Condo vacation rentals in Ashland County

4.91 out of 5 average rating, 144 reviews

Bayfield Studio | Lake Superior View

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

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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, 182 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.

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5 out of 5 average rating, 25 reviews

Condo in Ironwood

UTV/ATV Lodge w/Games + Firepit: Schnickelfritz #4

Schnickelfritz #4 is a fun, one-of-a-kind lodge retreat steps away from Big Powderhorn Mountain, putting year-round adventure right at your doorstep! With easy access to the main chalet, ski-lifts, and nearby trail systems, enjoy skiing in winter and convenient access to hiking, biking trails, and ATV riding in the warmer months. After a day of action, kick back in the shared basement lounge with a Sauna, Pinball, Foosball, Pool Table, and more! Free washer and dryer included. Pets $50 per stay

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4.96 out of 5 average rating, 112 reviews

Condo in Wakefield

Cute & Cozy 1B/1B Condo w/ Jetted Tub!

My clean, cozy, quiet, and Completely remodeled condo is located at Indianhead/Snowriver Resort. It's a brief walk to the Sky Bar/Jack's Cafe on site for food, drink, and the best views from the top of the ski hill in the Upper Peninsula. My condo is the perfect place for your romantic getaway, family trip, after hiking/camping refresh, ski vacation, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!

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4.96 out of 5 average rating, 126 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

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4.95 out of 5 average rating, 58 reviews

An aerial view captures the winter landscape surrounding the condo units, blanketed in fresh snow. The buildings are set back from a frozen pond, with evergreen trees visible in the background. A ski lift stands nearby, indicating access to the slopes.

Condo in Wakefield

Ski In & Ski Out

Hike, bike, ski, snowshoe, sightsee…we can go on! This stunning ski-in/ski-out condo offers unparalleled access to Jackson Creek Summit part of the Snowriver Mountain Resort. Situated on the top of the hill, this peaceful residence ensures you can hit the slopes as soon as you step out the back patio door. The perfect retreat for access to many area destinations including Porcupine Mtns, waterfalls, ski hills (Jackson Creek, Black River Basin, Big Powderhorn, Whitecap) and much more!

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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.

4.93 out of 5 average rating, 44 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.

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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, 389 reviews

One Minute Walk to Lake Superior. Brookside #11

Amazing location! Strong Wifi updated in May 2026. This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. 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. The pool an restraunt opens July 1st. 5 minutes to Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

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4.88 out of 5 average rating, 163 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.

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4.91 out of 5 average rating, 128 reviews

Condo in Ironwood

Wildflower Loft | 1BR King | Downtown + Near Trail

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. Wildflower Loft features local Upper Peninsula decor, a king bed, and sleeper sofas, perfect for a comfortable stay in the heart of it all.

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Superhost

The open living area is furnished with a comfortable plaid sofa and a wooden coffee table. A television is mounted on the wall across from the seating. A dining table with chairs is positioned nearby, and a large window allows natural light to fill the room.

Condo in Bessemer

4.77 out of 5 average rating, 52 reviews

Ski Lodge Condo across from Big Powderhorn Resort

Powdermill Resort economy Condo across from the Big Powderhorn Mountain Ski Resort and just minutes from Black River Harbor, Copper Peak, Blackjack and Indianhead Big Snow Resorts. This is a top floor two-story condo overlooking a beautiful forested area above the Powdermill Creek. The condo was totally remodeled in 2020 with new kitchen, bathroom, carpet, fixtures, and more.

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