Condo vacation rentals in Madeline Island

4.83 out of 5 average rating, 69 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.

4.92 out of 5 average rating, 108 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

Condo in Two Harbors

4.9 out of 5 average rating, 10 reviews

Stunning Lake Superior Condo

Gorgeous condo on Lake Superior shoreline with floor to ceiling windows giving a panoramic view of the lake. Corner unit offers endless views, privacy and the feeling that you are on a ship on the Big Lake! Built by original owner of Superior Shores as his own unit, it has beautiful terra cotta tile floors, vaulted ceilings filled with windows and an impressive floor to ceiling stone fireplace. Make this your perfect spot for entertaining with family and friends and exploring the north shore.

Top guest favorite

4.97 out of 5 average rating, 118 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.

4.95 out of 5 average rating, 91 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

Top guest favorite

Condo in Two Harbors

5 out of 5 average rating, 23 reviews

Waterfront Two Harbors Condo - Pool/Hot Tub (3BR)

Indulge in luxury at this scenic 3-bedroom, 3-bathroom vacation rental. Marvel at breathtaking lake views, enjoy coffee on your private balcony, and relax to the soothing sounds of the water. Ideal for families or groups, this condo offers all the comforts of home, including direct beach access and nearby outdoor adventures. Enjoy the indoor pool, sauna, spa, and cozy up with your pet by the fireplace. Dive into lakeside living and create unforgettable memories at this exceptional retreat!

4.8 out of 5 average rating, 30 reviews

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.

4.81 out of 5 average rating, 277 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ and fire pit wood povided. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. 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.

4.9 out of 5 average rating, 111 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.

4.73 out of 5 average rating, 40 reviews

Modern 1 Bdrm Condo Just Steps from the Lake

This one bedroom condo features everything you could hope for in your home base for your visit to Bayfield: lake views, literally steps to the beach, modern design & decor, fully-outfitted kitchen, and walking distance to everything in Bayfield. This unit features an open plan kitchen-dining-living space that opens up to your own private balcony. You'll find the kitchen well-outfitted should you wish to meal prep during your stay. The bathroom is updated and spacious.

4.84 out of 5 average rating, 115 reviews

Condo in La Pointe

Sheila's Downtown Condo

Walk to absolutely everything! Golf course, marina, ferry, galleries, restaurants, grocery, live music, bike, moped and kayak rentals, museum, beaches. The 1 bdrm condo is located 1.5 blocks from the ferry landing and is right above the Mission Hill coffee shop. The Big Lake is 1/2 block away and can be viewed from the spacious living room windows along with spectacular sunsets. Please note that the condo is not directly on the lake.