Holiday rentals in Lakeside

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.

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

Sunflower Home w/ Game Room, Hot Tub +Pet Friendly

Enjoy a relaxing vacation at this beautiful, spacious three-story home! The home is equipped with a full size game room which includes PAC-MAN Arcade Game, a ping pong table, foosball, and a basketball hoop! There is also an outside private hot tub for use! (more details below). The home has a fenced in yard for your 4 legged family members to run around in. Located 4 minutes from the University of Wisconsin-Superior, 5 minutes from Barkers Island, and 10 minutes from Duluth! PET FRIENDLY!

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.

Aurora Black | The Brix | Pool in Canal Park!

Aurora Black by The Brix: A cozy 2-bedroom, 2-bathroom retreat in historic Canal Park with stunning views of the William A. Irvin ship. Perfect for families and adults alike, it features bunk beds for kids, modern amenities, games, an indoor pool, hot tub, on-site micro-brewery, and cocktail bar. Steps from the Aerial Lift Bridge, restaurants, and shops. The Brix Passport unlocks exclusive discounts at 25+ local businesses—eateries, breweries, stores—via a user-friendly digital pass.

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.

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!

Private Blue Pine Getaway

Welcome to our unique two-story rustic-modern cabin, a one-of-a-kind retreat that blends industrial charm with warm, natural touches. Conveniently situated 20 miles north of Duluth and 10 miles south of Two Harbors. Nestled in a peaceful setting with a partially fenced yard for privacy, this space offers the perfect mix of seclusion, comfort, and style. Whether you're here for an outdoor adventure or a quiet getaway, our home has everything you need to relax and unwind.

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!

Stay Lincoln Park 4 | Craft District Condo

Nestled in the heart of the Lincoln Park Craft District,The Stay Lincoln Park building offers a cozy 2-bedroom, 2-bathroom retreat. This inviting getaway is just steps away from a variety of local gems, including breweries like Bent Paddle and The Tap Exchange, cider spots like Duluth Cider, and dining favorites such as OMC Smokehouse and Love Creamery. Shopping enthusiasts will also enjoy being close to unique stores like Frost River Trading Company.

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.

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.