Condo vacation rentals in Ashland County

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Top-rated condo rentals in Ashland County

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Guest favorite

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.

Condo in Bayfield

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

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.

Condo in Bayfield

4.98 out of 5 average rating, 148 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.

Superhost

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.

Condo 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.

Guest favorite

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

4.97 out of 5 average rating, 30 reviews

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!

Top guest favorite

A spacious balcony area features a table with seating for six, surrounded by comfortable chairs. A serene view of Lake Superior and the marina is visible beyond, with green grass and landscaped garden elements framing the scene.

Condo in Bayfield

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.

Guest favorite

The living area includes two matching recliners facing a spacious bed, with colorful bedding. A kitchen with wooden cabinets and appliances is visible in the background, along with a dining table and a chair. Natural light enters through a window, illuminating the blue carpet.

Condo in Bessemer

4.8 out of 5 average rating, 85 reviews

Room #214 Modern loft condo @ base of Ski Mountain

Two queen beds. Private loft bedroom with vanity sink, dresser and closet. Real kitchen with refrigerator, electric range and oven, microwave, toaster oven, coffee maker, dishes, pots and pans. Matching recliners face the 65 inch TV. Top floor, end unit, second story window looks out at your car in the well lit parking and Big Powderhorn Ski Mountain across the road. One bathroom with tub/shower. Daylight LED track lighting on the high ceilings to brighten your day.

Superhost

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

4.88 out of 5 average rating, 132 reviews

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.

Guest favorite

The image captures a panoramic view of a serene landscape featuring a cluster of brown condos set along a lush green area. A calm body of water reflects the surrounding trees and cloudy sky, with rolling hills visible in the distance, creating a tranquil setting.

Condo in Wakefield

4.97 out of 5 average rating, 196 reviews

Cozy & Clean 2B/2B Condo w/ Jetted Tub!

My clean, cozy, and quiet condo is located at Snow River/Indianhead Resort. It's a brief walk to Jack's Café 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 ski vacation, romantic getaway, family trip, after hiking/camping refresh, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!

Guest favorite

A welcoming entryway features vibrant green double doors. A wooden table with a mirror is positioned nearby, accompanied by a plant for added freshness. The carpeted floor leads towards an open hallway, while a framed picture decorates the wall, adding a personal touch.

Condo in Ironwood

4.91 out of 5 average rating, 110 reviews

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.

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.

Guest favorite

An inviting kitchen area features modern cabinetry and a spacious wooden island with seating for three. A black refrigerator and stove are positioned alongside a sink, with decorative fixtures and a window allowing natural light to brighten the space.

Condo in Wakefield

4.97 out of 5 average rating, 90 reviews

Sun Dance Apartments unit 1

Full condo with one queen bed in the bedroom and pull out couch in the living area. Can sleep 4 comfortably. You also have access to a full kitchen. Enjoy Snow River Ski Resort and snowmobile trails just yards away from the property in the winter or hiking the porcupine mountains and other outdoor activities in the summer! We kindly ask for no pets at this time.

Guest favorite

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.

Condo in Bayfield

4.93 out of 5 average rating, 57 reviews

Cozy Boatworks #202 Condo Pet friendly. Elevator.

Bayfield Condo Rental - Boatworks #202 is a cozy 1 bedroom 1 bath condo 2nd floor property with elevator. 690 sq ft. Private off-street parking. Located across the street from Apostle Island Marina. Fully equipped kitchen, living room with fireplace, bedroom with queen size bed, full bath. Central air conditioning. Outdoor patio.