Family-friendly holiday rentals in Bayfield

4.93 out of 5 average rating, 263 reviews

A rustic A-frame cabin is set amidst tall trees, featuring a stone pathway leading to a fire pit with stacked logs. Outdoor seating is visible, and a patio umbrella provides shade, enhancing the inviting outdoor space.

Cabin in Herbster

South Shore A-Frame | Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern A-frame on Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach (1/4th mile down road), breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.

A charming green house is framed by colorful gardens filled with various flowers. The inviting porch is adorned with seating, and large windows reflect natural light. The home showcases classic architectural elements under a clear blue sky, providing a welcoming appearance.

4.95 out of 5 average rating, 153 reviews

The Eclectic Apartment on Broad Street

Your jumping off point to all things Apostle Islands National Lakeshore. Rest and relax , one block from the public sauna and pool, where you will wake up to sunrises over Lake Superior and end your day on the deck with a glass of wine or a good book. The bedroom and living room have amazing natural lighting. Local coffee and a full kitchen, as well as laundry, free parking, Roku TV and a custom tile shower offer all of the comforts of home. The perfect romantic getaway, or a retreat for one!

4.97 out of 5 average rating, 180 reviews

The cabin's striking exterior features large cedar beams and expansive windows, blending seamlessly into the natural surroundings. A screened-in patio offers a view of the woods and lake, while a gas grill is positioned nearby for outdoor dining.

Cabin in Herbster

Cedar Ridge | Hand-Crafted Cabin with Lake Views

This newly built cabin will take your breath away. You’ll find the perfect blend of Northwoods rustic charm and creature comforts in this 3 bdrm cabin nestled in the woods overlooking Lake Superior’s Bark Bay. You’ll fall in love with all the care & attention its owners have put into every detail. From the stunning cedar beams that provide the backdrop to the incredible lake views to the hand-crafted interior woodwork and the beautiful kitchen, you will see how unique and special this cabin is.

4.98 out of 5 average rating, 124 reviews

A spacious outdoor deck with a cozy lounge area featuring a modern propane fireplace surrounded by plush seating. The deck is lined with trees, providing a serene, private setting. String lights are seen above, adding ambiance to the inviting space for relaxation.

Cottage in Bayfield

Bayfield Fruit Loop Retreat - Main Cottage

Welcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, Wisconsin. The property allows you to savor a peaceful & quiet northwoods experience but still minutes from several attractions & historic downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where a

4.97 out of 5 average rating, 433 reviews

The exterior of an artisan-crafted lake home is shown at twilight, featuring large windows that reflect the soft evening light. Surrounded by greenery and wildflowers, a stone pathway leads to the entrance, enhancing the natural setting.

Home in Herbster

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!

4.98 out of 5 average rating, 373 reviews

The cabin exterior features logs and a screened porch, offering shaded seating. A wooden deck wraps around, and steps lead up to the entrance. A propane grill is visible, and greenery surrounds the space, providing a secluded atmosphere.

Cabin in Bayfield

The Copper Squirrel of Little Sand Bay DogsWelcome

A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin was recently completely renovated (Mar/April 2025)from log to log and is stocked with everything you'll need for your stay. It has all new appliances, furniture, fixtures, bathroom, cabinetry. 💚 It is the perfect homebase to relax after a long day of hiking Frog Bay, Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

4.87 out of 5 average rating, 199 reviews

Cottage in Bayfield

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts. Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen • Boat Slip Rental Available

The open living area features large south-facing windows allowing natural light to fill the space. A comfortable gray sofa and a supportive chair are arranged on a patterned rug. A small table is set up for work or dining, complemented by greenery from nearby plants.

5.0 out of 5 average rating, 104 reviews

Sunny + Spacious Rental in the Heart of Bayfield

1 bedroom + den with additional queen bed in the heart of Bayfield's historic district, just steps to downtown shops, restaurants, and beaches. Located in the lower level walkout of our duplex, this private + newly remodeled apartment boasts bright spaces, big windows, and comfy furniture for lounging. Take in glimpses of Lake Superior from the open concept living room/kitchen/dining area and enjoy your morning coffee from the covered veranda while enjoying the fresh Lake Superior breezes.

4.95 out of 5 average rating, 409 reviews

A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.

Yurt in Bayfield

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (CAMBA single track and Mt Ashwabay nordic ski and hiking trails). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods. Yurt access is 3/4 mile uphill.

4.99 out of 5 average rating, 166 reviews

Cottage in Cornucopia

Borealis Cottage by Siskiwit Bay

Borealis Cottage sits on a 2-acre, private, wooded lot in the sustainably designed Sawgrass Community of Cornucopia. Light-filled cottage with open floor plan includes a sleeping loft, screened porch, gas fireplace, and fully-equipped kitchen. A quick, quiet walk from the cottage takes you to a private wooded path with access to Cornucopia Beach on Siskiwit Bay. Explore the Apostle Islands National Lakeshore--our cottage is located 4 miles from Meyers Beach and 20 miles from Bayfield.

4.79 out of 5 average rating, 309 reviews

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

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.

A cozy living area features a comfortable gray sofa and a plush red armchair, accompanied by a wooden coffee table. The room is divided into a sleeping area with a queen-size bed, adorned with light-colored bedding. Soft lighting enhances the welcoming atmosphere.

4.84 out of 5 average rating, 149 reviews

Lake Superior Hillside Suite 1 • Walk Downtown

Relax in this peaceful hillside suite overlooking Lake Superior and Madeline Island. Wake to beautiful sunrise views and enjoy a short walk to downtown Bayfield’s restaurants, shops, marina, ferry, parks, and hiking trails. This cozy cottage-style apartment is the perfect home base for exploring the area while enjoying a quiet coastal retreat. 1 dog allowed (up to 60 lbs). Pets may not be left unattended in the suite. Please review house rules for details.

Popular amenities for Bayfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A cozy living area features a beige sofa positioned next to two wooden chairs. A stone fireplace adds character to the space, while large glass doors lead to a balcony with outdoor seating. Natural light filters in, enhancing the warm ambiance.

4.84 out of 5 average rating, 56 reviews

Bayfield Condo on the shore of Lake Superior

5.0 out of 5 average rating, 21 reviews

Home in Brule

Brule River Secluded Getaway • Hot Tub

Bed and breakfast in Bayfield

A warm living area features plush seating options including a beige sofa and two maroon armchairs. Natural light enters through windows with beige shades, illuminating a floral rug on hardwood flooring. A dining area with wooden furniture is visible in the background.

Rittenhouse Cottage (Sleeps 3)

4.85 out of 5 average rating, 20 reviews

A spacious living area features a large sectional sofa facing a contemporary TV and a wood stove. Natural light fills the room through expansive windows, offering a view of the lake and surrounding landscape. A fan hangs from the wooden ceiling, adding to the cozy atmosphere.

5.0 out of 5 average rating, 22 reviews

Lake Superior Retreat: Waterfront Views + Access

4.86 out of 5 average rating, 49 reviews

A serene lakeside view offers gentle waves lapping against rocky shoreline. Lush green grass and wildflowers frame the foreground, leading to a clear view of the sparkling water. Trees line the back, adding a natural boundary to the scene under a partly cloudy sky.

Home in Two Harbors

North Shore Escape

Holiday home in Two Harbors

A row of welcoming condos is positioned along the shore of Lake Superior, surrounded by lush greenery and rocky terrain. Each unit features a private deck and large windows, offering scenic views of the lake and inviting natural light into the spaces.

Lakeside Condo - Sleeps 8

4.84 out of 5 average rating, 38 reviews

5.0 out of 5 average rating, 87 reviews

Penthouse w/pool & hot tub

4.92 out of 5 average rating, 25 reviews

An open living area features a vaulted wooden ceiling and large windows providing expansive views of Lake Superior. Comfortable seating is arranged around a central coffee table, while a dining table for six is visible in the background. A stone fireplace offers a cozy focal point.

Home in Two Harbors

Spacious Lake Superior Cabin In Two Harbors

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 369 reviews

Guesthouse in Cornucopia

Sky Fire | Lake Superior Waterfront Retreat

4.74 out of 5 average rating, 399 reviews

A red two-story house with a green metal roof is set within a natural landscape. A gravel driveway leads up to the home, which features several windows and a large yard. A parked blue car is positioned near the entrance.

Home in Washburn

The Red Onion House near Bayfield

4.9 out of 5 average rating, 154 reviews

The exterior of the unit is framed by mature trees, featuring two private patios with seating. Steps lead from the grassy area to the wooden deck, which is designed for relaxation in a tranquil setting. Large windows reflect the surrounding greenery.

Apartment in La Pointe

Treehouse 1 on Madeline Island

4.98 out of 5 average rating, 109 reviews

Home in Iron River

Guest House

4.99 out of 5 average rating, 240 reviews

Cottage in Herbster

Applegate Cottage - South Shore of Lake Superior

4.92 out of 5 average rating, 119 reviews

The modern cabin is situated along a rocky shoreline, surrounded by lush greenery and tall trees. The clear blue waters of Lake Superior reflect the vibrant sky, enhancing the natural beauty of the landscape. Scenic views stretch along the coastline.

Cabin in Two Harbors

Secluded Lake Superior Cabin next to Gooseberry

4.8 out of 5 average rating, 136 reviews

A rustic cottage is surrounded by colorful autumn foliage, showcasing its wooden exterior and A-framed roof. A large porch with steps provides entry, and a pathway leads through the grassy yard, where scattered leaves complement the natural setting.

Cabin in Port Wing

Cozy South Shore cottage near Lake Superior

4.97 out of 5 average rating, 146 reviews

A two-level cottage is shown from an elevated perspective, featuring a sloped roof and a walkout balcony. The balcony overlooks a lush, green landscape, highlighting the expansive views of the forest and Lake Superior in the distance under a clear blue sky.

Cabin in Two Harbors

Gokotta Cottage: Cozy forest retreat w/ lake views

Family-friendly home rentals with a pool

4.83 out of 5 average rating, 83 reviews

Brookside Hideaway #6

4.79 out of 5 average rating, 28 reviews

Brookside Hide-A-Way #2, Port Superior, Bayfield

4.83 out of 5 average rating, 47 reviews

Condo in Bayfield

Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed

4.96 out of 5 average rating, 52 reviews

Superior Lakefront Studio | Pool • Hot Tub • Sauna

4.97 out of 5 average rating, 32 reviews

Pool & hot tub, condo, views, lakeshore

5.0 out of 5 average rating, 7 reviews

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

The Madeline Escape

4.89 out of 5 average rating, 62 reviews

Lakefront 2 Queen Fireplace Studio~Pool/Hot Tub