Vacation rentals in Chequamegon Bay

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Top-rated vacation rentals in Chequamegon Bay

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Guest favorite

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

4.97 out of 5 average rating, 143 reviews

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.

Top guest favorite

The modern cabin features a covered deck with ample seating, including bright red Adirondack chairs positioned around a fire pit. Large windows display warm ambient lighting within, while smoke gently rises from the roof, blending with the surrounding woods.

Cabin in Hayward

4.99 out of 5 average rating, 215 reviews

Hayward Haus, Modern Design w/ Classic Experience

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind This cabin was built in 2021 and host is 13 year "superhost" This is a default "no pets" cabin, however exceptions can be made with permission and a fee. Inquire with host. NEMA 15-40R outlet provided for level 2 EV charging. You bring chord and adapter.

Superhost

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

4.8 out of 5 average rating, 292 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen air matress. Full kitchen, balcony, AC, CableTV, Strong WiFi, fire pit wood povided. Restaurant, bar and pool in July-Sept.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.

Top guest favorite

A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.

Guesthouse in Ashland

4.99 out of 5 average rating, 378 reviews

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.

Top guest favorite

The exterior of the storage container unit is showcased in a serene setting, featuring large windows and a sleek black facade. The surrounding area is landscaped with grass and bordered by a stone path, under a sky painted with soft hues of sunset.

Shipping container in South Range

4.98 out of 5 average rating, 162 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.

Guest favorite

A rustic A-frame cabin is nestled among tall evergreen and birch trees. The exterior features wood paneling, large windows, and a welcoming white door. A patio area with adirondack chairs and a canoe is visible, creating an inviting outdoor space for relaxation.

Cabin in Herbster

4.94 out of 5 average rating, 213 reviews

South Shore A-Frame: Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern Aframe off Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach, 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.

Guest favorite

A small wooden dining table is positioned against the wall, accompanied by two white, spindle-back chairs. A light plaid table runner is placed across the table. Natural light filters in through a nearby window, creating a warm and welcoming dining space.

Home in Ashland

4.87 out of 5 average rating, 165 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

A bright living area features a comfortable gray sofa complemented by a round area rug. A wooden coffee table sits in front of a TV mounted on the wall. Natural light streams through a large bay window, enhancing the welcoming atmosphere.

Condo in Ashland

4.88 out of 5 average rating, 128 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.

Top guest favorite

A small decorative cottage figurine rests in a pot of soil, surrounded by broad green aloe vera leaves. Smooth pebbles are visible among the dirt, contributing to a natural, earthy ambiance.

Chalet in Bayfield

4.98 out of 5 average rating, 165 reviews

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.

Guest favorite

Several yurts are nestled among lush green trees, featuring a blend of blue and tan exteriors. Each yurt is set on a wooden platform with stairs leading to the entrance, surrounded by natural forest floor and dappled sunlight filtering through the leaves.

Yurt in Bayfield

4.93 out of 5 average rating, 195 reviews

Turtle Yurts - Yurt 1

1 Bedroom, 1 Bath, Sleeps 2 Nestled among the north woods, this yurt is a comfortable and unique getaway. The design is a contemporary twist on the traditional yurt, featuring classic yurt elements such as lattice walls and radial rafters, along with modern comforts. The yurt sleeps up to two guests with a queen-size bed sitting under a clear dome to watch the sky above. There is a sitting area, as well as a bathroom, complete with hot shower and flush toilet.

Superhost

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

4.95 out of 5 average rating, 361 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.

Top guest favorite

A Scandinavian-style cabin is elevated among autumn trees, showcasing a welcoming, rustic exterior. Two Adirondack chairs are positioned around a fire pit, which is surrounded by a circle of smooth rocks. The forest setting adds a serene backdrop to this outdoor gathering space.

Cabin in Bayfield

4.97 out of 5 average rating, 128 reviews

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.