Holiday rentals in Lakeside

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Top-rated holiday rentals in Lakeside

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Top guest favourite
A shaded outdoor seating area is presented, featuring two green lounge chairs beside a small circular table. A cozy purple blanket is draped over one chair, and a book lies open on the table. A gentle stream flows nearby, surrounded by lush greenery.
Home in Duluth
4.98 out of 5 average rating, 148 reviews

Peaceful River Escape - A Perfect Getaway Spot

This quaint “Peaceful River Escape” offers respite from the busy life for professionals, couples & families. Nestled on the French River this walk-out basement escape offers the lower half of the house, complete w/views of the river, access to washer/dryer, 2 private bedrooms, a “bonus” sleeping area w/trundle bed (2 single twins), a private bathroom w/shower. We also provide coffee, tea & light snacks in your fridge & kitchenette. If you like special touches & a memorable stay this is for you!

Top guest favourite
Home in Superior
4.99 out of 5 average rating, 176 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 favourite
A tranquil lakeside view highlights a treehouse set among lush greenery, with wooden steps leading to the water. Adirondack chairs are positioned on the grassy bank, alongside a hammock and a weathered boat moored in the calm water.
Home in Park Point
4.98 out of 5 average rating, 142 reviews

Park Point Retreat | Steps from Beach & Canal Park

Welcome to Bayview Cottage, a 5-star, year-round lakeside retreat on Duluth’s iconic Park Point. With Superior Bay in the backyard (private dock) and Lake Superior’s sandy beach just across the street, this cozy yet spacious home offers a rare dual-waterfront experience - perfect for families, couples, and peaceful group getaways. ☀️ SUMMER AT BAYVIEW COTTAGE Guests love summer here because you get two waterfront experiences in one stay: 🏖 Beach across the street for swimming & sun 🚣 Private

Top guest favourite
Cabin in Two Harbors
4.97 out of 5 average rating, 257 reviews

Riverwood Hideaway

This off-grid, solar powered hideaway is on the Knife River just a few miles outside of Two Harbors, Minnesota. The cabin itself is loaded with comfort. A full kitchen, propane refrigerator, solar powered lights and a gas fireplace/furnace offer the conveniences of home. There is an outhouse and firewood for the outdoor firepit. You will have to bring your own water for drinking, but we provide hand and dish washing water at the sink. We have coffee with pour over utensils, dishes, spices.

Top guest favourite
Guest suite in Superior
4.97 out of 5 average rating, 808 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
An aerial view captures the expansive a-frame cabin, showcasing its unique triangular architecture and stone chimney. Surrounded by lush greenery, large decks extend from the structure, providing outdoor space. The soft glow from the windows hints at a warm, inviting interior.
Cabin in Two Harbors
4.99 out of 5 average rating, 233 reviews

Wild Pines Cabin: A-frame w/ Lake Superior views

Enjoy off-grid vibes while being right in the heart of the North Shore. Located 5 minutes from Split Rock Lighthouse, Wild Pines Cabin is a completely renovated 1974 a-frame that sits atop 40 private acres overlooking Lake Superior. During your stay, hike through the property, catch glimpses of wildlife, sip coffee by the fire while taking in the sunrise over the lake, or step out to nearby Gooseberry, Black Beach, or Tettegouche. A beautifully private north woods retreat any time of year!

Guest favourite
A charming log cabin is nestled among tall trees, showcasing a sloped roof and warm wooden exterior. The porch area features a small seating arrangement and decorative stone pathways. A cozy shed is located to the side, surrounded by lush greenery and natural landscaping.
Cabin in Iron River
4.93 out of 5 average rating, 110 reviews

Adorable Northwoods cabin

Come enjoy the North woods in our beautiful little cabin. This cabin is a located in a perfect spot only 2 miles outside of Iron River. Close to tourist areas such as Duluth, Bayfield, Ashland and more. This cabin is the perfect get away. The Brule river is only 8 miles away and can make for the perfect day trip in a kayak or canoe. This cabin comfortably fits 2-4 people! You can enjoy the outdoors at the fire pit or the 3 season porch that gives you the perfect indoor/outdoor feeling!

Top guest favourite
An outdoor deck features a spacious wooden table surrounded by benches, positioned next to a bubbly swim spa. The area is bordered by greenery, providing a sense of privacy and tranquility, while sunlight highlights the textures of the wood and water.
Cabin in South Range
4.97 out of 5 average rating, 108 reviews

Kitchigami Lodge - Lake Superior Beach, Hot Tub!

Secluded on 16 acres, with your own beachfront, enjoy the peace and relaxation of Kitchigami Lodge. Take in dramatic sunsets and soaring eagles, sitting upon the bluff mirador. Share stories by the firepit and play games in the sunroom. BBQ with family and friends and enjoy the bubbly swim spa. Duluth, two state parks and ski resorts are only 30 minutes away. Visit Bayfield & the Apostle islands on a day trip! Relax with friends and family and create memories that last a lifetime!

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, 213 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
4.83 out of 5 average rating, 202 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, 390 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
Yurt in Two Harbors
4.98 out of 5 average rating, 309 reviews

Hot Tub, Sauna, Glamping, Private, Wifi, Kayaks

* All are welcome here * Hot tub, sauna, shower * 4 miles to Superior Hiking Trail, 6 miles to Betty’s Pies, 9 miles to Two Harbors Lighthouse, 9 miles to Gooseberry Falls, 16 miles to Split Rock Lighthouse * Firewood provided * 2 folding kayaks (will fit in any vehicle) * 70 Mpbs Wifi * Pet friendly * 16.5 acres of secluded beauty * Sleeps up to 4 * Electricity * 1 mile of trails on site * Dark skies * Space heaters provided * See more @wildhavenmn on social media

Popular amenities for Lakeside holiday rentals

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