Holiday rentals with a hot tub in Bayfield County

Madeline Island Beachfront Condo - up to 10 guests

Relax. Watch the sunset from the back deck, yard, beach or dock. Your condo is located on the quiet end of the main street and within walking distance to everything in downtown LaPointe (including the ferry landing) Sleeps up to 10 adults — master bedroom (1 king), guest bedroom (2 queens), lofted area (2 queens), 2 full bathrooms, full kitchen, laundry, fireplace, Keurigs, TV, WiFi, secure entrance. Second floor. Middle condo. Very quiet. Outdoor deck, dining & BBQ. EV charger available.

Siskiwit Suite Siskiwit Bay Lodge

18 and older are welcome. No pets, due to Innkeeper's allergies. Please note, no early check-in. The Siskiwit Suite has a Calif. King bedroom with a private bathroom, and a bubble tub. There is a full kitchen including coffee maker and living room with balcony deck that also faces west looking out to the lake. Amenities include: a fireplace, and WiFi. An optional lite breakfast offered is fresh fruit daily with either muffins, danish, fruit parfait, or quick bread. Coffee or tea is included.

Bathroom · Hot tub · Backyard

South Shore Chalet | Hot Tub and Game Room

South Shore Chalet is your family fun destination on Bark Point: three bedrooms, a gorgeous loft (with more sleeping space if you need it), indoor and outdoor hangouts galore, plus a game room. The Chalet is packed with creature comforts: a dream kitchen, a hot tub on the back deck, a dedicated workspace, and laundry on site. It's all in a woodsy setting with plenty of room for outdoor frolicking, minutes from Lake Superior beaches and close to Cornucopia and Bayfield and the Apostle Islands.

Hot tub · Outdoor spaces · Quiet

Bayfield Condo on the shore of Lake Superior

With stunning Lake Superior views right in the heart of town, Boatworks 203 is a fantastic spot to experience Bayfield! Walk to the many unique local dining & shopping options as well as the wide array of natural attractions Bayfield has to offer. Lake Superior is within walking distance, along with Bayfield City Dock & Marina, the Madeline Island Ferry Line, fishing, kayaking & boat tours to explore the 22 Apostle Islands. Great golfing, hiking, biking, skiing and orchards are also nearby.

Hot tub · Bathroom · Decor

The Bear Den at Second Wind

Come hibernate at Second Wind. Enjoy the inviting log canopy bed, a two person Jacuzzi, private bath, and engulfing comfy chairs. Venture out to The Gathering Room (lounge) and feel free to use hospitality center, which has a small kitchenette with microwave, fridge and sink. Enjoy our rustic elegance, so close to town, (Ashland) but in the country. Take in a sunset on the front porch or roam our 60 country acres and meet our adorable farm animals. Great for couples, and business travelers.

Hot tub · Outdoor spaces · Breakfast

Hot tub, pet friendly, walk to lake and downtown

Bring the whole crew—without bringing the whole house. Our 4-bedroom, 2-bath Lake Superior stay, newly renovated with a private hot tub and cozy lower-level hangout space. • Private hot tub, fire pit, and outdoor gathering areas • Lower-level lounge/game room for movie nights and rainy-day fun • Kid-friendly touches, plus pet-friendly stays with approval • Ashland neighborhood setting with easy access to town and the lake Settle in, unwind, and make the most of your Ashland getaway.

Hospitality · Cleanliness

One Minute Walk to Lake Superior. Brookside #11

Amazing location! Strong Wifi updated in May 2026. This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. AC, CableTV and fire pit wood provided. 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. The pool an restraunt opens July 1st. 5 minutes to Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

Bathroom · Outdoor spaces · Pool

Telemark North Woods Retreat - 1br/1ba

Perfect for year-round getaways, this comfortable 1BR/1BA condo sits just north of Mt. Telemark and a few miles outside of Cable, WI. It offers a relaxing Northwoods escape with a cozy fireplace, full kitchen, smart TV, Wi-Fi, and pleasant balcony views. The condo provides easy access to snowmobile trails, pontoon rentals, and is minutes from the Birkie and XC ski trails for fantastic outdoor adventures. It sleeps 4 comfortably and includes an in-unit washer/dryer

View · Location · Quiet

Telemark Northwoods Condo - 1br/1ba with Jacuzzi

This comfortable 1BR/1BA condo sits just north of Mt. Telemark and a few miles outside of Cable, WI. It features a private jacuzzi in a dedicated spa room! This perfect year-round retreat offers access to snowmobile trails, pontoon rentals, a cozy fireplace, a full kitchen, a smart TV, Wi-Fi, and beautiful balcony views. It’s minutes from the Birkie and XC ski trails for endless outdoor adventures. The unit sleeps 4 and includes an in-unit washer/dryer

Indoor spaces · Condition · Amenities

Drummond Home, Direct UTV/snowmobile access

Bring the whole family to this great place with lots of room for fun. Nestled in the heart of the Chequamegon National Forest. Enjoy direct access to UTV and snowmobile trails, plus nearby fishing, hunting, skiing, and local events. Clean, comfortable home and true Northwoods charm make this the perfect base for your next adventure. Relax by the firepit, explore scenic trails, and experience the friendly small-town hospitality of Drummond.

Comfort · Pets · Cleanliness

Beti's Base Camp

Looking for a home base for South Shore adventures? Beti’s Basecamp is a sunny tiny home that feels surprisingly spacious. Enjoy a cozy living room with fireplace, fully equipped kitchen, king bedroom, and spa-like bath. Outside, relax in the hot tub, gather around the fire ring, or stargaze from Adirondack chairs. The perfect place to recharge after a day exploring Lake Superior and Wisconsin’s scenic South Shore.

Hot tub · Kitchen · Hospitality

Cozy cabin - perfect for your next 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.

Hot tub · Bathroom · Accuracy