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
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, 146 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
4.92 out of 5 average rating, 288 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 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, 207 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.

Guest favourite
Place to stay in Saint Croix Falls
4.94 out of 5 average rating, 442 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 Grantsburg
4.96 out of 5 average rating, 780 reviews

Quiet Seclusion at Trade River Retreat Cabin

Remote, tranquil, quiet and exceedingly private getaway right on the banks of a protected river, only 1.5 hours from the Twin Cities! Even the beautiful drive there is relaxing. Enter a world of peace and calm deep in the woods. Make delicious meals in a well-stocked modern high-end kitchen, play in the river, relax in the sauna or enjoy a bonfire. This is not your typical cabin but a spiritual eco-oasis with a unique eclectic blend of modern, rustic, Native American and Japanese aesthetic.

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
4.98 out of 5 average rating, 106 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.

Top guest favourite
A rustic cabin exterior is framed by lush greenery and a wooden trellis. Comfortable seating arrangements, including wicker chairs, are present on a spacious deck, inviting relaxation. Large glass doors reveal the interior and provide a connection to nature and the tranquil setting by the lake.
Cabin in Menomonie
5 out of 5 average rating, 59 reviews

Echo Point | Historic Lakeside Cabin

Echo Point's guest cabin is a unique and tranquil getaway perched on the edge of the water with a grand view of Tainter Lake, about an hour east of Minneapolis/St. Paul, MN. This renovated cabin - originally built in the 1950's atop a boathouse - provides guests the feeling of being in the trees overlooking the lake. It is the perfect getaway to unwind in nature. Please note: We do not allow parties or pets, and the property isn't suitable for those with mobility challenges (stairs)

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, 108 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**

Top guest favourite
Cabin in Webster
4.97 out of 5 average rating, 231 reviews

Riverside Retreat- A small cabin for big memories!

Renovated cabin nestled high in the pines overlooking the river. Kick back and relax in this calm, stylish space where the river views will take your breath away. We have a great selection of games, books and movies to snuggle up with in front of our warm fireplace. Bring your snowmobiles, ATVs and ice fishing gear as we are close to the Gandy Dancer Trails and our beautiful river flows to two lakes for great fishing - end at our bonfire pit to roast S'mores and swap stories!

Guest favourite
Home in Chetek
4.8 out of 5 average rating, 5 reviews

Pike Retreat at Pokegama - 2BR Lakefront w/ Dock

Pike Retreat: 160ft Private Shoreline w/ Dock & Seclusion Experience the ultimate private escape. Pike Retreat - 160ft of private shoreline on Pokegama Lake—the rarest luxury on the Chetek Chain: Total Seclusion. The Vibe: High-end Northwoods modern. Designer finishes meet peace and quiet. Top Features: - 160' private frontage & dock - Premium linens & furniture - Locally managed by family owners Perfect for families seeking a quiet retreat. Book a slice of paradise!

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.

Guest favourite
Home in Cumberland
5 out of 5 average rating, 12 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

Popular amenities for Hillsdale holiday rentals

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