Condo vacation rentals in Bayfield County

A wooden dining table with four chairs is positioned in the center, accompanied by a stationary menu holder. A comfortable couch is visible in the background, facing a light-filled sliding door leading to a balcony. Warm lighting from lamps adds a cozy ambiance.

4.83 out of 5 average rating, 86 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.

A modern studio condo interior is presented, featuring a spacious bed with a quilted coverlet. A gas fireplace offers warmth, while large windows frame panoramic lake views. A light-toned armchair and decorative shelves enhance the cozy ambiance, with a bright door leading to an outdoor space.

4.91 out of 5 average rating, 129 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

Top guest favorite

A bright living room is characterized by light wooden flooring and natural light. Two white sofas are positioned around a wooden coffee table, with a decorative lamp on one end. A large television is placed in front of a wooden cabinet, and a doorway leads to the rest of the condo.

4.98 out of 5 average rating, 157 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.

A living area features a navy blue sofa paired with a rustic wooden coffee table. A television is mounted on the wall, and light streams in through a sliding glass door leading to a balcony. A dining area with a small table is also visible.

4.8 out of 5 average rating, 295 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-August. 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.

A studio space features a spacious bed and a queen sofa sleeper, accented by neutral-colored walls. Natural light enters through a nearby window, illuminating the cozy sitting area with its black couch. A small dining table and kitchenette are seen in the background.

4.8 out of 5 average rating, 374 reviews

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.

The spacious living room features a cozy arrangement of seating, including a large sofa and a pair of armchairs. A coffee table sits centrally on a decorative area rug. Natural light filters through the windows, illuminating the neutral-colored walls and wooden accents.

4.95 out of 5 average rating, 103 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

A spacious outdoor deck overlooks the harbor, featuring a large dining table with matching chairs and a blue umbrella for shade. The serene lake view is framed by colorful autumn foliage, contributing to the inviting outdoor space.

4.94 out of 5 average rating, 33 reviews

Bayfield on the Lake - Waterfront Condo (#303)

Unit #303 at Bayfield on the Lake is the premier place to stay in Bayfield while exploring the town, Madeline Island, and the Apostle Islands. Located directly on the harbor, there is no better view in town. Walking distance to everything including shops, the Madeline Island Ferry Line, beaches, playgrounds, dining, and more. With 4 bedrooms, a game room that includes a foosball table, a kitchen with brand new appliances, this condo is perfect for large groups looking to get away.

4.91 out of 5 average rating, 54 reviews

Modern Beach Front Condo with Lake Views

Enjoy stunning Lake Superior views in this chic and modern 1 bedroom condo that is literally steps from the beach! This unit offers everything you could want in a temporary home during your visit to Bayfield. The unit features a newly renovated kitchen & bathroom, a comfortable queen-size mattress in the bedroom, and comfy living room furniture from which to enjoy the incredible lake views. You'll also be able to enjoy a private balcony overlooking the lake & beach, just steps away.

The living room features a comfortable couch and a coffee table, with a TV positioned on a wooden stand. Artful fish decorations are mounted on the wall. Natural light enters through a nearby window, creating a warm ambiance in the space.

4.79 out of 5 average rating, 39 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.

4.89 out of 5 average rating, 141 reviews

A bright living area features a comfortable gray sofa complemented by a round area rug. A wooden coffee table sits in front of a TV mounted on the wall. Natural light streams through a large bay window, enhancing the welcoming atmosphere.

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.

4.67 out of 5 average rating, 51 reviews

A wooden deck extends from the cabin, furnished with a picnic table and adirondack chairs. A small grill is positioned nearby, and the area features a stone fire pit surrounded by grass and trees. Large glass doors provide indoor access to the cabin.

Condo in Iron River

Deer Trail Resort Lakeside 3 on Lake Delta

At Deer Trail #3 relish the simple pleasures of outdoor living—picnicking at the deck’s large picnic table, grilling with breathtaking views, or exploring local attractions and events. Whether you’re seeking high-energy adventures or a relaxing escape into nature, Deer Trail Resort caters to a variety of interests, making it an ideal getaway for every season. The Cabin features 2 Bedrooms a full bath. Pet Fees not included.

A clear blue sky is highlighted by the sun, casting a bright light over a marina filled with various sailboats. Tall masts reach upward, creating a striking vertical composition against the horizon.