Vacation rentals in Chequamegon Bay

4.94 out of 5 average rating, 284 reviews

Two hanging chairs are nestled around a tree, suspended from a wooden structure. A circular wooden table rests on the ground, providing a space to gather. The area is surrounded by tall trees and a natural ground covering of pine needles.

Cabin in Hayward

The Timberjack

Although it's a rustic homage to the lumberjacks and jills of yesteryear, this cabin includes many of the comforts we now enjoy including a queen bed, kitchenette with fridge, hot water, AC/heat, a Keurig coffeemaker, smart TV and charcoal grill. The Timberjack is surrounded by trees right on Lake Hayward and close to downtown Hayward. Launch your canoe just steps from the cabin, walk into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the ideal location!

4.98 out of 5 average rating, 246 reviews

The sauna features wooden benches arranged on three ascending levels. Natural wood walls and a small window provide light, while striped cushions add comfort. A wood-burning stove is located nearby, enhancing the rustic atmosphere.

Yurt in Two Harbors

No Crowds, Sauna, Wifi, Nature, Rest, Pet Friendly

+ 4 miles to Superior Hiking Trail, 6 miles to Betty’s Pies, 9 miles to Two Harbors Lighthouse, 9 miles to Gooseberry Falls, 16 miles to Split Rock Lighthouse + 70 Mpbs Wifi + Electricity + Firewood + Sauna + 2 folding kayaks (will fit in any vehicle) + Sleeps up to 4 + Shower + Space heaters provided + Pet friendly + 16.5 acres of secluded beauty + 1 mile of trails on site + Elopement packages available, visit Wildhaven MN website for more details + See more @wildhavenmn on social media

4.99 out of 5 average rating, 367 reviews

Two white Adirondack chairs are positioned around a fire pit, surrounded by lush greenery and tall trees. The open sky above features bright blue hues, offering a peaceful outdoor setting for relaxation near nature.

Guesthouse in Ashland

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.

Shipping container in South Range

Two modern outdoor chairs face a circular fire pit on a stone patio, situated in front of a sleek black shipping container. Large windows reflect the surrounding greenery, and a standing heater is positioned nearby.

4.98 out of 5 average rating, 147 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Storage containers converted into a Nordic sauna and living space. Set in the woods half a mile from the sandy south shore of LAKE SUPERIOR. Our two-person occupancy and minimal design are curated to re-focus and re-fresh its inhabitants. Located on 80 acres of private land, you will fall in love with the peace and quiet. Whether you’re looking for a romantic couples getaway, spa weekend, or workspace as a digital nomad, Sölveig Stay was designed to spark creativity and relaxation.

4.93 out of 5 average rating, 109 reviews

A geodesic dome is positioned in an open grassy area, surrounded by budding trees and shrubs. The structure features multiple large triangular windows that invite natural light inside. A chimney rises above the dome, indicating the presence of a wood stove for heating.

Dome in Bayfield

Twisting Twig Gardens and Orchard Geodesic Dome

Our rustic glamping dome offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable gardens, apple trees, and rustic accommodations. We are close to great outdoor recreation near Lake Superior and are about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore. Our property is located on 40 acres and is very remote. We are on the edge of thousands of acres of county land. The perfect escape!

A wooden bench is positioned along a scenic waterfront, facing a calm expanse of water. The shoreline is lined with a walking path, and distant hills can be seen across the bay. Two cylindrical bollards are present nearby, adding to the waterfront setting.

4.87 out of 5 average rating, 155 reviews

Bungalow (House) on Chequamegon Bay.

This newly renovated fully furnished home is located within one block from beautiful Chequamegon Bay, Ashland's Oredock Pier, walking and bike trail, boat ramp, and beach. Grab a pole and head down to fish off the Ashland Oredock pier, or pack up for picnic at the beach, launch your boat, kayak or canoe. Take a walk, bike, or run on the walking trails. It is short walk to a few local restaurants and the downtown area. Access snowmobile trails. No pets are allowed.

Superhost

The image captures a rocky shoreline meeting a calm body of water, with vibrant red cliffs rising from the lake. Green foliage crowns the cliff tops, creating a natural frame around the scene. Subtle waves can be observed gently lapping against the rocks.

Condo in Ashland

4.9 out of 5 average rating, 116 reviews

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.

4.98 out of 5 average rating, 158 reviews

A modern A-frame cabin is framed by lush green trees, showcasing a circular window above the entrance. The front patio features two bright blue chairs, inviting relaxation in a tranquil natural setting.

Chalet in Bayfield

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin in the woods with beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

Superhost

A rustic yurt is situated on a wooden deck, surrounded by tall trees displaying autumn foliage. The expansive view reveals a serene Lake Superior, contrasting the vibrant colors of the forest below. The sky is overcast, enhancing the natural ambiance of the landscape.

Yurt in Bayfield

4.95 out of 5 average rating, 347 reviews

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 (mountain bike, cross-country ski and hiking). 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.

4.96 out of 5 average rating, 112 reviews

Cabin in Bayfield

Romantic Vineyard Cabin, Sauna, Plunge Pool

Come and celebrate all that Bayfield has to offer at this quiet vineyard and forest getaway, just 2 miles from downtown. Located in Bayfield's charming Fruit Loop, you'll be surrounded by vines, forest, orchards, and berry farms. The Scandinavian cabin, forest facing sauna with plunge pool, and vineyard sit within 5 acres of woods, secluded from roads and neighbors. The cabin has an occupancy limit of 2 adults and one dog.

4.95 out of 5 average rating, 198 reviews

A bathroom features natural wood paneling, creating a warm atmosphere. A compact vanity with a sink is visible, complemented by a mirror above. A towel bar holds a multi-colored towel. Essential toiletries can be found on the countertop, adding convenience to the space.

Cabin in Washburn

The Long House

My place is close to Lake Superior and the Apostle Islands It is located 2 miles north of Washburn or 10 miles south of Bayfield. Peaceful country setting, the long house is a freshly remodeled mobile home. Sorry, no pets. I have increased the number of guests to six . There are 4 double beds in the cabin. If you are booking with more than 4 guests, please allow for this. Thanks you! Open June 1 - mid October

4.86 out of 5 average rating, 232 reviews

A cabin nestled among tall trees features a wooden deck extending around the front, under the shade of green foliage. Large windows allow natural light to fill the space, while a white vehicle can be seen parked nearby.

Cabin in La Pointe

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin 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, allow guests the feeling of going back in time.

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Other great vacation rentals in Chequamegon Bay

A tranquil pond is surrounded by lush greenery, featuring vibrant lily pads floating on the surface. Rock pathways meander through the garden, leading to various flower beds. Tall trees provide natural shade, enhancing the serene atmosphere of this peaceful outdoor retreat.

Treehouse in Bayfield

4.93 out of 5 average rating, 199 reviews

Boulderridge Treehouse

CalebRating, 5 stars8 months ago

The treehouse was fantastic. We were looking to see some fall colors and get away to a quiet place for some recharging rest. We got just that, with Bayfield right down the street and orchards galore. Beautiful space!

The bathroom is equipped with essential amenities. A shower curtain with a wave pattern provides a coastal touch. A sink and toilet are positioned for convenience, while a plush rug adds a soft element to the tile floor. Natural light filters in, enhancing the space.

5 out of 5 average rating, 20 reviews

A Cozy Getaway in Ashland

RyanRating, 5 stars2 weeks ago

The house was immaculate, everything as stated, we really enjoyed our stay. The only thing that kind of stood out was that there was no top sheets on the beds. Which is not a problem as long as the comforters are getting washed after every guest visit.

A well-appointed bathroom features wooden flooring and a sink area with wooden cabinetry. The toilet is positioned adjacent to the sink, with natural light filtering in through a window, creating a bright and clean space.

Home in Washburn

4.74 out of 5 average rating, 361 reviews

The Red Onion House near Bayfield

KellyRating, 5 stars8 months ago

The host was extremely pro-active with communication, gave suggestions for local things to do and the home was comfortable. We overlooked the fact that there is not a television, but there is WiFi so we played a lot of cards and listened to music.

An open kitchen features dark cabinetry and a smooth stone countertop. Shelves display various dishes and plants, while a stainless steel stove and refrigerator are included. Bright light filters in through a sliding glass door, which provides views of a snowy outdoor landscape.

4.95 out of 5 average rating, 41 reviews

Adventure Homebase

JeanineRating, 5 stars3 weeks ago

This home is a true beauty! The owner has created a lovely oasis with a keen sense of style. Everything was so homey and comfortable. We especially loved cooking in the well-appointed kitchen - top notch! The upstairs great room made us feel like we were in a light and bright treehouse despite being in the woods. It was hard to believe we were just minutes from downtown Ashland. Thank you, thank you for sharing such an amazing home with us (and will you come decorate our house, pretty please?)!!

4.97 out of 5 average rating, 30 reviews

A rustic a-frame cabin is surrounded by tall trees, featuring large glass windows that reflect the natural scenery. A wooden staircase leads to a spacious deck, furnished with several chairs and a table, offering a welcoming outdoor space.

Cabin in Iron River

Hart Haven A-frame on Lake Millicent

CarrieRating, 5 stars2 months ago

This was my second stay at Hart Haven, it was so nice the first time that I knew I wanted to see if it was available for this trip. Emily and Derek are wonderful hosts! The home is always so inviting and homey. Very clean (and I'm a picky person) and they have thought of everything you could need for your stay away from home. So peaceful and relaxing. I will definitely be checking the availability of Hart Haven for my future stays in Iron River. Thank you Emily and Derek!

A detailed 3D floor plan illustrates the layout of the downstairs area. The diagram shows distinct spaces, including a living area with a couch, a dining area with a table, and a kitchen with separate sections. Bedrooms and bathrooms are also marked for clarity.

4.83 out of 5 average rating, 87 reviews

The MacArthur House

Hien JohnRating, 5 stars1 month ago

Very nice house. Big enough for our big family of eight. Very close to central part of town and very close to Bad River Reservation. We really enjoyed our stay and would highly recommend this place.

4.92 out of 5 average rating, 48 reviews

A fire pit made of stones is surrounded by smooth pebbles along the shore. A crackling fire burns brightly, casting warm light against the backdrop of Lake Superior, where waves gently lap at the beach. The sky transitions from cloudy to hues of orange, pink, and blue as sunset approaches.

Cabin in Wakefield

Superior Sunset Cabin

BrunoRating, 5 stars3 weeks ago

Absolutely amazing! We went on a road trip with two friends and spent two nights at Dreamwood. Our goal was to find a secluded place—and this was exactly it. It was a rare and unforgettable experience! Everything was perfect: we found ourselves completely alone, surrounded by nature—an ideal setting to disconnect, recharge, and take our time. The cabin is located right in the Porkies, so hiking trails are just a short drive away. There’s also private access to a quiet beach and the views are absolutely breathtaking—especially at sunset. Tom and Sol were lovely and available when needed. We’ll definitely be back!