Guesthouse vacation rentals in Bayfield County

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Top-rated guesthouse rentals in Bayfield County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Drummond

5 out of 5 average rating, 29 reviews

Secluded Cabin in the Chequamegon National Forest

Cozy Guest House attache, which sleeps 10 comfortable, in 4 bedrooms, 7 beds and a full bath, kitchen and living room. Plus a recently added Bunk House/Game Room just steps from your back door, with a second full bath. Is has 4 twin/full bunk beds (so 8 additional beds), a pool table, card table, golf game, large TV, 100's of movies, a 12 place counter top and a pop corn machine. Rent is $330 per night for 6 people. After 6 a $20 charge is added per person per night, with a max of 16 people

Guest favorite

Guesthouse in Cornucopia

4.9 out of 5 average rating, 289 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.

Guest favorite

Guesthouse in Two Harbors

4.96 out of 5 average rating, 140 reviews

Swan Forest Loft - trees are your neighbors

Swan Forest Loft is ideal to explore the North Shore of Lake Superior with its 7 state parks. We are located 4 miles from Gooseberry Falls State Park with the start of the Gitchi Gami bicycle trail and 2 miles from a Superior Hiking Trail head. Walk up 15 stairs to a comfortable, spacious 2 bedroom apartment with balcony. It feels like a tree house with modern amenities. The kitchen has a two-burner ceramic stove top, microwave with oven, toaster, hot water kettle, fridge and coffee maker.

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 349 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 favorite

Guesthouse in Ashland

4.88 out of 5 average rating, 42 reviews

Beach Front Hideaway

Attention! G maps suggested route is incorrect. From Hwy 2 - left on 36th, right on Lake Park Rd. Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also deck heaters and gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. TV and Wifi too, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

Guest favorite

Guesthouse in Washburn

4.92 out of 5 average rating, 12 reviews

Glamping Cabin at Whitecap Kayak Learning Center

Your own personal cottage in the forest at Whitecap Kayak Learning Center, a base camp for local kayak guiding and instruction. During the kayak season, our guides stay here. In the off season, we can share it with new friends. You will find a cozy and warm spot in the forest. Expect a small walk to the bathrooms, showers, and running water. You can snowshoe around the property, ski at many local trails or Mt Ashwabay, and enjoy life in the beautiful Washburn and Bayfield area

Guest favorite

Guesthouse in Bayfield

5 out of 5 average rating, 57 reviews

Seclusion in the Pines - A Hidden Gem in Bayfield

Rittenhouse Pines Cottage is a one-of-kind rental! It's a secluded getaway overlooking a ravine surrounded by towering pines. And it's close enough (seven blocks) to all downtown Bayfield has to offer! Since it's the guest cottage adjacent to our home (although it's about 1/2 block away), our three friendly dogs are used to having the run of the place. We'll keep them close to home during your stay but if you aren't a fan of dogs, this may not be the cottage for you.

Guest favorite

Guesthouse in Cable

4.86 out of 5 average rating, 137 reviews

The Bear Den

The Bear Den is a beige/green trim home with a perfect location for all your outdoor ventures, located on the corner of Hwy 63 and Leonard School Rd between Seeley and Cable, WI. This 2- bedroom, 1 1/2 bath unit features Northwoods decor. Relax in private backyard with firepit, free firewood, a gas grill and outdoor furniture. Convenience cooking only with restaurants, gas and grocery shopping nearby Cable, WI, or Seeley, WI.

Private room in Bayfield

4.67 out of 5 average rating, 33 reviews

Manitou Room

Homemade food, Whitefish Livers and quaint lodgings are what Greunke's Inn is known for in the Bayfield area (and well beyond!) This 137-year-old Historic Inn is located in the heart of downtown Bayfield. One block from Lake Superior, the Madeline Island Ferry, Apostle Islands Cruise Service and the several great shops in the downtown area.