Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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Superhost

The Griffin riverboat is docked under a colorful rainbow, with its name prominently displayed on the side. Surrounded by lush greenery, the scene is illuminated by the warm light of sunset reflecting off the water's surface.

Houseboat in Superior

4.96 out of 5 average rating, 127 reviews

Griffin - The Lake Superior Riverboat

Channel your inner Mark Twain. Read, rock, and relax on the water, at the foot of a retired Northern Pacific Ore dock. The Griffin is a functioning riverboat, driven by paddle wheels, originally modeled after historic Mississippi steamboats. It is located at a mom and pop boat yard, which is quite different from a fancy marina. Work happens here. Metal is welded here. Engines are torn apart and put back together here. Friends become family here. Come and become a part of the Griffin’s story.

Top guest favorite

The modern cabin features a covered deck with ample seating, including bright red Adirondack chairs positioned around a fire pit. Large windows display warm ambient lighting within, while smoke gently rises from the roof, blending with the surrounding woods.

Cabin in Hayward

4.99 out of 5 average rating, 210 reviews

Hayward Haus, Modern Design w/ Classic Experience

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind This cabin was built in 2021 and host is 13 year "superhost" This is a default "no pets" cabin, however exceptions can be made with permission and a fee. Inquire with host. NEMA 15-40R outlet provided for level 2 EV charging. You bring chord and adapter.

Guest favorite

A small, rustic bunk house is showcased, featuring a bright yellow door that stands out against the multicolored metal siding. The structure sits on a wooden deck, with additional features visible in the background, including a greenhouse.

Farm stay in Wrenshall

4.9 out of 5 average rating, 137 reviews

AirB-n-BAWK! The NEST @ Locally Laid Egg Company

Bunk with the Birds -kinda. Sleep in sight of the chickens in this tiny, rustic bunk house. 1/3 of the structure is for the chickens, the other 2/3 is for you - separated by glass. It's a chicken aquarium / PEEP SHOW! The Coop has 3 twins and a full-sized mattress. It is BYO Bedding so come with sheets and/or sleeping bag and pillows. There is a solar charger to charge small devices and run the lamp and fan. The structure is seasonally heated with a Porta Potty near-by, bring a flashlight!

Top guest favorite

The suite features a spacious sleeping area with a queen-size bed adorned with plush bedding and decorative pillows. A comfortable sofa is positioned nearby, accompanied by two armchairs and a small table. Large windows draped with light-colored curtains allow natural light to fill the room.

Guest suite in Superior

4.97 out of 5 average rating, 767 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, 175 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

The exterior of the bunkhouse features a vibrant, multicolored metal siding with shades of red, blue, and brown. A simple wooden deck leads to the front door, which is flanked by a small window. A single chair is positioned on the deck, inviting relaxation.

Farm stay in Wrenshall

4.97 out of 5 average rating, 134 reviews

AirB-n-Bawk! The ROOST @ Locally Laid Egg Company

Rustic, solar bunkhouse - The Roost! Glamping at it's best. Get away from it all in this simple bunkhouse made with recycled materials and wood siding from trees milled on site. Large window, covered deck, outdoor seating and fire ring give you space to commune with nature. With a full and twin mattresses, it is Bring Your Own Bedding so come with sheets, pillows and/or sleeping bag. The structure is heated. Private outhouse near-by, bring a flashlight. Come immerse in this working farm

Top guest favorite

A jetted tub is positioned in a wooden alcove, surrounded by beige tiles. Two towels hang above the tub, and a basket containing toiletries is placed nearby. Soft lighting highlights the tub's gentle curves, creating a relaxing atmosphere.

Apartment in Billings Park

4.96 out of 5 average rating, 144 reviews

Sweet Jacuzzi Suite

Whether you're in the Twin Ports for work or play, our little getaway is the perfect place to unwind. (Let us know if you're bringing the kids! ❤️) Fix up a snack in the kitchenette or relax on the full-size futon. After that, settle into a comfy queen-sized bed after a luxurious soak in the jetted tub! Amble down to nearby, kid-friendly Billings Park, or we're just a short drive away from anything in Superior or Duluth, including shopping, the arts, and our gorgeous Lake Superior!

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

4.98 out of 5 average rating, 152 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

This charming cottage is framed by lush greenery and colorful flowering plants. A private porch features two chairs, inviting relaxation. A neatly maintained pathway leads through a wooden fence, completing the serene outdoor setting against the backdrop of trees.

Cottage in Brule

4.98 out of 5 average rating, 265 reviews

The Cottage: No cleaning fees! Access to trails!

We are an event center but do not have events or weddings during your stay. This cozy one-bedroom cottage is set against the tree line. In the morning, enjoy coffee on the private porch, go snowshoeing, hiking, fishing, or canoeing in and around Brule River State Forest in the afternoon, and watch a few movies in the evening. Are you traveling with a group? Check out our other listing, The Farmhouse at Brule River Barn, a four-bedroom, two-bath home that can accommodate 11 guests.

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

4.96 out of 5 average rating, 348 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

A bedroom features a black metal bed frame with a plush, patterned bedspread and layered pillows. The decorative fireplace is highlighted by soft candlelight, and art pieces add a touch of elegance to the walls. Natural light is softly diffused through nearby fixtures.

Apartment in Superior

4.9 out of 5 average rating, 162 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!

Guest favorite

The exterior of a single-story home is surrounded by mature trees and greenery. A spacious parking area is visible in front, with a white fence providing privacy. Sunlight illuminates the scene, highlighting the charming façade of the house.

Home in Billings Park

4.91 out of 5 average rating, 554 reviews

★ Mid Century Modern!★7 miles to Canal Park★

LICENSE- FACILITY ID #TBES-AW7P46, Approved - Douglas County Health Inspection. This retro house will host your Twin Ports experience. Kitchen amenities provided are cookware, dishes, glasses, silverware, coffee, tea, granola bars. Kitchen appliances include dishwasher, oven, stove, refrigerator, microwave, coffee pot, and toaster. Bathroom linen, toilet paper, shampoo, conditioner, body wash, and hand soap are all provided. Parking off the street - 2 spots.