Holiday rentals in Chequamegon Bay

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Top-rated holiday rentals in Chequamegon Bay

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Guest favourite

Cottage in Herbster

4.91 out of 5 average rating, 279 reviews

Lake Superior's Cranberry River Cottage- The Wren

Enjoy beautiful Lake Superior in this clean cozy modern cottage located in the quaint little town of Herbster where the Cranberry River enters. It's just a short couple blocks to the beach and playground. Enjoy the beautiful sunsets, swimming, boating, kayaking, biking, fishing, hunting, and skiing with ATV and snowmobile trails nearby. Explore the Chequamegon National Forest or venture to Bayfield, home of the Apple Fest, or visit Apostle Islands National Lakeshore to see the ice/sea caves.

Guest favourite

Guest house in Cornucopia

4.9 out of 5 average rating, 265 reviews

Waterfront Lake Superior's South Shore, "Sky Fire"

Relax with expansive views of Lake Superior as you bask in the glow of the wood burning fireplace's radiance. Waves echoing off the brownstone cliff upon which this special home is perched, absorb the splendor of bald and eagles soaring only feet away. Minutes from your nest is Meyer's Beach, the common entry point to begin your kayak or hiking excursion to the sea and ice caves of this, the greatest of all lakes. Bike, hiking, motorsports and XC ski trails abound. Rest or play. It's all here.

Superhost

Apartment in Bayfield

4.79 out of 5 average rating, 315 reviews

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 , BBQ, fire pit, and bikes. 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 club Brewery.

Guest favourite

Cabin in Ironwood

4.95 out of 5 average rating, 420 reviews

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.

Guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 310 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.

Guest favourite

Tiny home in Saxon

5.0 out of 5 average rating, 136 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.

Guest favourite

Yurt in Bayfield

4.9 out of 5 average rating, 140 reviews

Turtle Yurts - Yurt 2

1 Bedroom, 1 Bath, Sleeps 2 Nestled among the north woods, this yurt has everything you need for 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 amenities. 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 shower and flush toilet.

Guest favourite

Home in Ashland

4.88 out of 5 average rating, 122 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

Yurt in Bayfield

4.96 out of 5 average rating, 291 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.

Guest favourite

Cabin in Washburn

4.95 out of 5 average rating, 178 reviews

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

Guest favourite

Flat in Ashland

4.95 out of 5 average rating, 150 reviews

The Garland City Downtown Apartment

1920s, craftsman and art-deco-inspired apartment, furnished with antiques, located in the heart of Ashland’s Main Street Historic District. Ditch the car and walk to local amenities like the grocery store, brewpub, bars, restaurants, shops, library, and movie theater. View Ashland’s downtown murals. The Lake Superior waterfront is steps away...where you can stroll the shoreline path or bicycle the 9-mile town loop.

Guest favourite

Flat in Ashland

4.84 out of 5 average rating, 103 reviews

Main street view apartment

The apartment is on the edge of the business district. A short walk to all the attractions. A quick two block to Lake Superior, or a block from the local brewery. Local bakery also only a few blocks away, as well as all of Ashland's local businesses. As you enter or exit the town, it is only one block off of US Highway 2.and makes finding your destination much easier.