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Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
A cozy bedroom features a spacious bed adorned with soft linens, flanked by two bright windows with natural light filtering through. A modern wood wall accent is centered above the bed, while a love seat is positioned nearby, completing the inviting space.
Loft in Spirit Valley
4.93 out of 5 average rating, 527 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
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, 796 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 favorite
A light-filled living area is presented with large windows and neutral-toned walls. A soft gray sofa is paired with two minimalist armchairs, while a glass coffee table displays a few decorative items. Soft lighting from modern floor lamps creates a welcoming ambiance.
Apartment in Superior
4.93 out of 5 average rating, 393 reviews

Historic Modern 10 min across bridge to Duluth

Enjoy this freshly restored historic building in your private 2 bedroom apartment. Bask in the morning sun with a cup of coffee on your private balcony. The open layout with 11 foot ceilings, large kitchen and kitchen island, white quartz countertops , the newly finished wood floors, and the incredibly comfortable beds will all welcome you to your home away. In-Unit Laundry, WIFI, 4K TV with cable and Netflix/Amazon, Wine Cooler, Elevator access and off street parking. Licence # TBES-BEJSS8

Guest favorite
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, 150 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!

Guest favorite
A well-appointed bedroom features a spacious bed with soft linens and decorative pillows. A nightstand with a lamp is positioned beside the bed. An oval mirror and a wooden dresser add character, while natural light filters through the window, highlighted by white blinds.
Apartment in Superior
4.77 out of 5 average rating, 132 reviews

Pattison's Peaceful Retreat

Welcome to our charming 2-bedroom apartment nestled in the heart of Superior's historic East End neighborhood. With its blend of modern comfort and vintage charm, this delightful retreat offers you an inviting space to relax and unwind while enjoying the beauty and history of the area. Pattison's Peaceful Retreat is the downstairs 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.

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, 224 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, 193 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, 377 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 favorite
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, 313 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.

Guest favorite
A lofted sleeping area features a large bed with a dark green coverlet, complemented by decorative pillows. Exposed wooden beams and a ceiling fan add to the rustic charm. A comfortable seating area with two armchairs is visible across the room, illuminated by natural light from windows.
Loft in Two Harbors
4.95 out of 5 average rating, 166 reviews

The Loft @ Silver Creek B&B

The Loft at Silver Creek B&B is a cozy lofted condo unit outside of beautiful Two Harbors. It is one of three private units at the home, nested on 11 explorable acres. Perfect for outdoor enthusiasts and those seeking relaxation. Be sure to enjoy our Sauna! We are located 5 miles off lake Superior near some of the best outdoor activities MN has to offer: Gooseberry Falls (13min), Split Rock (20min) and Stewart river (3mi) for trout fishing.

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, 388 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
Cottage in Brule
4.98 out of 5 average rating, 285 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.

Popular amenities for Lakeside vacation rentals

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