Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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Superhost
Loft in Spirit Valley
4.92 out of 5 average rating, 532 reviews

Experience Duluth Arts in the BB Makers Loft

The BB Makers Loft vacation rental is the newly renovated studio apartment above the BB Event Gallery. Charming, unique, and locally furnished, visitors of the BB Makers Loft experience Duluth’s local and vibrant arts community first hand. Unlike any other hotel or vacation rental, the BB visitors can stay, sleep, shop, and support local artisans right from the comfort of the loft. The home is located in the Spirit Valley neighborhood in West Duluth. Canal Park and Downtown is a 10 min drive.

Top guest favorite
Home in Superior
4.93 out of 5 average rating, 114 reviews

Sunflower Home w/ Game Room, Hot Tub +Pet Friendly

Enjoy a relaxing vacation at this beautiful, spacious three-story home! The home is equipped with a full size game room which includes PAC-MAN Arcade Game, a ping pong table, foosball, and a basketball hoop! There is also an outside private hot tub for use! (more details below). The home has a fenced in yard for your 4 legged family members to run around in. Located 4 minutes from the University of Wisconsin-Superior, 5 minutes from Barkers Island, and 10 minutes from Duluth! PET FRIENDLY!

Top guest favorite
Guest suite in Superior
4.97 out of 5 average rating, 799 reviews

Penrose House An English escape by Lake Superior

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.

Top guest favorite
A private deck features a glass table surrounded by two chairs with cushions, complemented by vibrant planters. In the background, a lush garden blooms with various flowers and greenery, creating an inviting outdoor retreat.
Guest suite in Brule
4.97 out of 5 average rating, 199 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.

Guest favorite
A rustic wooden cabin is surrounded by vibrant autumn foliage. Large windows allow natural light to fill the interior, while a sloped roof adds character. A wooden deck leads up to the entrance, enhancing the cabin's connection to the landscape.
Cabin in South Range
4.85 out of 5 average rating, 154 reviews

Cabin in the Northwoods

Come and enjoy all the Northwoods of Wisconsin has to offer at our beautiful, secluded cabin on our private lake, Long Lake. Enjoy all the amenities we have ,such as, hot tub, canoes, fire pit, and more! Here you will have immediate access to ATV and snowmobile routes, fishing on a private lake, and trails for hiking or hunting. Also conveniently located approximately 15 minutes out side of Superior Wisconsin where you will have access to any needs or amenities along with more sites to see!

Top guest favorite
The exterior of the storage container unit is showcased in a serene setting, featuring large windows and a sleek black facade. The surrounding area is landscaped with grass and bordered by a stone path, under a sky painted with soft hues of sunset.
Shipping container in South Range
4.99 out of 5 average rating, 200 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.

Top guest favorite
A cozy fireplace room features a comfortable sofa adorned with a checked blanket. Natural light streams in through multiple windows, illuminating the wood-paneled walls. A decorative rug with nature motifs adds warmth to the space, with a fireplace providing a focal point.
Home in Poplar
4.97 out of 5 average rating, 380 reviews

Cozy Cabin with Fireplace! River, Trails, 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
Apartment in Superior
4.91 out of 5 average rating, 195 reviews

Executive Apt. 1BR 1BA, w/Q Bed

A charming, historical accommodation has prepared a place for you. This special place is close to everything, making it easy to plan your visit. One bedroom and one bath with immaculate, delightful decor. This home away from home is only blocks away from downtown Superior restaurants, vibrant nightlife, quaint coffee shops, and sweet, unique boutiques. Either that, or you might want to order in, put your feet up, relax, and watch a film. We look forward to your visit!

Top guest favorite
A charming cabin with wooden siding is surrounded by colorful autumn foliage. The exterior features large green windows and a decorative quilt pattern on the front wall, indicating a welcoming atmosphere. A slight lawn leads towards the porch, offering a view of the nearby lakeside.
Tiny home in Lake Nebagamon
4.96 out of 5 average rating, 443 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!

Top guest favorite
A cozy interior features a sleeping loft accessed by a ladder, with a spacious couch in the foreground. The kitchenette showcases modern appliances and reclaimed wood accents, while natural light streams through large windows adorned with light-colored curtains.
Tiny home in Lake Nebagamon
4.98 out of 5 average rating, 390 reviews

Cozy Fireplace in a 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.

Top guest favorite
The entrance to the cottage is framed by lush greenery and flowers, inviting guests inside. A pathway made of stones leads to a bright red door, flanked by two relaxed seating areas. A wooden fence surrounds the property, enhancing the private atmosphere.
Cottage in Brule
4.98 out of 5 average rating, 289 reviews

The Cottage: No cleaning fees! Access to trails!

This charming one-bedroom cottage sits peacefully by the tree line, inviting you to start your mornings with coffee on the private porch. Spend afternoons exploring snowshoeing, hiking, fishing, or canoeing in Brule River State Forest. In the evenings, unwind with movies in your cozy retreat. For larger groups, consider renting The Farmhouse at Brule River Barn, a spacious four-bedroom, two-bath home sleeping 11.

Guest favorite
An efficiency apartment features a spacious bed with a patterned quilt. A full kitchen with essential appliances and a dining area for four is also visible. Neutral-colored walls enhance the room's overall brightness, while natural light enters through the window with blinds.
Apartment in Chester Park
4.9 out of 5 average rating, 284 reviews

Private studio apartment near UMD

New and comfortable efficiency apartment with full kitchen and utensils for home cooking, full bath, table, chairs, dresser, Roku TV, and queen bed. Off street parking, laundry usage, and wifi all included. Fully private with lock and key. Great location just ten minutes walking to UMD, on bus line, and only a few minutes drive from downtown/Canal Park or the mall area.

Popular amenities for Lakeside vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Douglas County
  5. Lakeside