Holiday rentals in Hillsdale

Cozy Mother-In-Law Apartment—No Cleaning Fee!

Voted 2021 and 2023 Readers’ Choice Best Bed & Breakfast! Steal your getaway at one of Osceola’s most historic estates. Wonderfully nestled in the St. Croix Valley, this apartment’s location will not disappoint. You’ll be a brief walk from beautiful downtown Osceola, close enough to explore the great outdoors, and a short distance from all that the Twin Cities has to offer. You’ll get a cozy and comfortable layout, thoughtful amenities, attached heated garage, and assistance just a message away!

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!

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.

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!

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.

Cozy 3Bd2Bth Cabin at the Lake: Pines That Whisper

Escape to the country! Discover "Pines" that Whisper located in rural Balsam Lake WI. Our cozy cottage is only a stones throw away from beautiful Half Moon Lake with public access to a boat launch, fishing pier and swimming beach. Enjoy fishing, kayaking, biking and leisurely walks on country roads. Connect with nature and wide open spaces. We are nestled in a private setting surrounded by farm fields. Envision wildlife passing by, loons calling in the distance, & breathtaking sunsets!

Water's Edge House on Tainter Lake

Gorgeous little house with cap cod feel, right on the water. We call this baby "Water's Edge on Tainter Lake". Perfect way for a quick escape from the Twin cities, only 50 minutes away. Fish off the permanent dock on the water. Beautiful views and sunsets on a fun, active recreational lake. Short boat ride to Jake's super club. Some guests say its a "private location", but we are on a very active lake with houses close by. Please read our "other details to note" for more info.

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.

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.

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!

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"!

Cabin 2 - Northwoods themed 1 BR, lakefront cabin.

Relax in this cozy, newly remodeled, 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.