Holiday houses in Stockton Island

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Top-rated holiday rentals in Stockton Island

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Superhost
A yurt is nestled among trees, featuring a circular white top and green walls. A small wooden deck extends from the entrance, providing a welcoming outdoor space. The surrounding area is landscaped with lush greenery and scattered underbrush.
Yurt in Bayfield
4.88 out of 5 average rating, 551 reviews

Bayfield Rustic Yurt 1 (Evergreen)

Explore thousands of acres of the Bayfield County Forest and enjoy endless miles of exceptionally maintained non-motorized recreational trails. The yurt has direct access to CAMBA mountain bike trails and Mt. Ashwabay ski trails. The landscape is also spectacular. Take in the panoramic views of Lake Superior and the Onion River valley. This is a rustic, minimally maintained yurt set in the middle of the county forest, so come prepared to relax, unwind and explore the wonders of the north woods.

Top Guest favourite
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
4.97 out of 5 average rating, 430 reviews

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!

Top Guest favourite
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
4.99 out of 5 average rating, 120 reviews

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

Top Guest favourite
A serene cabin exterior is nestled among tall trees and vibrant yellow wildflowers. The wooden deck invites outdoor relaxation, while the expansive view of Lake Superior is visible beyond the greenery, creating a tranquil and picturesque setting.
Cabin in Beaver Bay
4.95 out of 5 average rating, 204 reviews

Superior Lakefront Cabin - Beach - Trail Access

Lakefront cabin located at the site of historic Captain's Cove Boat Tours. The interior has been newly renovated to include modern fixtures and finishes to an open floor plan that maximizes the breathtaking views of Lake Superior. For epic panoramas of the lake head out to the yard for a hot cocoa by the bonfire, or a glass of wine at the charming deck on the bluff's edge. Or take the path down to the private beach featuring 280' of pebble and sand shoreline. Access to bike and hiking trails.

Guest favourite
Home in Hurley
4.96 out of 5 average rating, 162 reviews

Cedar Hill Retreat, King Bed, 108 Acres of Privacy

Winding up the driveway you are greeted by a home located on 108 acres of privacy, yet only 8 miles from town! This place is a clean (enhanced cleaning routine), fresh, and relaxing with breathtaking views! With enough space for a whole group or private couple getaway, this home offers the perfect opportunity to make memories lasting a lifetime. Gather around the wood stove after a long winter day full of activities available close by, or relax on the back deck watching the sun set in summer!

Superhost
A serene lakeside view captures the sun setting over calm waters. Two rustic chairs are positioned on the shore, framed by trees. The horizon glows with warm colors, reflecting off the lake's surface, while surrounding foliage adds to the tranquil atmosphere.
Home in La Pointe
4.78 out of 5 average rating, 23 reviews

Private lakefront retreat

Welcome yourself to the tastefully remodeled, Scandinavian-designed lake house with a sophisticated modern touch nestled on North Shore. Views of Lake Superior, Apostle Islands, and forested meadows seen from wrap-around, front porch & deck. Wood burning stove in open floor plan living & dining room perfect for family entertaining. Brand new appliances in updated kitchen connects to a large, screened-in porch. Enjoy the outdoors in large yard complete with fire pit & BBQ, or nearby hiking

Top Guest favourite
Cottage in Bayfield
4.87 out of 5 average rating, 197 reviews

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

Top Guest favourite
The cabin's exterior displays a modern A-frame design, surrounded by a lush forest. The patio area features blue adirondack chairs and a small table, inviting relaxation amidst nature. A circular window enhances the aesthetic, creating a connection between indoor and outdoor spaces.
Cabin in Bayfield
4.99 out of 5 average rating, 223 reviews

The Acorn of Little Sand Bay Dog Friendly

Modern-rustic, Aframe on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, glass stove top, air-fryer 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 gel memory foam bed on main floor. Smart TV, wi-fi. Woodstove heats the cabin perfectly as the main heat source. All wood is provided for woodstove and firepit. There is a minisplit heat/ac unit.

Guest favourite
An aerial view captures the expansive a-frame cabin, showcasing its unique triangular architecture and stone chimney. Surrounded by lush greenery, large decks extend from the structure, providing outdoor space. The soft glow from the windows hints at a warm, inviting interior.
Cabin in Two Harbors
4.98 out of 5 average rating, 243 reviews

Wild Pines Cabin: A-frame w/ Lake Superior views

Enjoy off-grid vibes while being right in the heart of the North Shore. Located 5 minutes from Split Rock Lighthouse, Wild Pines Cabin is a completely renovated 1974 a-frame that sits atop 40 private acres overlooking Lake Superior. During your stay, hike through the property, catch glimpses of wildlife, sip coffee by the fire while taking in the sunrise over the lake, or step out to nearby Gooseberry, Black Beach, or Tettegouche. A beautifully private north woods retreat any time of year!

Superhost
A spacious cabin nestled among trees showcases large peaked windows and a welcoming deck. Sunlight filters through the leaves, illuminating the cabin's wooden exterior and the surrounding forest foliage.
Cabin in La Pointe
4.84 out of 5 average rating, 267 reviews

7 Pines La Pointe on Madeline Island

Looking for Island serenity? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin, tucked in the woods close to beaches, town and the golf course, offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, which can give guests a feeling of going back in time.

Top Guest favourite
A sitting area features a futon draped with a cozy blanket, complemented by colorful accent pillows. A spacious bed with a patterned coverlet is positioned nearby, while a countertop with bar stools creates an inviting space for dining or gathering.
Tiny home in Saxon
4.97 out of 5 average rating, 310 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

Superhost
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, 390 reviews

One Minute Walk to Lake Superior. Brookside #11

Amazing location! Strong Wifi updated in May 2026. This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. 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. The pool an restraunt opens July 1st. 5 minutes to Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

Popular amenities for Stockton Island holiday rentals