Condo holiday rentals in Madeline Island

4.82 out of 5 average rating, 85 reviews

Downtown Bayfield 2 BR Condo fireplace sleeps 6

Perfect for a long weekend get-away or extended stay in Bayfield. Cozy two bedroom condo located right downtown. Boatworks is the only condo in town with an elevator. Walk to all the famous Bayfield restaurants and Saloons. (Most only a 2-3 blocks from condo) . Lake Superior across the street. Explore the City Dock, 2 Marinas, ferry to Madeline Island, local golf coarse, fish charters, sail boating, Apostle Islands National Lake Shore (22 islands). 5 star Orchards surround Bayfield.A must tour.

4.91 out of 5 average rating, 126 reviews

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

4.98 out of 5 average rating, 150 reviews

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.

4.8 out of 5 average rating, 293 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen air matress. Full kitchen, balcony, AC, CableTV, Strong WiFi, fire pit wood povided. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Bikes provided. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. $40 pet fee per stay. 🙂 No smoking allowed.

4.95 out of 5 average rating, 100 reviews

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

4.97 out of 5 average rating, 30 reviews

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.

5 out of 5 average rating, 5 reviews

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.

5 out of 5 average rating, 16 reviews

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 8, 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!

4.88 out of 5 average rating, 134 reviews

Condo in Ashland

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.

4.88 out of 5 average rating, 152 reviews

The Fireside at Silver Creek B&B w/ SAUNA

The Fireside at Silver Creek Bed & Breakfast is a comfortable condo outside of beautiful Two Harbors. It is one of three private units at the home, nested on 11 explorable acres. Perfect for outdoor enthusiasts and those seeking relaxation. We are located 5 miles off lake Superior near some of the best outdoor activities MN has to offer: Gooseberry Falls (13min), Split Rock (20min) and Stewart river (3mi) for trout fishing.

5 out of 5 average rating, 34 reviews

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!