Vacation rentals in Hillsdale

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Top-rated vacation rentals in Hillsdale

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Top guest favorite
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, 275 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 favorite
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.

Guest favorite
A modern single-story home is set amidst lush greenery, featuring a welcoming entrance with wooden steps leading to a porch. The exterior is clad in dark gray siding, complemented by large windows that provide natural light, and a manicured garden adding a touch of color.
Cabin in Frederic
4.93 out of 5 average rating, 270 reviews

Up North Retreat: Peaceful & Relaxing But Modern!

Your private getaway up North! Full renovation throughout makes this a tranquil and relaxing, yet modern escape. Enjoy a warm bath in the jacuzzi tub, grab some coffee in the gorgeous custom kitchen with SS appliances, and cozy up to a movie in front of the electric fireplace! Two full bedrooms and baths for amazing privacy. Explore the local scenery by day and Sit around the bonfire by night! You won't find anything this peaceful without sacrificing the modern essentials. Fiber internet, too!

Top guest favorite
The kitchen area features wooden cabinetry and modern appliances, including a refrigerator and microwave. A dining table with wooden chairs is visible, along with a cozy seating arrangement. The walls are painted in a calming green, contributing to a welcoming and functional space.
Apartment in Elk Mound
4.95 out of 5 average rating, 495 reviews

Oak Hill Retreat

Country location, peaceful and quiet. Apartment above detached garage, full kitchen, small deck and private stairway with beautiful view of the surrounding trees. Easily accessible, 3 miles from I-94 and St. Hwy. 29, 1/2 way between the university cities of Eau Claire and Menomonie, 1 1/4 hours from St. Paul/Minneapolis. There is a growing art and music scene, with multiple music festivals, etc. The area also has fine restaurants, theaters, parks, and historical sites. Come to be restored.

Top guest favorite
Cabin in Grantsburg
4.96 out of 5 average rating, 770 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 favorite
A spacious living area features large, triangular windows that frame serene outdoor views. A wood-stove stands at the center, surrounded by natural materials. Comfortable seating includes a plush sofa and sleek lounge chairs. Light hardwood floors complement the cozy atmosphere, illuminated by natural light.
Cabin in Comstock
5 out of 5 average rating, 31 reviews

Snowfall Escapes - Lakefront Cabin w/ Loft & Bar

Lakefront cabin on quiet North Pipe Lake—near Turtle Lake & Cumberland. Queen & full beds in loft + queen murphy & twin roll-away on lower level, where a glass garage door opens lakeside from a bar/lounge. Main level has wood-stove & gathering kitchen. Enjoy a panoramic lake-view deck & screened-in porch. Fish off the dock, paddle to the public beach on Pipe Lake, or load your boat at the public landing and dock it here. Year-round retreat near ski, snowmobile, & hiking trails. Dogs ok!

Top guest favorite
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
4.92 out of 5 average rating, 158 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 favorite
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, 179 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!

Top guest favorite
The charming cottage exterior features wooden siding and a sloped roof with a dormer window. Flower baskets hang from the porch posts, adding color to the serene landscape. A gravel pathway leads to the entrance, framed by natural stone landscaping and lush greenery.
Cottage in Rice Lake
4.99 out of 5 average rating, 205 reviews

Stonehaven Cottages on Tuscobia Lake LLC.

The "Gatekeeper" cottage has a natural gas stone fireplace in the living room, Full size sofa sleeper, full kitchen, full bath on the main floor and a half bath in the sleeping loft. (Need to be able to climb ladder stairs to lofted bedroom). A spiral staircase leads you down to the lower level which has an additional bedroom, queen sofa sleeper in the extra living room space, and full bathroom. The lower level also has a walk out french door to the patio area.

Guest favorite
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, 412 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 favorite
A natural setting features a gathering area with four red Adirondack chairs arranged around a stone fire pit. A pathway of flat stones leads to a wooden deck with a green umbrella providing shade, surrounded by lush greenery typical of the Northwoods.
Cabin in Stone Lake
4.91 out of 5 average rating, 102 reviews

Slice of Paradise on Slim Lake

This cozy cabin in Stone Lake provides a true sense of the tranquil life in the Northwoods and is the perfect spot for your getaway! The cabin faces West on the charming and spring fed Slim Lake (great for swimming, recreation, and fishing). You can enjoy a morning coffee on either the deck or beautiful three season porch overlooking the water. It is a perfect spot for families and friends to make great memories at any time of the year!

Guest favorite
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
4.95 out of 5 average rating, 20 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.

Popular amenities for Hillsdale vacation rentals

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  4. Barron County
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