Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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Guest favorite

The Griffin riverboat is docked under a colorful rainbow, with its name prominently displayed on the side. Surrounded by lush greenery, the scene is illuminated by the warm light of sunset reflecting off the water's surface.

Houseboat in Superior

4.96 out of 5 average rating, 138 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 spacious yard is featured, with four red Adirondack chairs arranged around a circular fire pit, creating a cozy gathering space. The green bungalow is visible in the background, surrounded by trees and open grass, with a deck and patio umbrella situated on one side.

Home in Superior

4.99 out of 5 average rating, 143 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 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, 783 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

The exterior of the bunkhouse features a vibrant, multicolored metal siding with shades of red, blue, and brown. A simple wooden deck leads to the front door, which is flanked by a small window. A single chair is positioned on the deck, inviting relaxation.

Farm stay in Wrenshall

4.96 out of 5 average rating, 155 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

Superhost

A two-story building is presented, featuring a combination of dark green roofing and beige siding. Windows are positioned on each level, offering natural light. The front entry doors are framed by minimal landscaping, with an expanse of green grass and a gravel pathway leading to the building.

Home in Duluth

4.92 out of 5 average rating, 199 reviews

Beautiful home or 2 apartments Duluth/Spirit Mtn

This unique building offers an enormous amount of outside space and privacy nestled in a wooded area. The huge yard gives plenty of outdoor space for kids and adults alike to enjoy the view. Optimal for 1-7 people, for a variety of uses from business travel, to the perfect family vacation with instant access to all of Duluth's attractions and events. Parties of 2+ have access to both floors, open concept. Parties of 1-2 the bottom studio provides a full apartment! We are next to Spirit Mt!

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

4.94 out of 5 average rating, 178 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!

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, 169 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

This charming cottage is framed by lush greenery and colorful flowering plants. A private porch features two chairs, inviting relaxation. A neatly maintained pathway leads through a wooden fence, completing the serene outdoor setting against the backdrop of trees.

Cottage in Brule

4.98 out of 5 average rating, 268 reviews

The Cottage: No cleaning fees! Access to trails!

We are an event center but do not have events or weddings during your stay. This cozy one-bedroom cottage is set against the tree line. In the morning, enjoy coffee on the private porch, go snowshoeing, hiking, fishing, or canoeing in and around Brule River State Forest in the afternoon, and watch a few movies in the evening. Are you traveling with a group? Check out our other listing, The Farmhouse at Brule River Barn, a four-bedroom, two-bath home that can accommodate 11 guests.

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

4.96 out of 5 average rating, 355 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 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.

Apartment in Superior

4.9 out of 5 average rating, 174 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

A modern living space is presented, featuring an inviting round dining table set with dishes and a floral centerpiece. A light-colored sofa is positioned nearby, accompanied by a black coffee table. Art pieces adorn the walls, while natural light brightens the room.

Apartment in Superior

4.89 out of 5 average rating, 279 reviews

Superior Bay Boutique Motel Suite #11

This 1 bedroom suite has a contemporary decor, detailed amenities and an excellent location. The unit is spacious and has an open floor plan, featuring a living room furnished with a sofa, love seat, tables, built in wall cabinets, TV/cable and high top dining table and 2 stools. The unit has a full kitchen that is stocked for extended stays. The large bedroom features a king bed and 2 closets, one is a walk in. The bedroom also has TV/cable and an iron/iron board.

Guest favorite

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 home in Lake Nebagamon

4.96 out of 5 average rating, 428 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!