Pet-friendly holiday rentals in Bayfield County

One Minute Walk to Lake Superior. Brookside #3

Amazing location! Strong Wifi updated in 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-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.

Stunning Bark Point Home on Superior's South Shore

One of a kind, open/loft-concept (see pics: it really is open) artisan-crafted lake home on Superior's south shore: paddle in summer/ice hike in winter. Breathtaking sunsets. 300+ feet of private shoreline or short walk to public beach. Great kitchen. Up to 8 people and most dogs welcome - PET FEE: pets are an extra $25 (there is a place to leave this next to the house manual on the kitchen counter) Scenic huge patio with built-in fire pit (BYO firewood) We hope you love it as much as we do!

Sky Fire | Lake Superior Waterfront Retreat

Relax with expansive views of Lake Superior as you bask in the glow of the wood burning fireplace's radiance. Waves echoing off the brownstone cliff upon which this special home is perched, absorb the splendor of bald and eagles soaring only feet away. Minutes from your nest is Meyer's Beach, the common entry point to begin your kayak or hiking excursion to the sea and ice caves of this, the greatest of all lakes. Bike, hiking, motorsports and XC ski trails abound. Rest or play. It's all here.

Start Line Inn on Bike & XC Trails Powered by Sun

Silent Sport & outdoor enthusiasts. Rejuvenate in nature. Powered by Solar Energy. Couples getaway or fun with family/friends. Ski, Bike & Hike in/out. Trails for XC, mountain & fat biking & hiking. Scenic routes for road cyclists. 20% OFF at Start Line Services Bike & XC Shop, on property. Water access nearby. Located at American Birkebeiner Start. Cabin charm with modern comforts. Business grade WiFi Work & Play! Wish to reserve more than 6 months ahead? Please send message.

Cozy South Shore cottage near Lake Superior

Enjoy the splendor of Lake Superior at our cozy, rustic cottage near Port Wing, WI. Situated halfway between Duluth/Superior and Bayfield, it's the perfect location to visit all your favorite South Shore locations. There's no need to choose between privacy & the difficulties of accessing remote properties. Our cottage is located within 68 acres of private, wooded wilderness. Yet since we're next to the Wisconsin Lake Superior Scenic Byway (Hwy 13), it's easy to get wherever you want to go!

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, all appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, with a heated tile floor, walk-in shower. Towels, shampoo/conditioner/bodywash are provided. King bed in loft and NEW king bed on main floor. Smart TV, wifi. Books, games The Woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

Lake Delta Deer Trail Delight

Deer Trail Cabin 6 is on the shore of Lake Delta in the heart of Delta. Popular day trips include the Hayward lakes area, the Apostle Islands National Lakeshore and Bayfield or exploring the endless trails, waterfalls and wilderness within Bayfield County. This is a furnished two bedroom cabin with full kitchen and bath. Great view of Lake Delta and next to swimming beach. There is direct ATV trail access from your cabin but we ask that you do not ride around the property.

Woodland Escape | Charming Cabin Steps to the Lake

Perfect for the whole family, including your canine companions! Woodland Escape combines the authentic Northwoods cabin vibe with modern comforts & a touch of whimsy (llama ottoman, anyone?). Located on a wooded 2.5 acre lot that is a short 5-minute walk to one of the area's loveliest beaches, this is a perfect place to relax, recharge, and reconnect with your loved ones. And it's in the perfect location on the South Shore with access to trails, towns, and the Big Lake!

Parking, Walk to Town, King Bed - The Cable Cabin

Locally owned and managed. Our cabin is tucked behind pines right on Highway 63 in Cable. Full off street, private parking w/ room for trailers and toys, plus full locked gear room in basement. Easy walking distance to everything in Cable. It can sleep 5-6, but makes a great space for 2-4. 3 mi from the Birkie start, 2.5 mi from the North End Cabin. ATV & Snowmobile right from the driveway. Full furnace for heat and central air conditioning for those hot summer days!

Lake Superior Getaway. Hillside Suites Unit #1.

Your inland coastal getaway in beautiful Bayfield, WI. Keep it simple at this peaceful and centrally-located place. Cottage apartment tucked into the hillside with wonderful views of Lake Superior and Madeline Island. Walking distance to restaurants, parks, hiking trails, ferry, and marina. We allow 1 dog up to 60 lbs. Dogs are not allowed to be left unattended in room (even if kenneled). Please read house rules section if bringing a pet for other guidelines.

the Cottage on Long Lake

Whether you are looking for a quiet get-away or unlimited outdoor activities, our four bedroom cottage will meet your needs! It is located on Long Lake just east of Iron River, WI, in Bayfield County. Fishing, bird watching, biking, cross-country skiing and hiking are great "silent sports" but the cabin is also only a few blocks from the Tri-County Corridor (the start of the Whistlestop Marathon) for exceptional dirt biking, four-wheeling and snowmobiling.

Applegate Cottage - South Shore of Lake Superior

Applegate cottage is an adorable cottage located just a short walk from the beautiful beach in Herbster, Wisconsin on the Lake Superior Scenic Byway. Whether you like hiking, biking, kayaking, skiing or just relaxing, there’s something nearby for everyone. Bayfield County has orchards, wineries, the Apostle Islands, sea caves, boutique shopping, waterfalls, great restaurants and so much more! Best of all…the sunsets! And, every season brings it’s own beauty!