Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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Guest favorite

A red Adirondack chair is positioned on the deck, overlooking the calm water at sunset. The reflection of the colorful sky is visible on the water's surface. Wooden docks and boats can be seen in the background, adding to the serene setting.

Houseboat in Superior

4.97 out of 5 average rating, 117 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

Two kayaks are stored on wooden racks attached to a green exterior wall. The kayaks display a bright blue color, with one kayak resting above the other, both securely held in place by the rack.

Home in Superior

4.98 out of 5 average rating, 121 reviews

Cozy Bungalow for Adventurers: Nature in the City

Take it easy at this unique and tranquil getaway. Nestled back in a quiet Superior neighborhood, this quaint, two bedroom bungalow with a large secluded yard, deck, and fire pit is between 5-15 minute drive away from pretty much anywhere you’d like to be: Lake Superior, waterfalls, biking trails, hiking trails, ATV trails, cross country & down-hill skiing, breweries, live music events, restaurants, shopping, Canal Park, Barkers Island, Wisconsin Point, Bikes, kayaks, lawn games. ID #ALED-CRFKS8

Top guest favorite

A quaint bathroom features floral wallpaper and vintage decor elements. A compact toilet is situated adjacent to a wooden shelf holding neatly arranged towels and toiletries. A small mirror with an ornate frame adds charm, while a cozy rug completes the inviting atmosphere.

Guest suite in Superior

4.97 out of 5 average rating, 755 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 landscaped garden area features a stone fire pit surrounded by metal chairs. Pathways meander through vibrant flower beds, leading towards a serene pond. Wooden benches are positioned nearby, under the dappled shade of trees, inviting relaxation in the natural surroundings.

Guest suite in Brule

4.97 out of 5 average rating, 167 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 group of brown hens is seen foraging in a grassy field, with a backdrop of trees. Some hens are close to the camera, showcasing their vibrant red combs and wattles. A henhouse structure is visible in the distance, adding context to the farm setting.

Farm stay in Wrenshall

4.97 out of 5 average rating, 127 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

4.95 out of 5 average rating, 129 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

Two modern outdoor chairs face a circular fire pit on a stone patio, situated in front of a sleek black shipping container. Large windows reflect the surrounding greenery, and a standing heater is positioned nearby.

Shipping container in South Range

4.98 out of 5 average rating, 147 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

A hammock is suspended between two trees, offering a view of a gentle stream bordered by smooth stones. Lush green grass and foliage surround the scene, enhancing the natural setting that invites relaxation and connection with nature.

Home in Poplar

4.96 out of 5 average rating, 341 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 well-lit bathroom features a modern vanity with a round mirror above it. A towel hangs from a ring next to the sink. The room is connected to a hallway that leads to a dining area, visible through an archway.

Apartment in Superior

4.9 out of 5 average rating, 154 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

The exterior of a rustic cabin is displayed, featuring a wooden façade, a blue metal roof, and two green doors. A porch with two wooden rocking chairs invites relaxation, with vibrant flowers in planters nearby and greenery framing the scene.

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 412 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!

Guest favorite

Home in Brule

4.84 out of 5 average rating, 169 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.

Guest favorite

A cozy outdoor fire pit is surrounded by several wooden Adirondack chairs, creating an inviting gathering space. A cabin with a green roof is visible in the background, nestled among trees and open grass. The sun casts a warm glow over the scene.

Cabin in Brule

4.93 out of 5 average rating, 148 reviews

Brule River Cabin -Boxcar Hole

****New gazebo on the River*** Brule River Cabin is a two-bedroom plus a loft located right on the famous Brule River. It’s also located on the Box Car Hole, an excellent fishing spot. Canoes are available from Brule River Cabin Rental. The cabin is good for couples, solo adventurers, families (with kids), and groups of up to 8 people. The cabin features high-speed internet, a washer and dryer, and central heat and AC.

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Popular amenities for Lakeside vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Lakeside

Guest favorite

An aerial view captures a snow-covered landscape adjacent to Lake Superior, showcasing a line of trees and road leading to the shore. The water appears calm with gentle waves, and various properties are visible along the shoreline, highlighting the natural beauty of the area.

Cottage in North Shore

4.89 out of 5 average rating, 128 reviews

Cozy Cottages with a Superior View Cottage #6

AlexandraRating, 5 stars3 weeks ago

Absolute gem of a place! Perfect location with an incredible view of Lake Superior. The hosts were very responsive and accommodating of our short notice stay. I wish we could have stayed forever. Would be thrilled to stay at North Shore Cottages again in the future!

Guest favorite

A sleeping area featuring a lofted bed with a floral-patterned quilt. Wooden beams and rustic charm enhance the cozy ambiance. Soft lighting from overhead fixtures creates a warm glow, while a round window allows natural light to filter in.

Cabin in Brule

4.79 out of 5 average rating, 53 reviews

Trout Camp

MichelleRating, 5 stars2 days ago

This cabin was a perfect location between visiting Pattison/Amicon State Parks and the Bayfield area. The cabin was clean and extremely cozy. And it was pet friendly to be able to bring our lab with exploring all this area has to offer!

A bathroom features a bathtub with a shower curtain, surrounded by wood paneling and stone tiles. A small wooden bench is positioned near the tub, and a window above allows natural light to enter the space.

Apartment in Port Wing

4.86 out of 5 average rating, 7 reviews

Lake Wind Subterranean Suite

RileyRating, 5 stars2 weeks ago

The location was perfect for our plans. They left us a small bag of fresh ground coffee, next to the coffee pot, & it was absolutely amazing! We only needed a clean bed and private entrance, & that's exactly what we got! We thought the bed was extremely comfortable, & the sheets were clean and smelled fabulous! It is located in a basement, so I did notice a couple cobwebs in the corners, but overall it's very clean! Also, the shower is not made for tall people, my fiance is 6'4" and had to squat to take a shower. Small complaints, compared to how wonderful everything else was. Shower essentials were provided, including towels. It was quit, comfortable, & private. I would definitely recommend. 10/10.

Guest favorite

A cozy seating area features a yellow couch adorned with decorative pillows. Large windows provide a view of the surrounding trees and natural landscape, allowing ample light to fill the room. Modern sconces are mounted on the walls, adding subtle illumination.

Guesthouse in Lake Nebagamon

4.9 out of 5 average rating, 42 reviews

Cozy & Charming Guesthouse

MaryRating, 5 stars1 week ago

Great place to spend the week and could have stayed longer.....

Superhost

An open living space features light-colored walls, a comfortable seating area with two armchairs, and a dark couch. A wooden coffee table sits on a patterned area rug. The dining area includes a round table with grey chairs, while a kitchen space is visible in the background.

Home in South Superior

4.87 out of 5 average rating, 61 reviews

The Itty-Bitty Inn

TerryRating, 5 stars1 week ago

Was very charming and well put together. It felt very comfortable and was what we needed.

Top guest favorite

A bright living room is presented with a comfortable seating area facing a gas fireplace beneath a mounted television. Potted plants and artwork add color to the neutral walls. Natural light filters through the window, highlighting the textured carpet and cozy atmosphere.

Guest suite in Duluth

5 out of 5 average rating, 51 reviews

Quiet comfy apt near trails

EileenRating, 5 stars3 days ago

Jenny’s place was beautiful. Her rental is meticulous, in a pretty, peaceful neighborhood, with easy access to 61 which made our ride up to Grand Marais even more special. She responded to us immediately when we had an issue with the door key and was most pleasant.

Superhost