Holiday rentals in Osceola

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!

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!

Cabin On River’s Bend Campfire | Apple River

Perched high on the banks of the Apple River, the 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 3 private acres in Amery, WI you will be near rivers, lakes, hiking trails and all that Wisconsin Northwoods has to offer.

The Writers Cabin (Sauna/hot tub/river access)

Welcome to the writers cabin at wilder retreat on the saint Croix river. This place is for the dreamers, the star gazers, those craving the healing power of nature. The writers cabin is well appointed and designed for beauty and comfort. Enjoy access to the river as well as our wood fired sauna and wood fired hot tub. Equipped with a queen sized bed in the loft, cooktop, solar, and a pump sink. A gas fireplace keeps you warm in the winter. We invite you to come and rest, and leave restored.

Very private, country, wildlife, & comfort of home

Close to the St. Croix River and the Twin Cities. 2 State Parks within 10 minutes, and great dining in Hudson, River Falls, & Stillwater. Perfect for couples and family adventurers. 35 minutes from MSP and 1.5 miles off I-94. When things green up during spring and summer, it is a park like setting. Fall brings beautiful brilliant color. Winter brings cross county skiing, snowshoeing, tubing, and hiking. A treasure for nature enthusiasts. Natural setting with woods, deer, birds, turkeys.

Nostalgia Room - Downtown Loft w/ Views

Welcome to our modern 1-bedroom loft, centrally located in the heart of downtown North Branch. Housed in a beautifully restored 1920s building with modern decor, you can admire the Americana Coca Cola mural featured on the exterior of the building. The loft's central location means you're just a stone's throw away from essential amenities, including a quaint café, a health food store, and a women's clothing boutique conveniently located below. Everything you need is within arm's reach.

Riverside Retreat- A small cabin for big memories!

Renovated cabin nestled high in the pines overlooking the river. Kick back and relax in this calm, stylish space where the river views will take your breath away. We have a great selection of games, books and movies to snuggle up with in front of our warm fireplace. Bring your snowmobiles, ATVs and ice fishing gear as we are close to the Gandy Dancer Trails and our beautiful river flows to two lakes for great fishing - end at our bonfire pit to roast S'mores and swap stories!

Stay at this cute and cozy lakeside cabin

Come ski and stay, cabin located 1.5 miles from Trollhaugen Ski Resort. Just under 600 sq ft nestled in a wooded valley, on one acre with 200 feet of wild shoreline on nature-filled Lotus Lake. You'll love the peace and tranquility yet be amazed at how central the location is. The cabin is located next to the north entrance of the Stower 7-Lakes trail (walking, biking, horseback) and two miles from the beautiful Interstate Park and the amazing St. Croix River valley

Historic Home w Modern Updates Near Taylor's Falls

Cascade House has all the charm you could ask for in a historic house, and all the updates you need to stay cozy and comfortable. With a fireplace, office, and plenty of living space, you may never want to go out. But if you decide to venture out, Cascade House is just blocks from shops and restaurants in historic downtown Osceola, and minutes from hiking at national and state parks, kayaking, canoeing, skiing and ropes courses, and even ATV/Snowmobile trails.