Holiday rentals in Lakeside

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Top-rated holiday rentals in Lakeside

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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, 528 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 favourite
A cozy igloo-style dome is illuminated by warm lights, nestled in a snowy landscape. The structure features a transparent exterior that showcases the interior seating area, surrounded by a thick layer of snow. Nearby, the red exterior of the house provides a contrasting backdrop.
Flat in Woodland
4.98 out of 5 average rating, 133 reviews

NO cleaning fee- Boutique Guest Suite in Duluth

Welcome to your sweet escape at Allendale Orchard in Duluth! A perfect oasis for a couple or solo traveler. Relax on your private deck or in the soaking tub after a day of exploring all that Duluth and the North Shore has to offer. You’ll be close to an abundance of hiking and biking trails, minutes away from quaint coffee shops and award winning restaurants, and can pick your own seasonal fruit right on the property. We’re here to offer all of our guests a personalized and inviting experience!

Guest favourite
A spacious yard is shown, featuring a single-story house with large windows, alongside a red shed. Green trees provide shade, and a vehicle is parked in the gravel driveway. A propane tank is visible near the edge of the property.
Home in Iron River
4.86 out of 5 average rating, 141 reviews

Wade Inn Iron River

The Wade Inn Iron River is a great place to relax and enjoy the quiet beauty of nature and be less than a half mile from town! Very peaceful setting on a quiet wooded lot with lots of shade trees and outdoor table and chairs with a Grill!! Iron River is also a great location, close to National Forests, the World famous Brule river, and Lake Superior all within a fifteen minute drive!! Bayfield and the Apostle Islands are also not too much further, and are great easy day trips to enjoy.

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.
Flat in Billings Park
4.95 out of 5 average rating, 229 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, 197 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 favourite
The cabin is nestled among tall trees, surrounded by lush greenery. A spacious deck extends from the building, accessed by stairs leading down to a stone pathway. A small storage shed is visible to the left of the cabin, complementing the natural setting.
Home in Brule
4.84 out of 5 average rating, 193 reviews

Cabin in the Pines

As you head north to Wisconsin and Lake Superior you are 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. We are just an hour from the Apostle Islands, Bayfield, Hayward, Ashland, Wi or Duluth, Mn. Our cabin is very quiet. We are on 3 wooded 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.

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, 378 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 favourite
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.
Flat in Superior
4.91 out of 5 average rating, 193 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 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 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 favourite
Cottage in Brule
4.98 out of 5 average rating, 286 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.

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, 575 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

Guest favourite
An efficiency apartment features a spacious bed with a patterned quilt. A full kitchen with essential appliances and a dining area for four is also visible. Neutral-colored walls enhance the room's overall brightness, while natural light enters through the window with blinds.
Flat in Chester Park
4.9 out of 5 average rating, 283 reviews

Private studio apartment near UMD

New and comfortable efficiency apartment with full kitchen and utensils for home cooking, full bath, table, chairs, dresser, Roku TV, and queen bed. Off street parking, laundry usage, and wifi all included. Fully private with lock and key. Great location just ten minutes walking to UMD, on bus line, and only a few minutes drive from downtown/Canal Park or the mall area.

Popular amenities for Lakeside holiday rentals

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