Holiday rentals with a kayak in Watersmeet Township

Lakeside Loft, Roof Deck + Sauna

Wanderloft, designed by architect David Salmela, combines modern Scandinavian design with the natural beauty of Wisconsin's Northwoods. Located on one of Vilas County's highest points, this cabin offers stunning 360-degree views from multiple levels, overlooking Manuel Lake and 9.4 acres of land. Beyond its striking design, Wanderloft is defined by its profound sense of peace and quiet - where natural beauty and thoughtful architecture create space for rest, creativity, inspiration, and renewal.

Cottage on High Lake

Dog-Friendly Lakefront Cottage w/ Dock, Kayaks, Canoe, and Snowshoes Experience everything the Boulder Junction area has to offer at this cottage located on beautiful High Lake in Land O’ Lakes. This rental is ideally situated at the gateway to year-round outdoor adventures, whether you're looking to get out on the water, explore the woods, or race through the snow. This home features lakefront access with level fisherman frontage and a private dock. At night, enjoy the wood-burning fireplace.

New Listing! Near Lakes & Trails, Hot Tub, Pets OK

Surrounded by forest and near some of the area’s beautiful lakes, Dawson’s Den blends rustic charm with the comforts of home. Whether you're exploring trails, relaxing in the hot tub, or unwinding in the cozy screen room, this cabin is the perfect escape. • Private hot tub • Outdoor firepit • Three-seasons screen room with cozy seating + helmet rack • Central A/C • Smart TVs + DVD library + Board games • Electric fireplace • Propane + Charcoal grill • Parking for two trailers • Kayaks included

Eagle’s Wings Cabin

Charming full log cabin nestled on 6 wooded acres with full recreation, private lake access. This beautiful property comes with 2 bedroom, one bath with a shower, fully stocked kitchen. Baseboard heat and pellet stove. Outside there is a wrap around deck, a gas grill, a fishing boat, canoe, 2 kayaks, and a fire pit. Supper clubs, grocery store, gas station, bowling alley, pub/restaurant only 3 miles away. Many trails, UTV, snowmobile, hiking near by. Snowmobiling trails are is top notch!

Private Lakefront Cabin Near Eagle River

Nestled on a private wooded 1+ acre lot, this cozy Northwoods cabin offers seclusion, comfort, and classic up-north charm. With 158 feet of private waterfront, enjoy lake views, morning coffee by the shore, and peaceful sunrises. Inside features a warm, inviting space with a refreshed kitchen. Outside, relax in the spacious yard or around the fire. Located on snowmobile trails and near great fishing and hiking. Just 5 minutes to Land O’ Lakes and 20 minutes to Eagle River. Private boat launch.

North Woods Pristine Lake Paradise!

** Note - This wonderful northwoods cabin rents for a minimum of 3 consecutive nights. ** Your own private guest cabin on 6 private acres overlooking crystal clear Big Portage Lake. Sand beach, canoes, kayak, great lake views! Refrig, coffee maker, microwave and toaster, but no kitchen (great restaurants nearby). Come and go as you please. Host is usually on property, residing in main house. Kids over 8 years welcome. NO pets, jet-skis, ATVs, fireworks, loud music or powerboats, please.

All-seasons lake retreat. Northwoods in comfort.

Muskellunge Lake. Great location to enjoy all the Northwoods has to offer. Only minutes to Tomahawk (<5), Rhinelander (15) and Minocqua (20). 150' frontage w/ private pier. If you love the idea of a cabin but don't want to rough it, this is the place for you! 3 large comfortable bedrooms, spa-like master bath, two gas fireplaces, and central air. Step onto the large screened-in porch overlooking the lake to listen to the loons, but without bugs. House is on Snowmobile/ATV route.

Retreat B on Little Spider Lake (Towering Pines)

Our property offers a Peaceful Getaway in a Resort Setting on a Quiet Lake. "Great Location", "Amazing Views", "Clean", "Cozy", "Perfect", "Peaceful", "Comfortable", and "Relaxing" are what we repeatedly hear from our guests after their stay. The Heart of Vilas County Bike Trails and numerous Hiking trails are just minutes away. The #5 Snowmobile/ATV trail runs across the front of the property along Hwy 51 and we are surrounded by many area lakes and the Northern Highland State Forest.

National Forest Lakeside Retreat

Escape to this beautiful cabin nestled in the woods on a serene lake. With its cozy layout and large windows, you'll feel right at home surrounded by nature's beauty. Enjoy breathtaking views of the dark sky at night and wake up to the peaceful sounds of the National Forest. Explore endless adventures with hiking, ATV, and snowmobile trails just steps away. Unwind on the deck and take in the tranquility of this hidden gem. Book your getaway now and experience the ultimate retreat.

Lakefront, near downtown and trails! Dog-approved

Our Breakfast at Tiffany House sits on Yellow Birch, has dock/water access for your toys, is a short walk from downtown shopping and events. You'll find everything you need, including tons of extras to make you feel at home, with lake home themes and pops of Tiffany Blue throughout. Room for parking trailers, close to snowmobile/ATV trails and snowmobile/boat rentals! We supply 2 adult kayaks, 1 children’s kayak, 2 inflatable paddle boards, and life jackets. Come Getaway With Us!

Lakefront Cottage on Upper Post Lake

NO PETS! Enjoy beautiful sunsets from this year-round lakefront cottage on Upper Post Lake in the Wisconsin north woods. Fish, swim, and water ski from the private dock. Relax by the fire and watch the eagles and listen to the loons. Located on the ATV and snowmobile trails. Walking distance to the local bar and grill. Updated two-bedroom house with full kitchen. Lovely getaway for a weekend or longer! No pets allowed!

Lakefront Cabin • Dock • Kayaks • Sunset Views

Escape to Lac Vieux Life, a lakefront cabin on beautiful Lac Vieux Desert. Enjoy a private dock, 3 complimentary kayaks, great fishing, stunning sunsets, a fire pit, wood-burning fireplace, and family-friendly games. Sleeps up to 6 adults + 2 children with 2 bedrooms and a loft bunk room. Dog-friendly (fee applies), fully equipped kitchen, Weber grill, Wi-Fi, and year-round Northwoods adventures.