Vacation 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!

Wolf Creek Luxury Eco-Tiny Home on the Ridge

Experience our newly-built eco-friendly tiny home perched right on the edge of the ridge above the majestic St Croix River Valley. Enjoy expansive views from the deck, the loft or the many windows looking out over the valley. Enjoy our private electric barrel-sauna, fire-pit, gas grill, pond with canoes and kayak, Wolf Creek with 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!

Luxury Barn Cottage and Villa at Hope Glen Farm

The Corn Crib Cottage Barn or Villa is a luxurious and rustic 1100 square foot space. The Corn Crib originally used to dry corn and animal housing. This is a very rare historical building built in the 1920's The villa has a 2 person whirlpool jacuzzi , rain shower, beautiful full kitchen, fireplace and next to the 550 acre Washington County Cottage Grove Ravine regional park reserve. The Cottage is near the famous lofty lodge treehouse in the area. Treehouse on airbnb listing number 14059804

The Artists Loft - walk to Interstate park

Welcome to the Artist’s Loft — a private, 1 bedroom apartment. This bright, spacious loft comfortably sleeps up to 4 adults with a queen bed, a deep, cozy couch, and a twin daybed in the living area. You'll enjoy a fully equipped kitchen, high-speed Wi-Fi, and plenty of natural light. Located just minutes from Interstate Park, downtown shops, art galleries, and river trails, the Artist’s Loft is your cozy home base for hiking, paddling, exploring — or just relaxing. Insta @123swashington

The Writers Cabin-Sauna/hot tub/river access

Welcome to the writers cabin at wilder retreat on the saint croix. A place to unplug and unwind to connect more, and experience the healing power of nature. The cabin/tiny house 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 power, and a pump sink. A gas fireplace keeps you warm in the winter. We invite you to come and rest, and leave restored.

Quiet Seclusion at Trade River Retreat Cabin

Remote, tranquil, quiet and exceedingly private getaway right on the banks of a protected river, only 1.5 hours from the Twin Cities! Even the beautiful drive there is relaxing. Enter a world of peace and calm deep in the woods. Make delicious meals in a well-stocked modern high-end kitchen, play in the river, relax in the sauna or enjoy a bonfire. This is not your typical cabin but a spiritual eco-oasis with a unique eclectic blend of modern, rustic, Native American and Japanese aesthetic.

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.

PoCo Cabin

Relax with the whole family at this lakefront cabin. Sit on the deck to hear the loons and enjoy the "best view on the lake" according to the neighbors. All new furniture and appliances are sure to have you comfortable as can be. Turn on the gas fireplace if you need to take the chill off, or just for some ambiance as you nestle into the couch for a movie. The two bedrooms are appointed with new beds and linens. The couch opens to a comfortable bed for more personal space if needed.

Romantic Lakeside Loft.

A wonderful lakeside getaway, with beautiful lake views from your suite and deck. Guest suite includes full kitchen, living room with fireplace, bedroom with attached full bath. Private entrance on side of home with your own private deck for lounging. dining and grilling. Large yard for playing games, fire pit and outdoor tiki bar. Plenty of dock space for boats. Direct access to lake for floating ,paddling, swimming, fishing and relaxing. Paddleboard and kayak available for your use.

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.

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