the south shore of Lake Superior, and 30 minutes from the Apostle Island Sea Caves, spectacular now with winter ice sculptures, Kinney Valley Farm is a cozy place to stay, while exploring the pastoral winter beauty of Northern Wisconsin.

May 9 – 16

€ 115 per night

Guest favorite

Guest suite in Brule

4.97 out of 5 average rating, 135 reviews

The Bee's Balm

You'll find us tucked in the quiet woods of northern WI near the Brule River. We're remote enough to experience star-filled skies & fireflies, but not far from many premier attractions. Your space is a self-contained apartment on the lower level of our 2.5 story home. It features a private entry, queen-sized bed, kitchenette, lower level private deck, access our beautiful grounds & more! We're a family of artists who love to travel & to introduce others to our beautiful part of the world.

Sep 3 – 10

€ 106 per night

Guest favorite

Cabin in Iron River

4.95 out of 5 average rating, 123 reviews

Log Cabin and Spider Lake

Step back in time in an authentic seventy year old hand hewn log cabin located on a northern Wisconsin lake with no public access. The cabin has all modern amenities. Rental includes two kayaks, a canoe, a 14 foot fishing boat, and two bicycles. The cabin sits of 1.5 wooded acres with 300 ft. of lake frontage. There is no WIFI in the cabin. WIFI is available 3 miles away at the Iron River library 24/7. The cabin has cell service. Nightly rate includes state and local occupancy tax

Dec 5 – 12

€ 170 per night

Guest favorite

Cottage in Herbster

4.98 out of 5 average rating, 210 reviews

Lake Superior's Cranberry River Cottage- The Raven

Enjoy beautiful Lake Superior in the clean cozy modern cottage located in the quaint little town of Herbster where the Cranberry River enters It's just a short couple blocks to the beach and playground. Enjoy the beautiful sunsets, swimming, boating, kayaking, biking, fishing, hunting, and skiing with ATV and snowmobile trails nearby. Explore the Chequamegon Nat'l Forest or venture to Bayfield, home of the Apple Fest, or visit the Apostle Islands Nat'l Lakeshore to see the sea/ice caves.

Dec 11 – 18

€ 122 per night

Guest favorite

Guest suite in Cornucopia

4.98 out of 5 average rating, 129 reviews

Come love the south shore of Lake Superior

The Cornucopia Sweet Retreat is a unique open concept living space above Corny Coffee in Cornucopia, Wisconsin. We are just steps from Lake Superior and the Cornucopia beach shops. Lost Creek Adventures is across the street and offers guided kayak tours to the sea caves, and Ehlers grocery store has wonderful deli sandwiches and salads. We are located 20 minutes from Bayfield, Wisconsin and the ferry to Madeline Island. The Cornucopia Sweet Retreat is a no smoking / no pet space.

Oct 2 – 9

€ 166 per night

Guest favorite

Cabin in Herbster

4.94 out of 5 average rating, 139 reviews

SOUTH SHORE A-FRAME//Steps from Lake Superior

A peaceful, feel good place. Newly renovated rustic modern Aframe off Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach, breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.

Guest favorite

Cottage in Herbster

4.99 out of 5 average rating, 138 reviews

Applegate Cottage - South Shore of Lake Superior

Applegate cottage is an adorable cottage located just a short walk from the beautiful beach in Herbster, Wisconsin on the Lake Superior Scenic Byway. Whether you like hiking, biking, kayaking, skiing or just relaxing, there’s something nearby for everyone. Bayfield County has orchards, wineries, the Apostle Islands, sea caves, boutique shopping, waterfalls, great restaurants and so much more! Best of all…the sunsets! And, every season brings it’s own beauty!

Nov 4 – 11

€ 156 per night

Guest favorite

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 350 reviews

Berrywood Acres Cabin

Berrywood Acres is located on the eastern shores of Lake Nebagamon. We are known for beautiful sunsets with quiet surroundings and located minutes from the famous Brule River, great hiking trails nearby and a 35 minute drive from Duluth/Superior or a bit further east to the Bayfield/Ashland area. The cabin is simple with all you need for a little RnR. Come relax on the porch and enjoy the view. We look forward to welcoming you to Berrywood Acres Cabin!

Sep 9 – 16

€ 140 per night

Guest favorite

Home in Brule

4.84 out of 5 average rating, 132 reviews

Cabin in the Pines

We are just an hour from the Apostle Islands, Bayfield, Hayward, Ashland, Wi or Duluth, Mn. As you head north to Lake Superior surrounded by the silence of the forest, you can relax , away from the bustle of everyday life. The famous Bois Brule River is a short walk down the hill. Our cabin is very quiet. We are on 3 acres. Our place is a cabin. Not a house. We aren't fancy but comfortable. Get set for a beautiful peaceful time in the pines.

Oct 19 – 26

€ 122 per night

Superhost

Cabin in Herbster

4.96 out of 5 average rating, 157 reviews

Casa Cranberry - A Year-Round Cabin

Welcome to Casa Cranberry! Settle into the peace and quiet near the south shore of Lake Superior in the northern Wisconsin woods. Have a campfire next to the Cranberry River, and let the sounds of the river lull you to sleep at night. Fish in this class A trout stream, play on the Herbster and Cornucopia Beaches, hike in the woods, or kayak on Lake Superior. Casa Cranberry is a perfect jumping-off point to explore Bayfield and the Apostle Islands.

Mar 7 – 14

€ 193 per night

Guest favorite

Tiny home in Lake Nebagamon

4.98 out of 5 average rating, 313 reviews

Deer Haven - Cozy Northwoods Tiny House

Deer Haven is a tiny house (192 sq feet) located in my backyard, overlooking acres of woodland. The space is small and simple. Get to the queen bed in the sleeping loft by climbing the ladder. Bathroom has a toilet and stock tank shower. The kitchen has basic amenities - fridge, microwave, hot plate, griddle, dishes, etc. Best spot in the house is on the couch, where you can see the fireplace and the gorgeous woods out the patio door.

Oct 3 – 10

€ 123 per night

Superhost

Yurt in Bayfield

4.96 out of 5 average rating, 287 reviews

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

Sep 14 – 21

€ 89 per night