Condo vacation rentals in Madeline Island

Beachfront Condo -Stunning Views & Convenience All

This charming condo has everything you could want in your Bayfield getaway and more! This second floor (top floor) studio condo unit features panoramic lake views, a crisp & modern interior, new gas fireplace, fully-equipped kitchen, and even a private deck overlooking the lake (perfect for dining al fresco or enjoying a sunset cocktail). There's even a sandy beach for swimming literally steps from the condo! The condo is located an easy walk to Bayfield's myriad charming shops & restaurants as

Captain's Cabin

Centrally located in the heart of downtown Bayfield--this charming, ground-level condo is just steps away from restaurants, coffee shops, and a block from City Dock and the Lake. The 830 sq.ft condo sleeps 4. A spacious bedroom holds a king bed while the living room has queen sleeper sofa. Located in the historic George Crawford House on one of Bayfield's classic brick lined streets, private parking is provided at the rear of the building with a short walk to the best of everything in Bayfield.

The Fireside at Silver Creek B&B w/ SAUNA

The Fireside at Silver Creek, is a comfortable & inviting unit just outside the charming town of Two Harbors. One of three private units on our 11-acre property. 5 miles from Lake Superior, you’ll be close to some of Minnesota’s top outdoor attractions, including: Gooseberry Falls (13 min), Split Rock Lighthouse (20 min), Gitchi-Gami State Trail. Whether you're hiking, sightseeing, biking, or simply relaxing by the fire, The Fireside offers the ideal base for your North Shore adventure.

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV and fire pit wood provided. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

Lakeview Condo: Downtown Bayfield, Beach, Deck

Experience the charm of Bayfield in our spacious top-floor condo with breathtaking views of Lake Superior.  Perfectly situated, it's an ideal spot for sunrise enthusiasts & offers quick access to downtown. Enjoy the comfort of modern living in a serene lakeside setting. Walk to shops, restaurants, & the island ferry, or relax on the deck overlooking the lake. • 3 bedrooms + loft, sleeps 8 • 2.5 bath, fully stocked kitchen • Deck w/ dining table • Smart TV w/ streaming • Washer/dryer

Beachside Bliss | Airy Vibes and Island Views

Bliss out at Beachside Bliss! You’ll love the bright and airy feel in this fully renovated condo in the center of Bayfield! Beachside Bliss has plenty of space for your adventures: two bedrooms and two baths, anchored by a big common area, plus a roomy balcony with an incredible sunrise view of Lake Superior and Madeline Island. This is a view you could get used to--and with space to spread out, plus creature comforts galore, Beachside Bliss is a place you can really settle into.

Northshore Lake Superior views King Suite | pools

Escape to the serene beauty of Lake Superior with our Lake View King Suite. Nestled in a prime location, this cozy 1-bedroom, 1-bathroom retreat offers breathtaking lake views from bed bedroom and balcony, a luxurious Jacuzzi, and a warm fireplace for those chilly evenings. Enjoy modern comforts, including a fully stocked kitchen. Perfect for couples seeking a romantic getaway or a family looking for adventure, peace, and tranquility. Experience the charm of MN NorthShore with us.

Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed

This comfortable, well-decorated 3-bedroom ground-level condo sleeps 6. It has been recently upgraded with a new couch, table, and fast Wi AC. The location is amazing—a true hidden gem. It is next to the great waters of Lake Superior, surrounded by tall trees, and has a perfect bike trail to the city of Bayfield. The condo is a one-minute walk to the marina/restaurant. The city of Bayfield is 2.3 mi from Brookside condos. You can hike or bike the Brownstone Trail along the lake.

Two Harbors Lakefront 2BR | Pool • Hot Tub • EV

Wake up to sunrises over Lake Superior and fall asleep to waves outside your window in this 4th-floor condo. With 2BR/2BA, 3 fireplaces, 1 jetted tub, and space for 6, it’s perfect for families, friends, or your pup. Enjoy a balcony with epic views plus resort perks — pool, sauna, and indoor/outdoor spa — all minutes from Gooseberry Falls and Split Rock Lighthouse. Dive into lakeside living and create unforgettable North Shore memories at this exceptional luxury retreat!

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

Penthouse w/pool & hot tub

Retreat to the tranquility of Minnesota’s breathtaking North Shore. Located in the charming town of Two Harbors, this three bedroom lakefront penthouse is situated in a private bay. The condo features expansive windows showcasing stunning views of Lake Superior. Amenities include an indoor pool, indoor/outdoor hot tub, fitness area, sauna, and beachfront bonfire. Come unwind in the serenity of nature!

Downtown "Green Room" at Villages on Aurora

Escape to Village on Aurora, your downtown Ironwood retreat! Steps from the City Square and Historical Ironwood Theater, with Lake Superior's beaches and waterfalls a short drive away. Enjoy trails for hiking, biking, and more, plus EV chargers nearby. This condo features local Upper Peninsula decor, a king bed, and sleeper sofas, perfect for a comfortable stay in the heart of it all.