Guesthouse holiday rentals in Bayfield County

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. The Bear Den is family friendly, with a swingset/playground area for kids, 2- bedrooms, 1 1/2 baths and 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.

Location · Value · Laundry

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.

Value · Family · Comfort

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.

Family · Location · Beach

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.

Family · Location · Condition

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

Location · Kitchen · Heating

Welcome to Bearadise- Secluded Cabin in the woods

Guest House, includes a recently added Bunk House/Game Room just steps from the back door. There are 15 beds, 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 $25 charge is added per person per night.

Value · Location · Pets

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.

Family · Location · Indoor spaces

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.

Location · Wi-Fi · Access

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.

Family · Location · Hiking

Voyaguer Guest Cottage

Located on the historic Château Madeleine Estate, Voyager Guest Cottage offers breathtaking views of Lake Superior and a peaceful setting to relax and experience island life. This charming cottage provides a serene retreat where you can unwind and enjoy the beauty and tranquility of Madeline Island. With its beautiful surroundings and historic setting, Voyager Guest Cottage is an ideal getaway for those looking to slow down and enjoy island living.

Beach Front Hideaway

Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also 2 bikes, fishingpoles, deck heaters, gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. 1 bed, 1 high end sofa sleeper. TV and Wifi, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

Family · Value · Quiet

Pine Cabin - Budget Fishing Cabin

Welcome to Pine Cabin, a modest yet charming two-bedroom retreat nestled within a historic Resort on Lake Namakagon. This cozy three-season cabin offers unbeatable lake views and vintage Northwoods charm, perfect for a fishing weekend or a quiet lakeside escape. Located along County Highway D, you'll be steps from the future Yellow Dog Saloon and right next to Maple Cabin and Morty’s Place.

Location · Value · Wi-Fi