Holiday rentals in Osseo

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Location · Value · Heating

Little House in the Valley

Little House in the Valley is a must-see property, carefully restored to maintain it's original farmhouse charm while adding the modern touches needed to unwind & recharge. It is situated at the end of a private road, surrounded by 120 acres of fields & rolling hills- a nature lover's dream. Located just minutes from town, golf courses, local wedding venues, snowmobile trails, wineries & so much more. Relax & allow yourself to be embraced by the calming, natural charm of this home.

Family · Location · Check-in

A Suite Getaway

You'll love this place because of the spectacular views, horses, wildlife, fishing, hiking and hot tub for relaxing, a romantic getaway or simply just girl time. This spot is perfect for couples or solo adventurers! A unique suite is attached to an elegant vintage peg barn. Space for bringing horses, snowmobiles or ATV's since we have trails. A mile away from snowmobile trails and 25 mins from a State Park. Also, perfect for snowshoeing and cross country skiing. Fire pit available.

Family · Value · River

Country Retreat. Beautiful sunsets and sunrises.

Fresh country air. Beautiful view. Cable TV. Wi-Fi. Hot Tub (chemical free). Spacious furnished kitchen. Sectional sofa with recliners. Recliner. Electric fireplace. Outdoor firepit (bring your own wood). Washer and dryer. 12 inch step into tub/shower. This beautiful getaway is attached to the family business shop. We do load trailers occasionally and will be working in shop at times. Minimal noise. 30 Minutes from Eau Claire. We are only 25 minutes from two lakes with beaches.

Family · Location · Wifi

The Lily Pad: Retro 4BR w/ Hot Tub on Lake Wissota

This unique lake house has a style all its own. Our pad has a vintage vibe and stunning lake views. You're only 10 steps to Lake Wissota from the back door. Across the road you'll find 24 acres of conservancy land with hiking trails. This home makes the perfect getaway for any time of year. Our 4 bedroom, 2 bath lake house comes with a full kitchen, a private dock, 2 queen beds, 1 full bed, 1 twin bed and a futon. Explore nearby Lake Wissota or tour the Leinie Lodge.

Location · Family · Long stay

The Old Mill

The Old Mill is a beautiful, fully-furnished vacation rental nestled on the banks of Lake Henry and the Trempealeau River in Blair, WI. The Old Mill is perfect for anyone looking to curl up with a good book and enjoy the serenity of a peaceful atmosphere, or for the outdoors enthusiast looking to spend the weekend outdoors doing what they love. Whether you are interested in hunting, fishing, or enjoying local wineries, you'll find the perfect accommodations nearby.

Family · Value · Sleep quality

Barstow Cottage

This 19th century cottage is renovated with architectural elements to bring back its history. Backyard is meant for inviting family and friends. Stroll 3 blocks behind cottage & walk along river to see Eau Claire's oldest lumber mansions. At south end of downtown, you're close to everything - shops, food, nightlife! Note: If you're visiting Mayo for MEDICAL staying 7 days, we discount $125 off total. (need proof of clinic visit, Thank you)

Value · Location · Quiet

The RidgeHaus: 40-Acre Farm Stay, Fire Pit & Views

Escape to The RidgeHaus, a horse-friendly retreat on 40 acres in Hixton’s rolling hills. Home to our grazing cattle, part of the land is reserved for the herd, but guests enjoy private yard space, fire pit, and trailer/ATV parking. Stroll quiet country roads, explore antique shops, orchards, and trails, or hunt nearby public lands. Inside, enjoy a full kitchen, high-speed WiFi, and cozy spaces to relax under Wisconsin’s starry skies.

Family · Location · Decor

The Keep at Pleasant Valley | Country Retreat

Rest easy in our handcrafted country retreat just 15 minutes from Eau Claire and 35 minutes from Cadott. Sip your coffee by the fire in the morning and listen to the crickets sing as you watch the stars come awake in the evening. The Keep features a full kitchen with custom hickory and cedar cabinetry, in floor heat for chilly nights, and a large private patio—perfect for grilling out or roasting s’mores. See you soon at the Keep!

Location · Family · Amenities

The Granary Guesthouse @ Harvest Home Farm

Harvest Home Farm is located at the end of a dead end road nestled in a valley, just 4 miles northeast of Whitehall, Wisconsin, in beautiful Trempealeau County. The 160 acre farm has a long term focus on raising grass fed sheep and poultry. We also have a produce garden, a berry patch, and an apple orchard. The farm has 80 acres of mixed hardwoods and softwoods and an abundance of wildlife as well as a network of walking trails.

Location · Family · Hospitality

The Fox Den Guesthouse

Located just 3 miles from I94/State Hwy 121/Northfield, The Fox Den Guesthouse is a perfect option to spend some time enjoying the Wisconsin countryside. Situated on the UTV route with easy access to numerous trails and ample truck and trailer parking! Also near many options for public hunting and fishing! The home is ADA compliant, no steps! Sit on the front porch and enjoy watching the cattle graze.

Location · Family · Amenities

Secluded Modern Farmhouse

Escape the busy day to day hustle and come relax at this secluded stylish farmhouse located on peaceful private road and 30 acres. Spend time hiking, snowshoeing, or relaxing by the fire pit. Bring the snowmobiles, or UTV'S / ATV'S and jump on the trails. Home offers 3 bedrooms, 2 bathrooms, laundry, custom kitchen, and a 2 car attached garage. We are pet friendly and offer high speed internet.

Family · Location · Hiking