Apartment holiday rentals in Ashland County

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

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.

Mapleleaf Loft | Stylish 2BR walk to Silver St

Experience the perfect blend of comfort and convenience at Village on Aurora, a downtown Ironwood retreat! Nestled steps from the City Square and the historic Ironwood Theater, this charming condo offers easy access to Lake Superior, stunning waterfalls, and beautiful beaches. Outdoor enthusiasts will love the nearby trails for hiking, biking, and more. With a stylish interior featuring local Upper Peninsula decor, a queen bed in the master, and a sofa sleeper, this is the ideal base for your ad

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

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

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!

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.

The North Woods Retreat 2

Stay at this fabulous slope-side ski-in/out chalet. Located within steps of the lodge at Big Powderhorn Mtn Resort. 2 Bedrooms with pull out sofa accommodates up to 7 people. Condo offers full accommodations that will exceed expectations. There is a pinball machine, air hockey, and sauna down stairs. Local access to hiking, cross country skiing, snowshoeing and biking trails. Newly updated kitchen (summer 2025). Wildlife is a common occurrence in our yard. No ATVs on property.

One Minute Walk to Lake Superior. Brookside #3

Amazing location! Strong Wifi updated in May 2026. This Condo sleeps 4, King bed & Queen air matress. Full kitchen, balcony, AC, CableTV, fire pit wood povided. Restaurant, bar and pool in July, Aug, Sept. Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. 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. $50 pet fee per stay. 🙂 No smoking allowed.

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.

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!

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.