Cottage holiday rentals in Wisconsin

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Top-rated cottage rentals in Wisconsin

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Top Guest favourite
A quaint cottage is illuminated at night, showcasing its rustic wooden exterior and sloped roof. Soft lighting highlights the entrance, leading up a set of wooden steps surrounded by vibrant foliage and stone landscaping, against a backdrop of a deep blue twilight sky.
Cottage in Glenwood City
4.96 out of 5 average rating, 206 reviews

Cozy Farmstead Cottage Getaway

The cottage is located on our 80 acre farmstead in the bucolic rolling hills of Western Wisconsin just over an hour from the Twin Cities. Relax, create, or dream in this peaceful setting. Cherish time with loved ones. Hike along the creek, woodlands and fields. Enjoy the plentiful birds and wildlife. Bring your bike in the summer, and snow shoes in the winter. Cozy up to the wood stove with a hot beverage. Work remotely with our high speed WiFi. We welcome up to two dogs for an additional fee.

Top Guest favourite
The logo for Witt's End Weekend Retreat features a stylized silhouette of a cottage surrounded by tall pine trees and a rising sun. The design incorporates earthy orange and green hues, conveying a sense of tranquility amidst nature, with the text prominently displayed.
Cottage in Mountain
4.98 out of 5 average rating, 214 reviews

Witt's End, a relaxing Northwoods Lakeside Retreat

Our property on Little Gillett Lake is a special place. The cottage is new, but exudes the charm and character of classic Northwoods Americana. The clear, beautiful lake allows access to Big Gillett Lake and a tributary of the Oconto River by paddle. The Nicolet National Forest offers trails while nearby larger lakes provide beaches and access for motor boats. Swim, paddle, fish, snowshoe, ATV, snowmobile, hike, eat, chill... come enjoy some worry free relaxation or step away for an adventure!

Top Guest favourite
A spacious living area showcases high vaulted ceilings with exposed wooden beams. Large windows allow natural light to fill the space, highlighting the comfortable seating area and dining table set for a meal. A staircase leads to an upper loft area, enhancing the openness of the layout.
Cottage in Eastman
4.97 out of 5 average rating, 165 reviews

Summer special-book 5 nights-6th night free

Newly Constructed, (2018) Family Owned Loft House in a quiet, relaxing, 2 acre country setting overlooking the Mississippi River! 2500 sq. ft. Just 4 miles from Gatherings on the Ridge, 20 minutes from Historic Downtown Prairie Du Chien and a short jaunt to the river. Sleeps 8-10, master bedroom with a queen, 2 queens & queen sofa sleeper in loft, queen in basement , 2 baths, master bath has jetted tub, full kitchen (pots, pans, dishes, toaster, keurig, coffee pot, coffee, waffle iron, etc.)

Guest favourite
Cottage in Princeton
4.94 out of 5 average rating, 247 reviews

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Top Guest favourite
A serene view of a two-story cottage situated next to a reflective creek, surrounded by lush greenery. The building features large windows that offer a glimpse into the inviting interior. The clear blue sky and sun-dappled trees enhance the peaceful atmosphere.
Cottage in Westby
4.99 out of 5 average rating, 155 reviews

Timber Creek Retreat

Get away for a restful stay at this scenic hidden gem of Vernon County. Timber Coulee Creek, a Class 1 trout stream, ripples right through the backyard. You will enjoy watching deer and turkey as they amble through the property. Bald eagles soar overhead and fish jump in the stream. Listen to the gurgle of the water flowing over the rocks and the music of the birds. Try your hand at fly fishing. Sit around the fire pit, roast marshmallows, watch the flames dance and the stars come out.

Guest favourite
Cottage in Neshkoro
4.91 out of 5 average rating, 259 reviews

Nostalgic Lakehouse with Pontoon, HotTub & VHS

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, pedal-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 favourite
A cozy cottage is framed by surrounding trees, featuring a stone fire pit in front. Large glass doors illuminate the interior from within, while wooden siding adds a natural touch. Two outdoor chairs are positioned nearby, offering a serene view of the landscape.
Cottage in Sturgeon Bay
4.93 out of 5 average rating, 234 reviews

Peace of Beach, 4 season waterfront cottage

Beautiful 4 season, private 2 bedroom Knotty Pine Cottage located on the shores of Lake Michigan just 10 yards away from water in Sturgeon Bay, WI. 2 BR/1 bath cottage with beautiful stone, wood burning fireplace. A fully equipped kitchen with high bar dining which seats 8. Lots of living space with leather sectional and full size hide-away sofa sleeps 2, Main Guest Room 1 w/ queen log bed and Guest Room 2 with full size log bunk beds, Large screen tv, wifi and panoramic lake view.

Top Guest favourite
An open second-floor area is depicted, showcasing a sleek wooden bookshelf filled with books and decorative items. A spacious bed is positioned near a window, while a cozy seating area with black leather sofas invites relaxation. Natural light streams through the windows, highlighting the wood flooring.
Cottage in Neshkoro
4.96 out of 5 average rating, 174 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 favourite
A spacious outdoor area features a circular seating arrangement of black Adirondack chairs surrounding a stone fire pit. The yard is lush and green, leading to views of the water and distant trees under a partly cloudy sky.
Cottage in Sturgeon Bay
4.99 out of 5 average rating, 145 reviews

Waterfront Cottage · Kayaks · Firepit · Sun Porch

Sawyer Harbor Retreat is a private waterfront cottage tucked on the harbor, with a big open yard running down to the water and quiet that's hard to find. Kayak and chase sunsets in summer; come fall, it's golden mornings on the water, a round at Idlewild, and color hikes at Potawatomi State Park — all minutes from Sturgeon Bay. With 3 bedrooms, 2 full baths, and room for 10, it's an easy fit for families, couples, and friends after a relaxed Door County escape.

Top Guest favourite
Cottage in Sister Bay
5 out of 5 average rating, 241 reviews

2 Bed A-Frame, Fire Pit, Coffee Bar - Sister Bay

Trade the hustle and bustle for peace and quiet at our cozy retreat, just 5 minutes from the heart of Sister Bay. Tucked away on 1.6 acres of serene woods filled with beautiful beech trees, the cottage is your perfect getaway spot. Kick back on the spacious front deck, unwind on the screened-in porch, and soak in the natural beauty all around. Inside, mid-century modern vibes meet cozy comforts, with everything you need for a relaxing, stress-free stay.

Superhost
A wooden deck is illuminated by string lights, featuring a hot tub and outdoor seating. The cottage, with a blue door and an umbrella, is adjacent to a sauna. A warm ambiance is created as twilight sets in, highlighting the inviting outdoor spaces.
Cottage in Townsend
4.85 out of 5 average rating, 99 reviews

Waters Edge Cottage: Cozy. Sauna. Hot Tub

SAUNA, HOT TUB, STARS. The name says it all. Waters Edge Cottage, located right on the shore of beautiful full recreation Pickerel Lake! Step off the deck and into the hot tub or sauna right on the shore. Waters Edge Cottage has 1 Bedroom with a Queen Bed plus a loft with 3 twin beds, fully stocked kitchen & full bath. Pontoon Boat available to rent! Golf, ATV, Wineries, Hiking, Biking, Swimming, fishing and more! Come enjoy Waters Edge

Top Guest favourite
The image captures a vibrant sunset over the lake, with a palette of deep oranges, purples, and pinks reflecting off the tranquil water. The silhouette of trees along the horizon enhances the serene ambiance of the natural landscape.
Cottage in Elcho
5 out of 5 average rating, 112 reviews

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!

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