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.

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.

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.

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.

Madeline Island Beachfront Condo - up to 6 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 6 adults — master bedroom (1 king), lofted area with (2 queens), 2 full bathrooms, full kitchen, laundry, fireplace, Keurig, TV, WiFi, secure entrance. Second floor. Middle condo. Very quiet. Outdoor deck, dining & BBQ. EV charger available.

Telemark Point Lakefront Condo - 2br/2ba

Discover Lake Namakagon at this stylish 2BR/2BA lakefront condo in Cable, WI! Ideal year-round getaway with dock access, snowmobile trails, pontoon rentals, cozy fireplace, full kitchen, smart TV, Wi-Fi, and scenic balcony. Just steps to the lake for boating and fishing, and close to Birkie and XC ski trails. Sleeps 6, with in-unit washer/dryer. Professionally cleaned and hosted by Telemark Northwoods Lodging. Begin your Northwoods escape today!

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.

Hot tub, pet friendly, walk to lake and downtown

Bring the whole crew—without bringing the whole house. Designed for families and groups up to 10, with the little things covered so you can pack less and vacation more. • 4 bedrooms + 2 full baths • Private hot tub • Fire pit + outdoor gathering spaces • Lake Lounge with games + movies • Kid + dog friendly Explore Lake Superior, Bayfield & the Apostle Islands by day, then come home to a house made for time together.

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.

Madeline Island Beachfront Condo - up to 4 guests

Relax. Watch the sunset from the back deck, yard, beach or dock. Your suite 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 4 adults — hotel set up: 2 queen beds, full bathroom, Keurig, TV, WiFi, secure entrance. Second floor. Middle condo. Very quiet. Outdoor deck, dining & BBQ. EV charger available.

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.