Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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Top guest favourite
The modern cabin features a unique timber frame design and large glass windows, offering expansive views of the surrounding landscape. The exterior is complemented by natural stone and landscaped areas with vibrant fall colors, adding to the serene environment.
Cabin in Two Harbors
4.97 out of 5 average rating, 149 reviews

Architect-designed, net zero home w/ stunning view

Great for a couple's getaway or family excursion, perfectly located on the North Shore with a spectacular view of Lake Superior. Features stunning timber frame modern design, luxurious master bed and bath, spacious deck, and porch with fireplace. There's nothing else like it on the North Shore. It is perfectly located 20 minutes from Duluth and 5 minutes from Two Harbors, 5 from a boat launch. Our cabin is certified as Net Zero Ready through the DOE and was designed and built by Timberlyne.

Top guest favourite
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, 794 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.

Guest favourite
A spacious cabin with a distinctive wooden exterior features large triangular windows that provide ample natural light. A deck overlooks the yard, furnished with several red chairs and a grill. Lush green trees surround the property, enhancing its natural setting.
Cabin in South Range
4.85 out of 5 average rating, 147 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 favourite
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
4.94 out of 5 average rating, 217 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 favourite
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, 188 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 favourite
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, 373 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!

Top guest favourite
The living area features a modern television on a dark media console. Two armchairs and a sectional sofa surround a central ottoman on a large area rug. Natural light enters through a nearby window, illuminating the warm wood flooring.
Home in Denfeld
4.99 out of 5 average rating, 308 reviews

Entertainment & Outdoor Activities - Hub

Stay in the heart of Duluth—your ideal base for both vacations and business trips. Just minutes from Lincoln Park’s Craft District, Downtown, and Canal Parks local breweries, cider houses. Adventure awaits with quick access to Spirit Mountain, the Munger State Trail, hiking, mountain biking, paddling, boating, fishing, birdwatching, and more. Experience the perfect blend of comfort, convenience, and outdoor fun in one of Duluth’s most exciting neighborhoods.

Top guest favourite
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 homes 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 favourite
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 homes in Lake Nebagamon
4.98 out of 5 average rating, 386 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 favourite
A spacious living area features a dark leather sofa adorned with patterned cushions, positioned next to a wooden coffee table. Natural light fills the room through multiple windows, accentuating the minimalist decor and hardwood flooring.
Apartment in Superior
4.87 out of 5 average rating, 441 reviews

Where You Wanna BnB

This cute updated 2 bedroom apartment has everything you need! Whether your'e on a short business trip or taking a lengthy vacation to enjoy the beautiful Twin Ports, my apartment provides the perfect location. Only blocks away from restaurants and bars on the famous Tower Avenue and less than 10 minutes from Canal Park in Duluth. Pattison Park and Amnicon Falls are also only a short drive away!

Top guest favourite
A firepit surrounded by four wooden chairs is set on a gravel area, offering panoramic views of Lake Superior and the surrounding landscape. Lush greenery frames the scene under a clear blue sky, creating a peaceful outdoor space for relaxation.
Cottage in Duluth
4.98 out of 5 average rating, 567 reviews

Cottage with Lake Superior & North Shore views

Tucked away on 1.5 acres in the middle of Duluth, this one-bedroom cottage has breath-taking panoramic views of Lake Superior, the Aerial Lift bridge and the St. Louis River. With the large property and surrounding trees, the home feels secluded but has wonderful access to hiking and biking trails, parks, beaches and all that downtown Duluth and Canal Park have to offer. License PL23-023

Top guest favourite
A modern kitchen presents light green cabinetry paired with a large island featuring bar stools. Pendant lights hang above, and stainless steel appliances are visible. The open layout invites natural light, with a cozy seating area and a welcoming entrance to the left.
Home in Superior
4.94 out of 5 average rating, 218 reviews

The Treasure House- Near Duluth & Pet Friendly!

Come enjoy a stay at a newly renovated home. A perfect fit for both couples & families! 5 minutes from Barkers Island & less than 15 minutes from Duluth & Canal Park. You will find this a welcoming, cozy & relaxing home. The home is Pet Friendly. BE SURE to include your pet(s) in your reservation since there is a $75 nonrefundable pet fee.

Popular amenities for Lakeside vacation rentals

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