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Condo vacation rentals in Ashland County

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Top-rated condo rentals in Ashland County

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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, 127 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, 153 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 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.

Condo in Bayfield

4.8 out of 5 average rating, 372 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 open-plan living space features a comfortable couch adorned with decorative pillows. A dining area and well-equipped kitchen are visible, along with a spiral staircase leading up to a loft. Natural light brightens the interior through well-placed windows.

Condo in Bayfield

4.89 out of 5 average rating, 19 reviews

Clean Modern Beach Front Condo with Lake Views

Enjoy stunning Lake Superior views in this clean and modern 1 bedroom + loft condo that is literally steps from the beach! The unit features clean and updated spaces throughout, a queen-size mattress in the bedroom, a loft with two additional twin beds, comfy living room furniture from which to enjoy the incredible lake views, and an electric fireplace that adds coziness to the space. You'll also be able to enjoy the private balcony overlooking the lake & beach, which are just steps away.

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!

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, 86 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.

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, 135 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.

Top 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!

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.

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.

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, 91 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.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Ashland County condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

A two-story wooden building is surrounded by snow, featuring multiple balconies with wooden railings. A set of stairs leads to the main entrance, and large windows are visible on both levels, allowing natural light into the interior.

Condo in Bessemer

4.86 out of 5 average rating, 21 reviews

Unit #5 Lumberjack- Trailside Black River Basin

A cozy living area features a soft blue-green sofa with decorative cushions, positioned across from a dark wooden coffee table. Light streams through the windows, complemented by sheer curtains. A patterned rug covers the floor, adding texture to the space.

Condo in Ironwood Township

5 out of 5 average rating, 5 reviews

Summertime Bliss at Powderhorn Mountain

A warm living area features a leather sofa and a cozy armchair arranged around a stone fireplace. A flat-screen TV is mounted above the fireplace. Natural light filters through sheer curtains, and a door leads to a view of the outdoors.

Condo in Bayfield

4.58 out of 5 average rating, 12 reviews

Condo Just Steps from the Lake with Fireplace

A two-story cabin features a wooden exterior with warm orange hues. Multiple balconies are visible, framed by sturdy railings. Snow covers the ground and roof, while a brick chimney adds character to the structure. Dark windows contrast with the bright surroundings.

Condo in Bessemer

4.94 out of 5 average rating, 17 reviews

Lumberjack #3 Trailside Skiing Black River Basin

A cozy living area displays a spacious beige sofa adorned with decorative cushions. A wooden coffee table rests in front, accompanied by a dark wooden shelf with books against a green wall. An ornamental fireplace with stone detailing is located to the right, above which a flat-screen TV is mounted.

Condo in Bayfield

4.71 out of 5 average rating, 49 reviews

Modern Condo Just Steps from the Lake

Numerous sailboats are captured against a clear blue sky, their masts reaching upward into the sunlight. The bright sun creates a halo effect, illuminating the boats and creating a serene atmosphere in the marina setting.

Condo in Bayfield

4.71 out of 5 average rating, 34 reviews

Boatworks #201. Sleeps 8. Pet Friendly. Elevator

An open-plan living space is featured, showcasing a cozy red couch positioned beside a coffee table and a small dining table with wooden chairs. A rock fireplace is visible, and light streams through the windows, highlighting the warm wooden flooring.

Condo in Bayfield

4.67 out of 5 average rating, 27 reviews

Classic Beach Front Condo with Lake Views

Condo in Bessemer

4.5 out of 5 average rating, 10 reviews

Unit #1 Lumberjack- Trailside Black River Basin

Pet-friendly condo rentals

A cozy sitting area features a comfortable sofa with accent pillows, positioned near two windows allowing natural light. A small coffee table is centered on a colorful area rug, complemented by framed artwork on the walls. Soft curtains frame the windows, adding a touch of warmth.

Condo in Ironwood Township

4.5 out of 5 average rating, 4 reviews

Lupinedorf #9

A two-story building with a modern front entrance is surrounded by a landscaped area. The structure features a green metal roof and numerous windows. A gravel parking lot is visible in front, accommodating several vehicles. The expansive lawn adds a touch of greenery to the setting.

Condo in Bessemer

4.8 out of 5 average rating, 20 reviews

Room 212 Nature/Hike/Waterfalls/Powdermill Inn

The open-concept living area features a dining table surrounded by white chairs, complemented by a cozy seating area in the background. Warm light fills the space, highlighting the neutral color palette and textures. A ceiling fan hangs above, adding to the inviting atmosphere.

Condo in Bessemer

4.82 out of 5 average rating, 49 reviews

Sky Top Summer Retreat at Powderhorn Mountain

Top guest favorite

A two-story condo is surrounded by a fresh blanket of snow. Dual balconies can be seen on the second level, framed by light-colored siding. Footprints lead through the pristine snow, and tall trees add a natural backdrop to the property.

Condo in Ironwood

4.97 out of 5 average rating, 32 reviews

Cozy home away from home #2 Schnickelfritz

A welcoming living space features a yellow armchair and a gray sofa, both accented with throw pillows. A wooden coffee table is positioned in front, while a lamp provides gentle illumination. Sunlight filters through yellow curtains, enhancing the neutral wall colors and creating a relaxed ambiance.

Condo in Ironwood

4.96 out of 5 average rating, 112 reviews

Downtown "Yellow Room" at Villages on Aurora

Top guest favorite

Condo in Ironwood

4.97 out of 5 average rating, 96 reviews

Downtown "Blue Room" at Villages on Aurora

A cozy bedroom features a spacious bed dressed in an olive green coverlet. A sliding barn door adds charm, leading to an adjoining area. Soft lighting is provided by a bedside lamp, and a large floral wall art piece complements the room's decor.

Condo in Ironwood Township

4.75 out of 5 average rating, 4 reviews

Summer Time Escapes at Powderhorn Mountain

An open living area showcases modern furnishings, including a dining table with seating, a cozy couch, and stylish chairs. Natural light filters through large windows, and a decorative fireplace adds a touch of warmth. The kitchen features clean cabinetry and a spacious countertop.

Condo in Ironwood

4.91 out of 5 average rating, 115 reviews

Downtown "Red Room" at Villages on Aurora

Condo rentals with a pool

An outdoor pool is visible, surrounded by a concrete deck and offering a bright blue swimming area. Behind the pool, multiple sailboats are docked at a marina, with a clear view of the lake and distant green hills under a lightly clouded sky.

Condo in Bayfield

4.8 out of 5 average rating, 293 reviews

One Minute Walk to Lake Superior. Brookside #3

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.

Condo in Bayfield

4.79 out of 5 average rating, 39 reviews

Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed

A modern kitchen area features a circular marble-topped table surrounded by four upholstered stools on chrome bases. Natural light enters through large windows, illuminating the wooden cabinets and gray flooring. Kitchen appliances are visible, providing a functional yet stylish atmosphere.

Condo in La Pointe

5 out of 5 average rating, 3 reviews

The Madeline Escape

A living area is framed by a stone wall with a fireplace and natural light filtering through window treatments. Comfortable seating is arranged around a wooden coffee table, with throw pillows adding texture. A staircase leads to the upper level, enhancing the home's open design.

4.9 out of 5 average rating, 20 reviews

Whitecap Mountain: Mountain Meadows #4 Nitecap

A cozy studio condo features a spacious bed with dark bedding, subtly accompanied by decorative throw pillows. Natural light filters through two windows near the entrance, illuminating the room. A rug lies at the door, adding warmth to the entryway.

Condo in Bayfield

4.78 out of 5 average rating, 170 reviews

One Minute Walk to Lake Superior. Brookside #10

Destinations to explore