Holiday rentals in Hillsdale

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Top-rated holiday rentals in Hillsdale

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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
4.95 out of 5 average rating, 195 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, 389 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
A cozy living area features a large blue sectional sofa and a comfortable brown armchair. A wooden coffee table is centered on a patterned area rug. Natural light enters through the window, adorned with white curtains, illuminating the space.
Home in Eau Claire
4.98 out of 5 average rating, 145 reviews

WanderInn Riverview

Nestled in a peaceful cul-de-sac, our cozy retreat offers the perfect getaway! Conveniently located near key thoroughfares, you're just minutes from public boat landings, beaches, parks, scenic bike trails, and downtown Eau Claire, making it easy to explore the area. Thoughtfully decorated with comfort in mind, our home provides a relaxing space to unwind. We take pride in using non-toxic cleaning products, ensuring a safe and eco-friendly stay. The ideal base for both relaxation and adventure!

Top guest favourite
Cabin in Comstock
4.97 out of 5 average rating, 229 reviews

Nordic Lake Cabin : Sauna/Hot Tub/Pontoon Rental

We finished building this modern Scandinavian cabin in spring 2020. It’s been featured in Vogue and on Magnolia Network. The cabin sits at the end of the road on a private lot with a perfect view of sunsets over the nature side of the lake. Drive past farm fields, into the woods, and onto our private gravel road, arriving at the driveway. Watch loons, tundra swans, eagles, beavers and deer while you relax by the lake. Pontoon boat rental is available as an add on! Pets welcome for a $90 fee!

Top guest favourite
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.
Flat in Elk Mound
4.94 out of 5 average rating, 476 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 favourite
A new house with a modern design is set among lush greenery, featuring a metal roof and large windows. The surrounding area includes neatly arranged evergreen trees and natural stone accents. A gravel driveway leads to the entrance, blending harmoniously with the outdoor landscape.
Tiny home in Grantsburg
4.97 out of 5 average rating, 640 reviews

Snowshoe Creek & Little Wood Lake Tiny House

New 520 sf 'not too tiny' house on 20 wilderness acres. Year 'round fun. Dog friendly. RV & EV plug. Firepit. Your Snowshoe Creek and Little Wood Lake trails. Free canoe, kayak, paddleboat. $40/day mini-pontoon boat. Fishing. Internet. WiFi. AC. Gas Fireplace. Sleep by Number. Lovely bathroom. New gas stove. Ice maker. 2 TVs. 3 towns + Burnett Dairy/Bistro, 4 golf courses, DQ to fine dining, mini-golf, antiquing, multi-theater, Siren beach & 'Music in Park'. Wildlife! You'll return.

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, 145 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, 166 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 favourite
Cabin in Saint Croix Falls
4.96 out of 5 average rating, 109 reviews

Cozy Lakeside Cabin + Woodstove by Interstate Park

Filled with the coziest vibes, vintage touches, and sun soaked windows, Alkov Cabin is your sweet little getaway about an hour from Minneapolis! Built in 2023 by the owners and filled with lots of old charm. Enjoy a fire overlooking the lake, a walk at a nearby nature preserve, a book on the sofa, all with a view of Bridget Lake in western WI. Minutes from charming downtown Balsam Lake, Interstate State Park, Trollhaugen Ski Area, and Balsam Lake Ski Trails. PCHD #77050

Top guest favourite
A welcoming interior features a large wooden archway that transitions between spaces. A cozy seating area is furnished with a comfortable sofa, with a soft throw draped across it. The room is illuminated by string lights, with a rustic stone fireplace adding charm.
Cottage in Rice Lake
4.98 out of 5 average rating, 129 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
An outdoor seating area is surrounded by trees, featuring a round metal table with chairs. The cabin, characterized by large windows and a welcoming entrance, is positioned nearby, with steps leading up to the porch. A fire pit area is also visible in the background.
Cabin in Cumberland
4.87 out of 5 average rating, 188 reviews

Cozy Cabin on Kirby Lake - Stuga Wald

Enjoy the peace and quiet of this quaint little cabin on Kirby Lake. If you are looking for rest and retreat, this place is for you! The cabin is open concept with the living space, dining, kitchen, and bathroom on the main level. The loft boasts two twin beds that each pull out into a king, as well as a pull-out couch downstairs. Enjoy the tranquility of a sunset paddle, evening campfire, the call of loons, and the simplicity Stuga Wald has to offer.

Popular amenities for Hillsdale holiday rentals

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