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 · Grill

Bellevue bnb

This newly remodeled, conveniently located house is so comfortable that you won't want to go home. Memory foam beds in every room provide restful sleep and the 65 inch TV is perfect for watching your favorite shows or games. Enjoy the spacious front and back porch with friends and family. Off street parking, fully equipped kitchen, comfy patio furniture, coffee bar, spotless rooms, washer and dryer and unique artwork are just a few of the things that will make your stay relaxing and memorable.

Location · Value · Kitchen

Spacious House on Lake Altoona — incredible views

Welcome to our midcentury home perched high on the hill, overlooking sparkling Lake Altoona. Nestled among the pines, it feels like a private escape—yet you’re just steps from River Prairie Park and only minutes from town. With sweeping views, glowing sunsets, and thoughtful touches throughout, this space is designed for connection. Bring the whole family. The kids will love the movie theater downstairs. *Event friendly to 15+ (book club, meditation, baby showers, etc) **Eco-friendly home*

Family · Location · View

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.

Location · Value · Amenities

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.

Value · Family · Indoor spaces

Elk Creek Vista: Quaint 3br Home

Our home is a great space for people who want to experience nature, while also being a short drive from city comforts. Centrally located between Eau Claire, Lacrosse, and the Mississippi River, you are right near many outdoor activities throughout the year. At the house, you also have a screened in porch off the back which is a great place to enjoy your coffee in the morning or a book in the evening. Our water is the best as we have a reverse osmosis system.

Location · Family · Quiet

Living Waters Cabin Getaway

Stunning 92 acre property. Fishing, swimming, hiking, biking, birding, campfires all in an atmosphere of the great outdoors. Spacious bedroom overlooks acres of wooded scenery and landscapes of the rolling hills of Western Wisconsin. Owners home is located approx. 200 ft from cabin. A 2.5 car garage separates buildings. Second Airbnb is located approximately 200 feet from Cabin however no shared areas and completely private and separate from each other.

Location · Value · Pets

Med Park House

Bring the whole family to this great place with lots of room for fun. 4 bedroom 2 full bath house, comes with TV and wifi, pots and pans for cooking, plates, cutlery etc. Pond in the backyard for swimming and fishing, Zipline , private overhang for family get togethers, We also have campers so you may have occasional neighbors! This is country living, nothing fancy but homey and comfy!! As of Oct 2025, we have added a shower house by the pond!

Location · Family · Grill

Sonney Lodge

Perched on a hilltop in scenic Newcomb Valley, Sonney Lodge provides a quiet, country setting while still only a 10 minute drive to downtown Arcadia. Located on a dead end with a private drive and no through traffic, the lodge features 3 bedrooms, 2 bathrooms, a full kitchen, dining room and lower level entertainment room. A covered deck wraps around 2 sides of the home offering spectacular views of the surrounding hills and countryside.

Value · Location · Parking

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.

Location · Family · Hiking

Stunning Lakefront Home-Private Beach & Much More!

This beautiful log home is just steps away from the lake and has 100 feet of private beach and a large dock to relax on! Whether you are looking for a retreat in winter, spring, summer or fall - - this unique treasure has it ALL! Use of a kayak, canoe and stand-up paddleboard included in summer. Use of ice skates included in winter. This gem of a property is also dog friendly! Perfect place for a business team getaway as well.

Value · Location · TV

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!

Family · Location · Cleanliness