Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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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 3 – 10

G$23,860 GYD per night

Guest favorite

Guest suite in Superior

4.97 out of 5 average rating, 661 reviews

Penrose House Suite for 4 (Lic. No. TBES-AVZSAR)

Penrose house is an original Edwardian home having a private and separate third floor suite. Guest access and entry to the suite is through two high security doors leading to a back stairway used exclusively by guests. Safe off-street parking is available at the rear of the property for guest use only. Our property is located in one of the most sought after streets in the heart of the Central Park area of Superior, Wisconsin. We are centrally located for tourist destinations in the Northland.

Mar 4 – 11

G$18,123 GYD 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.

Apr 7 – 14

G$20,319 GYD per night

Guest favorite

Cottage in Herbster

4.98 out of 5 average rating, 211 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.

Jan 15 – 22

G$25,351 GYD per night

Guest favorite

Home in Poplar

4.97 out of 5 average rating, 274 reviews

Timber Trails Cabin, near Middle River!

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!

Nov 15 – 22

G$27,952 GYD per night

Guest favorite

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 352 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!

Oct 2 – 9

G$28,695 GYD per night

Guest favorite

Cottage in Lake Nebagamon

5.0 out of 5 average rating, 124 reviews

Guest House at the Lake

GUESTS 6 MONTHS & UP MUST BE FULLY VACCINATED & BOOSTED TO RESERVE. Be our guest in this lovely guest house on Lake Minnesuing! Curl up with a good book near the gas fireplace, or play the old fashioned board games provided. In 10 minutes you can be cross country skiing/snow shoeing on the Afterhours Ski Trails, with some trails overlooking the famous Brule River. Superior & Duluth along the shores of the world's largest fresh water lake is 30 minutes away.

Oct 19 – 26

G$32,485 GYD per night

Guest favorite

Home in Brule

4.84 out of 5 average rating, 133 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.

Dec 6 – 13

G$23,023 GYD per night

Superhost

Tiny home in South Range

4.9 out of 5 average rating, 228 reviews

Cozy Cabin near Lake Superior

The perfect place to get away from the distractions of life and enjoy the great outdoors. Tucked away in the woods of the Northland is this primitive, cozy, little cabin; or as we like to call it, "The Shabin". Come enjoy some fishing, kayaking, swimming, hiking, or a little R&R. Whether you cook indoors, or outdoors over the campfire, is up to you. With only electricity and no running water, you'll get the privilege of touring our outdoor privy.

Jan 14 – 21

G$20,237 GYD per night

Guest favorite

Tiny home in Lake Nebagamon

4.98 out of 5 average rating, 314 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.

May 6 – 13

G$21,509 GYD per night

Guest favorite

Cottage in Brule

4.97 out of 5 average rating, 226 reviews

The Cottage (No cleaning fees! Access toTrails!)

This cozy one-bedroom cottage is set up against the tree line. Enjoy a cup of coffee in the morning on the private porch, go snowshoeing, hiking, fishing, or canoeing in and around Brule River State Forest in the afternoon, then watch a few movies in the evening. Are you traveling with a crowd? Check out our other listing, The Farmhouse at Brule River Barn, a four-bedroom, two-bath home that sleeps 11 guests.

Dec 1 – 8

G$40,574 GYD per night

Guest favorite

Guest suite in Duluth

4.99 out of 5 average rating, 457 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.

Sep 24 – Oct 1

G$29,046 GYD per night