Holiday rentals in Stockton Island

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.

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

The Eclectic Apartment on Broad Street

Perfect for a rejuvenating week or weekend getaway! Rest and relax in this amazing space, 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!

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 Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for hiking, biking, fishing, boating and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

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.

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

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.

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.

Hippophile Farm Get-a-way Garden Apartment

The space is a newly renovated apartment on the lower level of our home which is located at our private horse farm on Madeline Island. It is light, bright, with a modern and clean look. It has all the things you need to relax and rejuvenate after spending a day exploring Madeline Island. Enjoy the beautiful woods surrounding the apartment or take a walk to our beautiful stables on the property. Bring your horses if you wish, or just come to enjoy the scenery.

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 Red Onion House near Bayfield

Located 10 minutes s. of Bayfield, this is a casual, comfortable, and welcoming two-bedroom located across the highway from Lake Superior and the Apostle Islands and less than a mile from near the best beaches in the region. Named for the Onion River that flows nearby, this rental has a combo of pine floors & tile. Upstairs kitchen & dining area. Large lawn with easy, plentiful parking. Mt. Ashwabay, Big Top Chautauqua nearby. Outdoor patio + campfire area.