Holiday houses in Hillsdale

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Top-rated holiday rentals in Hillsdale

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

The great room features a tall ceiling with a modern chandelier overhead. A cozy leather Chesterfield sofa surrounds a rustic coffee table. Large windows provide views of the lake, framed by warm-toned drapes. A fireplace adds warmth, complemented by vintage decor elements on the walls.

Cabin in Amery

5 out of 5 average rating, 148 reviews

Lakefront Cabin | Amazing Views | Kayaks Wildlife

Welcome to The Backwater, a newly built architect designed year-round getaway on Pike Lake in Amery, WI. Nestled in the back of a quiet, lilypad-filled bay teeming with wildlife, our cabin is the perfect destination for guests who appreciate original design and crave a unique experience. Our amenities are luxurious, but our attitude is chill inside our comfy, creative digs full of nostalgic, vintage vibes. Come stay and play on the bay while enjoying Polk Co.! Follow along @thebackwater_wi on IG

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Top Guest favourite

A cozy tiny home is illuminated at night, revealing warm light from its windows. A stone pathway leads to an inviting front deck surrounded by greenery. Nearby, a decorative lantern can be seen in the foreground, enhancing the serene ambiance.

Tiny home in Saint Croix Falls

4.92 out of 5 average rating, 290 reviews

Wolf Creek Luxury Eco-Tiny Home on the Ridge

Experience our custom-built eco-friendly tiny home perched on the top of the ridge above the majestic St Croix River Valley. Enjoy expansive views from the deck, loft or many windows looking over the valley. Enjoy our private barrel-sauna, fire-pit, gas grill, pond with canoes and kayak or Wolf Creek with a private crystal-clear swimming hole! Or just chill on the ridge watching the many birds and wildlife. Just over an hour drive from the Twin Cities, a romantic and memorable stay awaits you!

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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, 210 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.

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Top Guest favourite

Place to stay in Saint Croix Falls

4.94 out of 5 average rating, 448 reviews

The Wissahickon Inn - The Cozy Cabin In The Woods

You'll love our cabin in the woods! Once a historic mercantile, the Wissahickon Cabin has been transformed into a cozy cabin for 2 - 4 guests. The cabin is situated in the forest and visible from the Gandy Dancer Trail. The front porch boasts an access path directly to the popular Woolly Bike Trail. Our cabin is secluded in the woods, but it's less than a 5-minute drive to downtown St Croix Falls, Interstate Park, dining, shopping, and entertainment. Enjoy a peaceful getaway in the north woods!

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Guest favourite

A spacious living area features warm knotty pine walls and a high ceiling adorned with large windows. A stone fireplace is centrally located, surrounded by comfortable seating and wood cabinetry. Sunlight filters through the windows, illuminating the inviting space.

Cabin in Cameron

4.93 out of 5 average rating, 54 reviews

Little Cottage On Prairie

Little Cottage on Prairie meant for relaxation! Located on Prairie Lake & Lake Chetek. Launch your boat off Wolf's Den Resort or public launch. Fish Panfish, Bass, Northern, Walleye right off cabin dock. Prairie Lake water quality is great. Knotty pine interior is tastefully decorated. Relax in front of wood burning fireplace after ice fishing or snowmobiling. Stroll down to the lake. Use kayaks of boat dock. Stargaze, roast S'mores at lake-side fire pit or the fire pit closer to the cabin.

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Top Guest favourite

A modern cabin is nestled among tall trees, showcasing a blend of natural wood tones and large windows that invite natural light. The surrounding landscape features green grass and a gently sloped area leading to the tree line, enhancing the cabin’s secluded atmosphere.

Cabin in Chetek

4.97 out of 5 average rating, 110 reviews

Newly Updated Cozy Lakefront Cabin On Private Lake

Tranquil cozy dog friendly cabin nestled in the woods on a peaceful private lake. True northwoods rustic feel for a romantic couples trip or escape from the city with family or friends. New plush bed & comfy recliners. 58" 4K smart TV & fiber internet. Fully stocked kitchen w/new SS appliances. Gas stove, microwave, fridge w/filtered water & ice dispenser, dishwasher, Keurig w/pods included. Abundant wildlife! No gas motors allowed on lake but pedal & row boat free to use at your own risk.

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Guest favourite

An A-frame cabin is nestled among trees, with warm light glowing from its windows. Two bright orange chairs are positioned around a fire pit made of stones, providing a cozy gathering spot just outside the cabin. A spacious deck extends from the entrance.

Cabin in Colfax

4.97 out of 5 average rating, 112 reviews

A-Frame DGP | a cozy riverside cabin ~1hr from MSP

This retro, but modern A-frame cabin is tucked neatly into a wooded hillside, overlooking a peaceful river, near Menomonie, WI. ~1 hour from the Twin Cities. The space has been revived by lovers of architecture, design and the great outdoors as a quiet getaway for couples or friends looking to slow down and reconnect. Note: we do not allow parties or pets, and the property isn't suitable for children or those with mobility challenges **please read entire description before booking**

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Top Guest favourite

An outdoor area is visible with a large circular firepit surrounded by gravel. A covered porch is seen with several seating options, including two rocking chairs. The cabin's green exterior and weathered stone accents provide a rustic setting against a backdrop of trees.

Cabin in Wheeler

4.97 out of 5 average rating, 185 reviews

Kamshire Valley (Main Cabin)

25 minutes from Menomonie (UW-Stout), 45 minutes to Eau Claire, 1 hr 15 minutes to MN. Kamshire Valley's Main Cabin offers an abundance of wildlife viewing, an inviting large brick patio and firepit, miles of trails for snowshoeing, hiking and cross-country skiing. Has 1 bedroom with Queen bed; If you need more rooms we have 2 additional rustic cabins (air, heat-no bathroom) that are available for additional $50/ cabin/night. The best nature has to offer, bring your camera!

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Top Guest favourite

The exterior of the cottage features rustic dark wood siding and a welcoming entry door. A well-maintained yard showcases green grass and a small flower bed. A fenced area provides privacy, and a patio space with seating is visible, ideal for outdoor relaxation.

Home in Chetek

4.98 out of 5 average rating, 84 reviews

Maple Cottage

Come and relax at the Maple Cottage located just a few blocks from beautiful Lake Chetek. Conveniently located within walking distance to some of Barron County's best coffee shops, bakeries and ice cream. This small town has many shops of interest including antique, boutique and sporting stores - not to mention all the favorite places to eat! Cozy up on the couch in front of the fireplace, or enjoy the hammock lounge under the maple in the private back yard.

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Top Guest favourite

A view of the cabin exterior features a wooden structure with a sloped roof and large overhangs. The warm glow of interior lighting is visible through expansive glass windows. Surrounding trees create a natural backdrop, enhancing the serene setting.

Cabin in Frederic

5 out of 5 average rating, 210 reviews

Nordlys Lodging Co. - LongHouse

Perched high on a bluff over the hidden lake, LongHouse is the perfect getaway. This one-story, 1,200 sq.ft. cabin has one king bedroom, one queen bedroom, and two bathrooms. Floor to ceiling glass brings the outdoors inside, and each season brings its own unique perspective. Traverse the bridge over a dry creek bed and enjoy water views from a large screen porch. Staying in LongHouse is truly a one-of-a-kind experience.

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Guest favourite

Home in Cumberland

5 out of 5 average rating, 13 reviews

Lake Farmhouse Getaway | Game Room | Pet Friendly

The lake is 100 yards away. The arcade is upstairs. The fireplace is already on. Welcome to the Grenquist Farmhouse — Scandinavian lakeside retreat with kayaks, paddleboard, Marvel vs. Capcom arcade, vintage 1970s pinball & loft game room. Sound machines & blackout curtains in every bedroom. Pets welcome. Full kitchen, in-unit washer/dryer & 300+ mbps WiFi. 3BR/2BA sleeps 4. Cumberland, WI — 90 min from Twin Cities

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Guest favourite

A spacious bedroom is highlighted by a comfortable king-sized bed adorned with colorful pillows. A ledge stone fireplace is situated near large windows, allowing natural light to fill the room. A cozy seating area with a small table is also present, enhancing the overall ambiance.

Barn in Hillsdale

4.96 out of 5 average rating, 26 reviews

The Loft Suite @ The Granary

The Loft Suite @The Granary is an ultimate retreat into luxury amid the beautiful views of the grounds. Enjoy the ultra-comfortable king-sized bed, a ledge stone fireplace, and a relaxing rainfall shower. The suite includes an atrium with a kitchenette adjacent to a main king room through spacious French doors. Many unique touches of elegant country charm. Sleeps 2.

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