Holiday houses in Osceola

Tree House Luxury Stay

Perched high in the majestic arms of a 150 year old Burr White Oak tree. This cozy 1200 square foot, seven-room house not only has breathtaking views it also has enchanting and delightful surprises befitting of a fairytale. Climb 40 feet up onto the Observation Tower, where a telescope waits for you, ready to scan the night sky, and reveal the panorama of the heavens -- overlooking 500 acres of natural splendor right next door. Step into the hot, bubbling jets of the jacuzzi, or warm caress of the rain shower, and restore your spirits by soothing your muscles, melting away any residual tensions of the day. Get a restful sleep in one of our soft beds. In the morning, pad around on in-floor radiant heated floors (so cozy during winter-time.) Or enjoy your morning coffee on one of four outside decks. And don’t forget to solve the mystery of the Treehouse, that awaits your discovery within its wood beamed walls. This treehouse was custom designed by its architect with three dimensional chess in mind. Artisan architectural details are found throughout. Crystal chandeliers bedeck its high ceilings, and marble countertops grace the elegant, fully appointed kitchen. (A surround sound system helps set the mood for those special dinners in the dining nook.) One of two fireplaces adds luxurious touches to the primary bedroom with a queen bed, and hideaway bed in the secret room, along with a jacuzzi and rain shower in the primary bath, as well as a second bathroom in the secret room. Perfect for honeymooners, couples, business/corporate overnights, solo travelers and families with children over twelve years old. These are only a few of the many luxury details in this spectacular vacation spot must-see. Spend your days snuggled up beside the fireplace of your choice, while enjoying the panoramic views. You can stream your favorite movies and shows with Broadband Wi-Fi throughout the house. Come down for a leisurely walk around the grounds, and stop by to visit and feed the goats and chickens that call Hope Glen Farm their home in the corral of this historic farmstead. Bring your stress levels down and your heart rate up by walking over to Washington County Cottage Grove Park Reserve, just steps away, and answer its call to explore over 550 acres of fields and forests. Go hiking and biking down its trails, geocaching the hills and ravines for hidden treasures, or spend the afternoon fishing and kayaking in the lakes. And don’t let cooler temperatures keep you from discovering the pristine natural beauty of winter! Winter activities include cross country skiing and snowshoeing on the blankets of snow. Breathe deeply of the crisp Minnesota winter air -- truly one of life’s great pleasures. Plus, only a ten minute drive brings you to nearby Afton Alps in Afton State Park offering downhill skiing and snowboarding. For clarity, the Treehouse has 2 private bedrooms: Bedroom 1 is has a queen bed. Bedroom 2 has a bedroom with standard sofa bed with attached half bathroom, which is the secret room a must find. Give yourself the gift of this luxurious enchanting TreeHouse Suite in the treetops, for a enchanting vacation experience you'll never forget. Something to write home about!

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 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!

Dr Combacker’s Historic 1880s Home

Voted 2021 & 2023 Readers’ Choice Best Bed and Breakfast! Historic charm marries modern luxuries in this beautiful 1880s home. Built by the pioneering Dr. Henry Combacker, this one of a kind home boasts original woodwork and amazing craftsmanship. Families and groups alike will enjoy the fully stocked kitchen, outdoor living spaces, entertainment for all ages, attention to detail, and close to downtown location. Dr. Combacker’s has all you need for a calm, relaxing stay in and out and about.

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.

The Writers Cabin-Sauna/hot tub/river access

Welcome to the Writer’s Cabin at Wilder Retreat on the Saint Croix. A place to unplug and unwind. Designed to slow you down and reconnect you with nature. This thoughtfully designed tiny cabin blends beauty and comfort, with access to the saint croix river and use of wood-fired sauna and wood-fired hot tub and outdoor shower. The cabin features a queen bed in the loft, cooktop, solar power, and a pump sink. A gas fireplace keeps things cozy in the winter months. Come to rest. Leave restored.

Hiker's Hideaway: 4BR+Porch+Updated 1872 Home

Fall in love with Taylors Falls! This 1872 built 4-bedroom charmer in historic Taylors Falls sleeps 8 comfortably with 2 full baths (1 shower) - perfect for families or groups seeking a relaxing escape. Unwind in the clawfoot tub after exploring cascading waterfalls and scenic trails. Savor evenings on the porch, embraced by the surrounding nature. Just minutes away, discover charming shops, art galleries, and cafes. Angel Hill awaits - your haven for a memorable Taylors Falls adventure!

The Cellar @ Porter's Corner

Escape to The Cellar. This historic suite is built as an 1800s saloon, where timeless charm meets modern indulgence. Relax in the king bed, unwind in the deep soaking tub, or refresh under the rain fall shower. Located steps from downtown Taylors Falls, you’ll be perfectly positioned to explore scenic hiking trails, local restaurants, and the natural beauty of the St. Croix River Valley. Whether you’re here for adventure or relaxation, The Cellar offers a cozy, unforgettable getaway!

Scandinavian Retreat

A perfect getaway! The fully updated home features Scandinavian design and a one-of-a-kind spiral staircase! A truly cozy space - dim the lights & enjoy the ambiance. The sunroom is a perfect place to relax w/ a cup of coffee surrounded by plants & greenery. Taylors Falls offers great outdoor adventures like hiking in Interstate State Park, activities on the St. Croix River, and exploring the Franconia Sculpture Park, with the added bonus of good restaurants and beautiful landscapes!

Stylle Hytte ///\ Northern Cabin Retreat

Our Nordic inspired A-Frame is known as the Stylle Hytte which is Norwegian for ‘Quiet Cabin’. Here you can take in 5 secluded acres of woods with trails winding down to the private riverfront. Only an hour north of the Twin Cities, enjoy modern conveniences like WIFI (60mbps), smart TV, complete kitchen, full bathroom, a bedroom and loft both with queen beds, a cozy living room with a real wood fireplace and an outdoor electric barrel sauna. Calendars are open 9 months in advance.

Cambrian& Co Chic Downtown Falls Overlook Loft

Discover your luxurious getaway at this chic, stylish, downtown loft—steps from Interstate State Park and scenic trails. In winter, ski Trollhaugen or Wild Mountain; in summer, enjoy water parks, go-karts, and mini golf. Paddle the St. Croix River, stroll charming shops, and end with wine at a vineyard or craft brews at a local brewery. Elegant décor, plush comforts, and a prime downtown location make this a refined retreat for every season—where adventure meets indulgence.

Lakefront Home with 6-person Hot Tub

Welcome to Pleasant Lake. Pleasant Lake 4 bed, 4.5 bath 3200 SF home with a hot tub that sits on 2.5 acres with panoramic views from the house and deck overlooking our semi-private 40 acre lake. Pleasant Lake has been adored by guests as a Bed & Breakfast since 1989 on property owned by the Berg family since 1896. After a full renovation completed in the summer of 2024, our lake home is now ready for a new chapter of making family & friend memories and enjoying lake life!