Holiday rentals 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
A modern cabin is seen from across the lilypad-filled bay, featuring large windows and a deck. A small dock with two red Adirondack chairs invites relaxation, surrounded by lush greenery and a winding path leading up to the cabin.
Cabin in Amery
5 out of 5 average rating, 139 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

Superhost
A serene lakeside view during sunset is captured, with vibrant orange and purple hues reflected in the calm water. A wooden dock extends into the lake, bordered by pine trees. The tranquil atmosphere invites relaxation and connection with nature.
Home in Chetek
4.89 out of 5 average rating, 142 reviews

Amazing views, remodeled basement, pontoon to rent

Come experience the great Northern Wisconsin. We are located 5 miles from town, sitting on a dead-end road, with public access <1 minute away. It is a quiet place perfect for retreats, family gatherings, romantic getaways, or simply a vacation with friends/family. Several restaurants and bars either a boat or car ride away. This four-season home is the perfect location whether you are looking for a quiet weekend escape, or to fill your weekend with outdoor activities. *PONTOON FOR RENT ON-SITE*

Top guest favourite
Tiny home in Saint Croix Falls
4.92 out of 5 average rating, 272 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
A wooden cabin with a sloped roof is set amidst lush greenery. Steps lead down from a small screened porch, surrounded by trees. The inviting exterior of the cabin complements the natural surroundings, providing a picturesque view of the adjacent lake.
Cabin in Comstock
4.95 out of 5 average rating, 215 reviews

Lakefront Lodge w/ Hot Tub, Sauna, Fireplace

Visit our updated, cedar lined cabin on Long lake! The main level has a kitchen, living area, dining area, 1 bedroom and bathroom. The upstairs has 2 bedrooms. The downstairs "game room" with darts, a foosball table, and a big screen TV. Enjoy the hot tub overlooking Long lake! Relax and detoxify in the brand new infrared sauna. Feel like you are sitting in a tree house while you enjoy the screen porch overlooking the serene lake. Cozy up by the real wood fireplace. Pets welcome for a $90 fee.

Top guest favourite
Cabin in Birchwood
4.98 out of 5 average rating, 106 reviews

The Bunk House Lakefront Cabin in Birchwood, Wi

Newly remodeled Lakeside Cabin on beautiful, spring fed, Spider Lake chain. The cabin is 4 season with 3 bedrooms and 2 bathrooms. Enjoy brand new stainless steel Fridgaire Gallery appliances with a view of the lake from every window! Feel free to use the 2 person Canoe and three childrens Kayaks to explore the crystal clear chain of 6 Lakes. 75% of the lake is Ntl. Forest making it one of the most peaceful and quite lakes around. Great Crappie, Blue Gill, Bass and Northern fishing. ENJOY!

Top guest favourite
Cabin in Amery
5 out of 5 average rating, 172 reviews

On River’s Bend | Apple River | Hiking | Camp Fire

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
The open living area features large floor-to-ceiling windows, allowing natural light to fill the space. A modern kitchen with stainless steel appliances is complemented by wooden cabinetry. Comfortable seating arrangements include a sleek sofa and a chair, arranged around a glass coffee table.
Cabin in Frederic
5 out of 5 average rating, 287 reviews

Nordlys Lodging Co. - MetalLark Tower

Perched high among the trees with breathtaking views of the hidden lake and wildflower meadows, MetalLark Tower is the perfect getaway. This two-story, 800 sq.ft. cabin has one king bed, one hide-away bunk bed, and one bathroom. We put the living area high up on the second floor to give our guests a bird’s eye view. Floor to ceiling glass brings the outdoors inside, and each season brings its own unique perspective. Staying in MetalLark tower is truly a one-of-a-kind experience.

Top guest favourite
The exterior of a single-story home is shown, featuring a white facade with red trim. Several small windows allow natural light, while a grassy area surrounds the house. A concrete path leads to the entrance, indicating accessibility and connection to the outdoor space.
Home in Chetek
4.92 out of 5 average rating, 155 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
4.97 out of 5 average rating, 177 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 area features vaulted wood-paneled ceilings with a fan and large windows offering views of the lake. A combination of comfortable seating is arranged around a coffee table, with a television positioned near a gas fireplace. A dining area is visible in the background.
Cabin in Chetek
4.91 out of 5 average rating, 143 reviews

Huber Cottage - Lakefront Cabin w/Dock and Beach

Prime location on the main part of Lake Chetek, the most popular lake in the Chetek chain,. Enjoy the convenience of shops and restaurants within walking distance without losing the true "cabin on the lake" experience! Enjoy access to the public beach next door or take your boat for a cruise through the famous Chetek chain of lakes; tie up your boat on our private dock when you're ready to hunker in for the night. An outdoor firepit is also available for s'more makin'!

Top guest favourite
An open concept area features a vaulted ceiling with a large archway adorned with string lights. A cozy kitchenette is visible, along with rustic wooden walls and charming decor creating a warm space. An inviting atmosphere is enhanced by the soft illumination throughout.
Cottage in Rice Lake
4.99 out of 5 average rating, 139 reviews

Stonehaven Cottages The Turtle cottage

Slow and steady wins the race! We are tickled to introduce our second cottage "The Turtle" here at Stonehaven Cottages on Tuscobia Lake, LLC. We put in a large archway in the vaulted ceiling to give it a look and feel of being inside a turtle shell. This cozy cottage has an open concept with full kitchen, one small bedroom and a queen sofa sleeper. It also has a spectacular view of Tuscobia Lake! When life gets too busy, come and slow down a bit at "The Turtle"!

Guest favourite
The glass house exterior features a wooden deck adorned with decorative lanterns and a vibrant area rug. Inside, a spacious bed and a cozy sofa are visible, separated by sheer curtains. A private hot tub is positioned nearby, surrounded by nature.
Dome in Afton
4.87 out of 5 average rating, 409 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.

Popular amenities for Hillsdale holiday rentals

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