Port Wing vacation rentals

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Top-rated vacation rentals in Port Wing

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Port Wing

4.9 out of 5 average rating, 197 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.

Guest favorite

Cabin in Hayward

4.94 out of 5 average rating, 246 reviews

The Timberjack

Although it's a rustic homage to the lumberjacks and jills of yesteryear, this cabin includes many of the comforts we now enjoy including a queen bed, kitchenette with fridge, hot water, AC/heat, a Keurig coffeemaker, smart TV and charcoal grill. The Timberjack is surrounded by trees right on Lake Hayward and close to downtown Hayward. Launch your canoe just steps from the cabin, walk into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the ideal location!

Guest favorite

Cabin in Herbster

4.97 out of 5 average rating, 105 reviews

Cedar Ridge | Hand-Crafted Cabin w/Lake Views

This newly built cabin will take your breath away. You’ll find the perfect blend of Northwoods rustic charm and creature comforts in this 3 bdrm cabin nestled in the woods overlooking Lake Superior’s Bark Bay. You’ll fall in love with all the care & attention its owners have put into every detail. From the stunning cedar beams that provide the backdrop to the incredible lake views to the hand-crafted interior woodwork and the beautiful kitchen, you will see how unique and special this cabin is.

Guest favorite

Cottage in Herbster

4.98 out of 5 average rating, 248 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.

Guest favorite

Shipping container in South Range

4.99 out of 5 average rating, 104 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Storage containers converted into a Nordic sauna and living space. Set in the woods half a mile from the sandy south shore of LAKE SUPERIOR. Our two-person occupancy and minimal design are curated to re-focus and re-fresh its inhabitants. Located on 80 acres of private land, you will fall in love with the peace and quiet. Whether you’re looking for a romantic couples getaway, spa weekend, or workspace as a digital nomad, Sölveig Stay was designed to spark creativity and relaxation.

Guest favorite

Home in Poplar

4.97 out of 5 average rating, 315 reviews

Cozy Cabin with Trails, River, Fireplace, Private!

Timber Trails Cabin is a small country home ideal for a relaxing getaway! It is centrally located in the heart of Northern Wisconsin’s recreational opportunities. Enjoy our trails on 60 acres or take a short drive to local lakes, the Brule River, or Lake Superior. Within walking distance is the Poplar Golf Course and Bar/Grill. At the end of the day, you can relax around a fire under the starry sky. If it is chilly outside enjoy the fireplace and some games, books, or movies!

Guest favorite

Loft in Iron River

5 out of 5 average rating, 118 reviews

Boho Bunkhouse

Take it easy at this unique and tranquil getaway. Set in the north woods, 3 miles north of Iron River on the ATV/Snowmobile trails. *15 minutes from Lake Superior. *50 minutes from Bayfield *50 minutes from Duluth. Relax & read a book, hit the trails, or head to the lake. The South Shore area is filled with activities. Kayaking, fishing, hiking, swimming, waterfalls, ATV-UTV-Dirtbike riding and much more. Visit our local breweries, wineries, museums and nature center.

Guest favorite

Cabin in Herbster

4.93 out of 5 average rating, 166 reviews

SOUTH SHORE A-FRAME//Steps from Lake Superior

A peaceful, feel good place. 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

Cabin in Herbster

5 out of 5 average rating, 126 reviews

Superior Sunsets @ The West Slope (Steam Shower)

Our 3 bedroom, 2 bath home is located 1 mile out of Cornucopia and 20 miles from Bayfield. Nestled in a lush forest on a sandstone cliff overlooking Lake Superior, this home features wifi, STEAM SHOWER , a fully equipped kitchen and cozy gas fireplace . Deck with grill and stunning sunset views. Large entertainment room w/ 65" Smart T.V. , POOL TABLE & DART BOARD. Outdoor firepit and picnic table. WE PRACTICE ENHANCED SANITIZING MEASURES DURING COLD IN FLU SEASON.

Guest favorite

Cottage in Herbster

4.99 out of 5 average rating, 175 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!

Superhost

Cabin in Herbster

4.95 out of 5 average rating, 173 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.

Guest favorite

Guest suite in Duluth

4.99 out of 5 average rating, 496 reviews

Private Blue Pine Getaway

Conveniently situated 20 miles north of Duluth, 15 minutes south of Two Harbors and inside 10 acres of woods, this place offers a getaway from today’s hectic fast paced living. This is a perfect place to relax and take in the sounds, smells and beauty of nature. You will hear birds and crickets, breathe in fresh air and often spot deer.