Holiday rentals in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Top guest favourite
A field stone fireplace serves as a central feature against walls constructed with natural birch logs. A stone mantel provides a surface for decorative items and creates a cozy focal point. Soft lighting from above enhances the inviting atmosphere of the room.
Cottage in Rice Lake
4.98 out of 5 average rating, 127 reviews

Stonehaven - The Birchview Suite Lower Level

The Birchview Suite lower level duplex is totally closed off from guests in upper level. It features two french doors that lead out to the large flagstone patio area, which is the main entrance. There's a full kitchen for you to prepare meals. We have a private dock 1/4 mile from the cottage and offer complementary use of kayaks, row boats, and canoes! We also have a pontoon for rent. Plenty of hiking and biking opportunities can be found on and off the resort. State Trails are also nearby.

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, 137 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

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
4.91 out of 5 average rating, 263 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!

Top guest favourite
An outdoor entertaining area is highlighted, featuring a gazebo with a grill, a fire pit, and seating arrangements. Three kayaks are stored nearby, and the lawn is surrounded by lush greenery. The cottage has an awning above the deck, providing shade.
Cottage in Chetek
4.93 out of 5 average rating, 107 reviews

Cozy Cottage on the Chetek Chain of Lakes.

The Ager cottage is located on an island in the Chetek Chain of Lakes. 1 bedroom with queen bed, kitchen, futon, garage, dock. Causeway to the island. Nearby beach, airport, dog park, 2 miles to downtown Chetek. Boating, fishing, hiking, skiing, snowmobiling. Secluded cabin, sleeps 4 guests, but you have to like each other a lot. Wildlife viewing. Bald eagles, deer, otters, heron, wood ducks, muskrat, rabbits, turtles, frogs. Three kayaks, a Grumman canoe and two bicycles are available.

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, 205 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
Place to stay in Saint Croix Falls
4.95 out of 5 average rating, 411 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!

Top guest favourite
Cabin in Amery
5 out of 5 average rating, 169 reviews

On River’s Bend | Apple River | Hiking | Campfire

Perched high on the banks of the Apple River, this timber-framed cabin offers spectacular views of the river and wildlife. We’ve spotted bald eagles, deer, ducks, geese, great blue heron, golden eagle, fox, beaver, bear and wild turkey from the comfort of the cabin. One hour from the Twin Cities, it’s the perfect cabin getaway for couples, friends, and families. Located on private acreage in Amery, WI you will be near rivers, lakes, hiking trails and all that Northern Wisconsin has to offer.

Top guest favourite
A single-story house is shown, featuring a large front window framed by plants and a well-kept lawn. The exterior wall is white with red trim, and the setting includes trees in the background for a natural feel.
Home in Chetek
4.91 out of 5 average rating, 151 reviews

EDBD Cozy Home

Lake across the road within view, walking distance to public beach, new Gotham sports complex and boat landing, on public snowmobile and ATV trail. Two-bedroom home all on one level with very comfortable beds. Small cabin feel within walking distance to downtown. Massage chair and 2 kayaks available for your use. High Speed Internet that can be used for working remote. Enjoy a peaceful night around a campfire or sitting next to a tiki bar. TV available in each room with Roku.

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
4.98 out of 5 average rating, 171 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!

Guest favourite
The living room features a combination of handcrafted log walls and a large stone fireplace. Two cozy chairs and a lamp invite relaxation, while a wooden table sits nearby. Natural light filters through the glass door, leading to an external porch, with shelves holding various games.
Cabin in Sarona
4.92 out of 5 average rating, 286 reviews

Hunt Hill's Rustic Log Cabin

Welcome to Hunt Hill Nature Center! We are a public, non-profit learning center and nature sanctuary. Our historic Log Cabin is nearly a century old and offers a peaceful retreat in the woods. All the furniture was updated in 2018. The Log Cabin is located just outside of the main camp, settled on top of a hill overlooking pristine forest habitat. Nearby towns offer additional entertainment or relax in our quiet setting while reading a good book in front of the stone fireplace.

Superhost
A glass house reflects natural surroundings, enclosed by trees and sunlight. The interior features a spacious bed draped in white linens, with cozy seating visible nearby. A wooden deck extends outwards, complemented by outdoor furniture and decorative lanterns.
Dome in Afton
4.87 out of 5 average rating, 402 reviews

Star Gazing Glass House 4 Season with Hot Tub

This glass house has a mini split offering both heat and air conditioning. There is something truly magical about being submersed in nature. Watching beautiful snowflakes cascade around its walls, snuggled under heated blankets while star gazing. Rainstorms have a new meaning, sunsets and sunrises become a life-changing experience. This is a photographer's dream, a romantic getaway, or the perfect place to reconnect with yourself. Private hot tub and fire pit.

Guest favourite
A wooden picnic table with attached benches is situated on a grassy area, surrounded by mulch. Two blue chairs are positioned nearby. A grill is partially visible to the right. The lake is seen in the background, with a dock extending into the water.
Cabin in Cameron
4.93 out of 5 average rating, 125 reviews

Cabin 2 - Northwoods themed 1 BR, lakefront cabin.

Relax in this cozy lakefront cabin. This north woods themed cabin is perfect for a couple looking for a weekend or week-long getaway. The cabin includes a fully stocked kitchen, a 3/4 bathroom and a separate living area. Relax outside on the attached, covered deck or walk 30 feet to your own dock. Bring your boat and enjoy all that the Chetek Chain of Lakes has to offer. Or rent one of our pontoons by the hour or by the day.

Popular amenities for Hillsdale holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Barron County
  5. Hillsdale