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

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, 758 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 donkey grazes on lush grass in a serene wooded area. Surrounding dandelions dot the grassy landscape, while the foliage provides a natural backdrop. A low wooden fence, comprised of branches, is positioned in the foreground, enhancing the tranquil rural setting.

Guest suite in Brule

4.97 out of 5 average rating, 169 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, 129 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

An A-frame bedroom features a spacious bed dressed in a colorful blanket. Natural wood paneling and beams create a warm ambiance, while modern lighting fixtures are mounted on the walls. A large window allows natural light to enter, providing views of the surrounding woods.

Cabin in Hayward

4.99 out of 5 average rating, 104 reviews

Seeley Oaks A-Frame | Quiet, 40 Acres, Near Trails

This is a cabin-in-the-woods experience! The Seeley Oaks A-Frame is our slice of the peaceful Northwoods experience. It's on 40 private, tranquil acres (no neighbors!) with great access to all the Hayward-Cable area has to offer. It's small - intended for two adults, with the option of 2 addtl kids. It's a total of 700 sq ft, with a queen bed in the loft, in-floor heat, full kitchen, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

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 Superior

4.95 out of 5 average rating, 133 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

A serene outdoor space features a well-maintained lawn surrounded by trees, leading to a sleek storage container structure. A small patio area is visible, furnished with seating options, inviting moments of relaxation in nature.

Shipping container in South Range

4.98 out of 5 average rating, 148 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 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

4.97 out of 5 average rating, 343 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, 157 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, 414 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, 172 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.

Superhost

A well-appointed bedroom features a spacious bed adorned with crisp white linens and decorative pillows. Natural light fills the room from nearby windows. A door leading to another area is visible, enhancing the room's accessibility and flow.

Apartment in Superior

4.83 out of 5 average rating, 166 reviews

Barker's Urban Oasis

Welcome to our charming 2-bedroom apartment nestled in the historic East End neighborhood of Superior, Wisconsin. With its prime location, this cozy retreat offers a perfect balance of comfort, convenience, and local charm for an unforgettable stay. Barker's Urban Oasis is the upstairs unit in a duplex. This house was built in the early 20th century, during the Industrial Revolution, which contributed to Superior's early growth and prosperity.

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Popular amenities for Lakeside vacation rentals

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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, 129 reviews

Cozy Cottages with a Superior View Cottage #6

AlexandraRating, 5 stars1 month 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!

Top guest favorite

The modern cabin is set against a backdrop of trees, illuminated by warm string lights that create an inviting atmosphere. A gravel pathway leads to the entrance, with the dark exterior contrasting beautifully against the dusk sky filled with soft pink and purple hues.

Cabin in Esko

5 out of 5 average rating, 22 reviews

Cabin & Treehouse by Jay Cooke State Park / Duluth

HeidiRating, 5 stars4 days ago

Cory’s place was 10/10. Beautifully decorated and furnished, a kitchen with anything you could need for making it a home away from home, comfortable beds, clean. I could go on and on. It really is just the perfect little peaceful oasis. The treehouse is adorable and it’s surrounded by nature: bird sounds in the morning, beautiful trees and other wildlife too! The fully screened in porch was so appreciated as well; we were able to enjoy evenings with cozy lighting and no bugs! Truly one of the best air BNB experiences we’ve had!

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 stars1 week 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!

Superhost

A black rooster with a bright red comb stands prominently in the foreground, showcasing its vivid features. In the background, a white duck is visible, partially blurred, creating a natural farmyard atmosphere.

Home in South Range

4.76 out of 5 average rating, 34 reviews

Trains & Chickens! Sleeps 5/Dog-Friendly

LukeRating, 5 stars1 month ago

Hidden Pond Junction was our home during an unexpected event for our family. Tom and Cindy went out of their way to make us comfortable. We had the most enjoyable stay we could have dreamed of. The home was set up for us to live in and the kitchen was fantastic! Many cookies were baked, birthdays had and relaxing like we have never experienced. Our family would highly recommend this place to everyone looking for a great getaway place. We will go back for sure!! We will never forget our time at Hidden Pond Junction. -The Olsons

Top guest favorite

A spacious living area showcases natural wood beams and a stone fireplace, adding warmth to the environment. Comfortable leather sofas are positioned around a wooden coffee table, creating an inviting space for gatherings. A well-lit kitchen is visible in the background.

Cabin in Two Harbors

4.98 out of 5 average rating, 56 reviews

Luxury Home with Lakeside Sauna

ShannonRating, 5 stars6 days ago

We loved staying at this cabin! It was extremely thoughtful with all of the amenities, I loved the products, the towels and bedding were pristine- the kitchen was very accommodating with pots, pans, and dishes. The decor was funky , cool and eclectic. The home felt very clean. I didn’t see any dust or hairs. All around great place to stay with our family, you can’t beat the view, spacious cabin and lots of beds. Will be back.

Top guest favorite

Two comfortable black chairs are arranged around a central fire pit, set on a bed of wood chips. A backdrop of tall evergreen trees frames the scenic view of the lake in the distance, creating a serene outdoor space.

Barn in Duluth

5 out of 5 average rating, 51 reviews

The Bergen Lake Barndo

LisaRating, 5 stars3 days ago

We wanted private, peaceful and clean and that’s what we got. I would definitely stay there again.

A campfire is constructed with wooden logs on a sandy beach, creating a warm glow as the flames dance. The calm water of Lake Superior reflects the vibrant colors of the sunset, transitioning from soft orange to blue hues in the sky.

Cabin in Poplar

5 out of 5 average rating, 5 reviews

Lk Superior Cabin with hot tub & private beach

StephenRating, 5 stars9 months ago

The photos don’t do this location justice! The accommodations were top notch, and Jeanne makes you feel like family! Worth every penny! Will be back again to show more friends and family this amazing place!

Guest favorite

An open interior showcases wooden beams and a cozy layout. A textured rug covers the floor, with a chair and table positioned next to a window. Stairs lead to a loft area, while a hanging plant adds a touch of greenery to the space.

Farm stay in Carlton

4.98 out of 5 average rating, 54 reviews

The Cabin @ Ru-Ridge (The perfect place to relax)

HugoRating, 5 stars1 day ago

Buckle your bunnies because this Cabin… What’s in store is such a fun experience getting to stay offline. The out house reminded me alot of the one in Shrek! From building a fire, to spending time with the horses, and sleeping in such tranquil surroundings at night. THE STAY WAS GREAT! ps. bring a battery pack for your electronics because there are no outlets in the cabin. 🤠

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Vacation rentals in Lakeside

Top-rated vacation rentals in Lakeside

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Popular amenities for Lakeside vacation rentals

Other great vacation rentals in Lakeside

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