Holiday rentals in Bayfield County

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Top-rated holiday rentals in Bayfield County

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Guest favourite

Treehouse

4.92 out of 5 average rating, 61 reviews

Brilliant Fall Colors at Glass Tree House!

Fall graciously into autumn with your 5* stay at The Glass Tree House. Inclusive with all stays, an exclusive, luxury, wine and cheese cruise aboard the Lady Joanne. Take in the brilliant foliage and reflections on the sparkling waters of the Pike Lake Chain. The Glass Tree House truly is a special, private, couples retreat. Luxury amenities include plush robes/slippers and morning Caribou coffee in bed. Enjoy magnificent sunset views and the call of the loons at twilight on your private deck.

Guest favourite

Home

5 out of 5 average rating, 13 reviews

Private Spot W/ Madeline Island/Lake Views & Sauna

-Modern, Spacious & Bright w/Great Vibes -Ideal Spot atop Bayfield on 1.56 Acres -Views of Madeline Island & Bayfield -Spacious lower level equally bright & airy -On a dead end street w/Ample parking -TV in each bedroom -Gateway to Apostle Islands -Near Downtown Bayfield & Marina - Wood-burning fireplace -Bonus lounge Room W/ a 65-inch TV, Bean Bags & board games - Fully equipped kitchen - Spacious Primary Bedroom W/ en-suite Bathroom & Deck Access **Special Pricing For Monthly/weekly stays

Guest favourite

Cabin

4.96 out of 5 average rating, 103 reviews

Charming private cabin on Superior

Where to go for that peaceful retreat? Look no further than our humble gîte! Sip coffee on the porch, feel the breeze and hear the wind among the trees. Adventures by day: hike, fish or day trip to Grand Marais! The bike trail puts much in reach, jog to Gooseberry, bike to Split Rock, or stroll to Thompson Beach. In the evening the full kitchen is a dream for a foodie, or head fifteen minutes to a brewery. Before bed put up your feet, play a game, read a book, or doze by the fireplace’s heat.

Guest favourite

Flat

4.96 out of 5 average rating, 71 reviews

The Blue Grotto in the heart of Bayfield

The Blue Grotto is an upper level, fully furnished, 1-bedroom, 3/4-bath luxury apartment with private entrance in the heart of downtown Bayfield within walking distance to the ferry, restaurants, shops and beaches. Private deck with lake view. Sleeps 4. Private bedroom has Cal king bed; living room has Murphy bed. Free designated alley parking. A/C available. In-floor heat. Hardwood floors and natural stone tile throughout. Reliable Wi-Fi. Available year round. Check in 3PM; check out 11AM.

Guest favourite

Cottage

4.98 out of 5 average rating, 251 reviews

Lake Superior's Cranberry River Cottage- The Raven

Enjoy beautiful Lake Superior in the 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 Nat'l Forest or venture to Bayfield, home of the Apple Fest, or visit the Apostle Islands Nat'l Lakeshore to see the sea/ice caves.

Guest favourite

Guest suite

4.98 out of 5 average rating, 160 reviews

Come love the south shore of Lake Superior

The Cornucopia Sweet Retreat is a unique open concept living space above Corny Coffee in Cornucopia, Wisconsin. We are just steps from Lake Superior and the Cornucopia beach shops. Lost Creek Adventures is across the street and offers guided kayak tours to the sea caves, and Ehlers grocery store has wonderful deli sandwiches and salads. We are located 20 minutes from Bayfield, Wisconsin and the ferry to Madeline Island. The Cornucopia Sweet Retreat is a no smoking / no pet space.

Guest favourite

Cottage

4.98 out of 5 average rating, 130 reviews

Escape to the Lake at Corny Cottage

Looking for the picture-perfect lakefront cottage that makes you feel like you’re getting away from it all, but still convenient to all Lake Superior’s South Shore has to offer? You’ll find this and more at Corny Cottage! This two-bedroom, one-bath lakefront cottage perfectly combines modern style (and amenities!) with the cozy charm that makes this area so authentic. NOTE: During the winter, the three-season porch section of the cottage will very likely be too cold to utilize.

Guest favourite

Cabin

5 out of 5 average rating, 127 reviews

Superior Sunsets @ The West Slope (Steam Shower)

Our 3 bedroom, 2 bath home is located 1 mile out of Cornucopia and 20 miles from Bayfield. Nestled in a lush forest on a sandstone cliff overlooking Lake Superior, this home features wifi, STEAM SHOWER , a fully equipped kitchen and cozy gas fireplace . Deck with grill and stunning sunset views. Large entertainment room w/ 65" Smart T.V. , POOL TABLE & DART BOARD. Outdoor firepit and picnic table. WE PRACTICE ENHANCED SANITIZING MEASURES DURING COLD IN FLU SEASON.

Guest favourite

Cabin

4.86 out of 5 average rating, 232 reviews

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, allow guests the feeling of going back in time.

Guest favourite

Cabin

4.9 out of 5 average rating, 41 reviews

Cozy cabin - perfect for you winter getaway!

Nestled deep into the beautiful cabin countryside of Douglas County, you’ll find your escape from the hustle and bustle of every day life when you arrive for your vacation at the Harvest Moon Cabin. This cabin sits deep in the woods on 5 acres of soaring pines. With tons of room to roam and 250’ of sugar sand beach and lakefront, this experience is sure to be one you’ll remember for ages.

Guest favourite

Cottage

4.96 out of 5 average rating, 105 reviews

Cozy remodeled cottage in heart of Ashland

Cozy little cottage in quiet neighborhood in Ashland. Only five blocks from Chequamegon Bay. Completely remodeled in 2019. Home features two cozy bedrooms with queen sized beds. All new furniture and appliances. Nice deck with backyard to enjoy your morning coffee or evening meals. Downstairs area with large sectional sofa for kids, teenagers and Dad to get away by themselves!

Guest favourite

Townhouse

4.93 out of 5 average rating, 151 reviews

Cool Condo on Beautiful Lake Owen

3-bedroom 2.5 bath sleeps eight, on Wisconsin's cleanest, most beautiful lake. 2-night minimum stay. Condo includes wood fireplace, flat-screen TV, Blu-Ray/DVD, A/C, small sauna, wraparound deck, private dock, propane grill. Complex has common dock and swim area, small beach, campfire pits, picnic tables, playground and tennis courts (also marked for pickleball).