Guest house holiday rentals in Bayfield County

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Top-rated guest house rentals in Bayfield County

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

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Top guest favourite
A wooden balcony is depicted, featuring two chairs and a small table. The sunlight casts shadows over the floorboards, while surrounding trees create a natural backdrop. The space offers a serene view of the forest, inviting moments of relaxation.
Guest house in Two Harbors
4.95 out of 5 average rating, 157 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.

Top guest favourite
Guest house in Cornucopia
4.91 out of 5 average rating, 352 reviews

Sky Fire | Lake Superior Waterfront Retreat

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 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.

Top guest favourite
A spacious guest house is depicted under a light snowfall, featuring a wooden exterior and a well-maintained lawn. A large tree stands in front, and an American flag is visible. Snow covers the roof and ground, creating a serene winter setting.
Guest house in Drummond
5 out of 5 average rating, 41 reviews

Secluded Cabin in the Chequamegon National Forest

Guest House, includes a recently added Bunk House/Game Room just steps from the back door. There are 15 beds total, 1 queen bed, 5 double beds, 9 twin beds of which 5 are bunks. Guest house has 7 beds, Bunk House has 8. A full bath is located in both the Guest/Bunk House areas. Extras include a pool table, card table, golf game, large TV, 100's of movies, popcorn machine and-a 12 place counter top Rent is $350 per night for 6 people. After 6 a $30 charge is added per person per night.

Top guest favourite
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.
Guest house in Ashland
4.99 out of 5 average rating, 400 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 favourite
The image depicts a sandy shoreline bordered by smooth, dark stones along a calm bay. Lush greenery lines the water’s edge, with scattered trees in the background. The overcast sky creates a serene atmosphere, inviting peaceful walks along the beach.
Guest house in Ashland
4.91 out of 5 average rating, 70 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.

A cozy cottage is nestled among snow-covered trees, showcasing a unique exterior with stone accents and a sloped roof. Snow blankets the surrounding ground, creating a serene winter scene. A lantern near the entrance provides a quiet illumination, enhancing the cabin's welcoming appearance.
Guest house in Washburn
4.8 out of 5 average rating, 15 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 house in Bayfield
New place to stay

Modern Private Suite w/Free Breakfast&Free Parking

FREE BREAKFAST AT MANYPENNY BISTRO! Enjoy a peaceful stay in our beautiful guest house with a view of Lake Superior and your own private entrance; offering comfort, privacy, and a relaxing atmosphere. Suite is steps away from our home and a short 5 minute walk to Bayfield. Our charming suite offers a cozy queen-size bed, an additional sofa bed and has a modern kitchenette with a coffee bar. Additionally, enjoy a full, luxurious bathroom with a shower, and a lighted faucet.

Guest favourite
A compact kitchenette features a white stove and oven, complemented by light green cabinetry. A wooden countertop provides space for a kettle and coffee grinder, and a sink is situated beneath a shelf holding glassware. A microwave stands adjacent, enhancing the cooking facilities.
Guest house in Washburn
4.91 out of 5 average rating, 33 reviews

The Lookout Suite

This newly renovated guest house studio w/ kitchenette has a private 2nd fl entrance and outdoor wraparound deck to enjoy the tree tops. House is located on same property as owner. This is a separate outbuilding that you will have all to yourself. Complete kitchenette, stove, fridge, and grill, hammock, outdoor seating, and private spaces to enjoy. Kick back in this calm and cozy space. Dogs are welcome :) There is a friendly Chesapeake Bay Retreiver on the property.

Top guest favourite
A private deck is visible, furnished with a dining table and chairs under a red umbrella. Lush green trees surround the cottage, enhancing the natural setting. A stone pathway leads from the yard to the deck, emphasizing the serene outdoor space.
Guest house in Bayfield
5 out of 5 average rating, 79 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 favourite
A warm and inviting bedroom features a wooden wall design with natural light streaming through multiple windows. A queen-size bed, adorned with a patterned quilt, sits prominently in the space. Nearby, a small dining table and chair complement the cozy decor.
Guest house in Cable
4.87 out of 5 average rating, 160 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.

Guest favourite
A spacious living area features two comfortable couches and a recliner arranged around a wooden coffee table. A stone fireplace is positioned under a mounted TV, with large windows allowing natural light and views of the lake. Soft lighting is provided by a lamp.
Guest house in Cable
5 out of 5 average rating, 6 reviews

Lake Cabin | Fishing + ATV Trail Access

Welcome to Morty’s Place, a clean 3-bed, 2-bath home on a historic Resort. Located directly next to the Yellow Dog Saloon, expect some activity and occasional noise, especially on weekends. Enjoy lake views, a full kitchen, laundry, and dock access. Perfect for guests who appreciate convenience, character, and being steps from the action on Lake Namakagon.

Private room in Bayfield
4.67 out of 5 average rating, 126 reviews

#5 Queen Bed with shared bath, a/c, WIFI.

Homemade food, Whitefish Livers and quaint lodgings are what Greunke's Inn is known for in the Bayfield area (and well beyond!) This 162-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.

Popular amenities for guest house rentals in Bayfield County