Vacation rentals in Town of Leon

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Top-rated vacation rentals in Town of Leon

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Guest favorite

The living area features wooden beams and a cozy layout. A comfortable sofa and armchair surround a wooden coffee table. A pellet stove adds warmth, while a television is mounted on the wall. Windows provide natural light, and nearby furniture includes a dining table and chairs.

Cabin in Redgranite

4.88 out of 5 average rating, 60 reviews

Wooded Tranquil Getaway

This Veteran owned charming cabin is simply adorable! Situated directly across the street from the breathtaking Pearl Lake, it offers stunning views and a serene atmosphere. For the adventurous family bring your water toys so you can enjoy the surrounding lakes and boat, waterski, swim or hike. A quick 12 minute drive to Nordic Mountain, perfect for winter skiing or tubing! Located in central Wisconsin, you'll have easy access to supper clubs, golf courses, public hunting and fishing grounds.

Guest favorite

A welcoming living area features a large circular table in the center, surrounded by comfortable seating. Natural light streams through multiple windows, highlighting the wooden accents and beams in the ceiling. A bookshelf displays various items, adding warmth to the space.

Cottage in Neshkoro

4.95 out of 5 average rating, 211 reviews

Nostalgic Lakehouse with Ferry Pontoon & Hot Tub

This thoughtfully restored 1960s cottage sits on peaceful Spring Lake: perfect for swimming, fishing, and creating nostalgic memories lake with your family. Outside you'll enjoy a beautiful private backyard with a hot tub, paddle/solar-powered pontoon boat, yard games, fire pit, fishing poles, and dock. Inside you'll make lifelong nostalgic memories with the huge selection of 1980/90s video games, Goosebumps books, board games & VHS films. Centrally located in an activity-filled area of WI!

Top guest favorite

The exterior of the barn features a sleek black facade with white trim, including multiple windows that allow natural light to enter. A wooden fence provides privacy, and the entrance is marked by a simple white door. Lush greenery surrounds the barn, enhancing its rustic charm.

Cabin in Princeton

4.99 out of 5 average rating, 111 reviews

Private Riverfront, Converted Barn *EV Charger*

Fox River Barn is located in a picturesque setting with stunning views of the Fox River in Princeton, WI. This 1940s barn has been lovingly converted into a comfortable living space with modern features and amenities, making it the perfect retreat for a romantic getaway or a peaceful escape from the city. Inside, the bones of the barn are present. From beams and rafters on the main level to the tall, gable barn ceiling. Just imagine all the different ways the barn had been used over time.

Guest favorite

The A-frame cabin is surrounded by mature pines, featuring a spacious lawn with a fire pit and several blue adirondack chairs. A charcoal grill is visible, and the deck includes umbrellas for shade, offering an inviting area for outdoor relaxation.

Cabin in Princeton

4.97 out of 5 average rating, 227 reviews

A-frame in the Pines

"Up North" cabin decor with modern amenities. Cute A-frame cabin nestled amongst mature red & white pines. Outside space to run & play or relax by the campfire or fireplace inside. Chargrill available. Bring your own charcoal. Living room with TV, dining area, kitchen & pantry, bathroom, & bedroom with a queen size bed on main level. The "loft" upstairs has 2 bedrooms, 1 with 2 twin beds , & the other space with a queen size bed and a reading area that opens up to your own private balcony.

Top guest favorite

A spacious deck is set under a large blue canopy, providing shade over a wooden dining table surrounded by six woven chairs. The deck overlooks a serene lake, framed by lush greenery and trees.

Home in Waupaca

4.9 out of 5 average rating, 146 reviews

Between two Lakes Beautiful 2-Bedroom Cottage!

Welcome to Two Lakes cottage in between the towns of Waupaca and King. This beautiful two-bedroom cottage sleeps seven and offers seclusion and quiet but is still only 5 minutes from the hustle and bustle of Downtown Waupaca and the nightlife of the Chain O’ Lakes. If it's a relaxing vacation you're looking to enjoy. Relax on our large deck and enjoy the view of the lake behind the house.If it's drinks and live music that toots your horn, this cottage is perfect for you! 900 sq ft total.

Top guest favorite

Cabin in Cascade

5 out of 5 average rating, 174 reviews

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

Top guest favorite

The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.

Cabin in New London

4.99 out of 5 average rating, 100 reviews

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Top guest favorite

The cabin features a welcoming front porch with a swing and a picnic table. A charcoal grill is positioned nearby, set against a backdrop of lush greenery. The exterior is adorned with wood siding and large windows, creating a pleasant connection with the surrounding nature.

Cabin in Hancock

4.96 out of 5 average rating, 223 reviews

Peaceful Cabin in the Woods

🌲 Welcome to Your Secluded Cabin Getaway 🌲 Escape the city and enjoy a peaceful retreat on 5 private acres in Hancock, Wisconsin, just minutes from downtown Wautoma. Surrounded by woods, our cabin offers the perfect setting to: Sip your morning coffee or an evening glass of wine on the front porch swing ☕🍷 Relax around the crackling fire pit 🔥, roasting marshmallows, and enjoying the stars ✨ This cabin is designed for comfort, relaxation, and creating unforgettable memories.

Guest favorite

A cozy seating area showcases a wood-burning stove set against a rustic brick wall. A warm plaid blanket is draped over a plush sofa, while a small side table holds a book and a glass of wine. Soft light filters through large windows, highlighting the inviting atmosphere.

Cottage in Neshkoro

4.95 out of 5 average rating, 146 reviews

Pet Friendly Antique Schoolhouse with Fenced Yard

Pond Lily is truly a unique stay; a historic schoolhouse among tranquil surroundings. Beautiful traditional craftsmanship meets all the comforts of a modern home. Pet friendly with a fenced yard. A well-stocked kitchen makes for easy home-cooked meals. The layout is ideal for small groups looking to enjoy a peaceful getaway. Snuggle up by the wood-burning fireplace in the cold months or enjoy the firepit in the warm weather. For the outdoorsman, public lands are 5 minutes away.

Top guest favorite

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

4.99 out of 5 average rating, 286 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Guest favorite

An outdoor fire pit area is surrounded by lawn chairs and hanging hammocks, offering a relaxing atmosphere by the lake. The calm water is visible in the background, complemented by lush greenery and a nearby dock with boats.

Home in Wautoma

4.96 out of 5 average rating, 137 reviews

Crisp Air, Cozy Fires & Lakefront Flair

Nestled by the lake, our cozy summer retreat sleeps 7 and offers sunny views, a hot tub, and an outdoor firepit with firewood. The pier is in for the season, and a pontoon boat is included May–September (weather permitting). Enjoy 2 kayaks, 2 paddleboards, & a pedal boat for fun on the water. With modern interiors and relaxing outdoor spaces, it’s the perfect place to unwind and enjoy lake life.

Top guest favorite

A modern kitchen space features a central island with barstools, accompanied by pendant lighting overhead. Nearby, a cozy living area is visible with a sectional sofa and artwork adorning the walls. Natural light fills the room through multiple windows, enhancing the inviting atmosphere.

Apartment in Waupaca

4.97 out of 5 average rating, 186 reviews

Contemporary Retreat | Steps from Chain O' Lakes

Mid-century modern meets old-fashioned hospitality. A newly (and lovingly) remodeled duplex in the lakeside hamlet of King. Just steps from the pristine Chain O' Lakes, restaurants, boat-rentals, bars, shopping and more. Perfect for cottage overflow, an extended executive assignment, or road-trippers passing through Central Wisconsin to all points beyond.