Holiday houses in Osceola

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Top-rated holiday rentals in Osceola

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Top Guest favourite
A cozy tiny home is illuminated at night, revealing warm light from its windows. A stone pathway leads to an inviting front deck surrounded by greenery. Nearby, a decorative lantern can be seen in the foreground, enhancing the serene ambiance.
Tiny home in Saint Croix Falls
4.92 out of 5 average rating, 275 reviews

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!

Top Guest favourite
Place to stay in Saint Croix Falls
4.95 out of 5 average rating, 432 reviews

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!

Top Guest favourite
Loft in Saint Croix Falls
4.98 out of 5 average rating, 207 reviews

Romantic, Walk to Park, Located on Main Street

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

Top Guest favourite
A charming two-story home with a yellow exterior is presented, showcasing a welcoming front porch adorned with hanging planters. The roof features gables and multiple windows, contributing to its classic design. A spacious lawn leads to a paved walkway, offering easy access to the entrance.
Townhouse in Osceola
4.98 out of 5 average rating, 200 reviews

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.

Guest favourite
Tiny home in Shafer
4.87 out of 5 average rating, 175 reviews

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.

Top Guest favourite
Home in Taylors Falls
4.96 out of 5 average rating, 76 reviews

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!

Superhost
The A-frame cabin showcases a wooden exterior with large glass doors, allowing a glimpse into the inviting interior. Surrounded by lush trees, a spacious front deck is visible, featuring outdoor seating and a propane grill, perfect for outdoor gatherings.
Cabin in Brook Park
4.89 out of 5 average rating, 295 reviews

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.

Guest favourite
A cozy seating area is presented with a blue sofa and two brown accent chairs. A geometric coffee table rests on a light area rug. The walls feature a floral design, and a large ornate mirror adds depth to the space. Warm lighting enhances the atmosphere.
Apartment in Taylors Falls
4.93 out of 5 average rating, 29 reviews

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.

Top Guest favourite
A charming cabin is set amidst lush greenery, featuring a dark exterior with wooden accents. The entrance is framed with a star design, and a small porch area provides an outdoor sitting space. A grassy yard extends in front, ideal for relaxation.
Cabin in Osceola
4.97 out of 5 average rating, 94 reviews

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

Guest favourite
A welcoming living area features a patterned area rug centered on a warm hardwood floor. Two armchairs and a small table complement a cozy seating arrangement, while a decorative fireplace adds charm. A workspace with a chair and desk is visible in the background.
Home in Osceola
4.93 out of 5 average rating, 202 reviews

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.

Guest favourite
A glass house reflects natural surroundings, enclosed by trees and sunlight. The interior features a spacious bed draped in white linens, with cozy seating visible nearby. A wooden deck extends outwards, complemented by outdoor furniture and decorative lanterns.
Dome in Afton
4.87 out of 5 average rating, 412 reviews

Star Gazing Glass House 4 Season with Hot Tub

This glass house has a mini split offering both heat and air conditioning. There is something truly magical about being submersed in nature. Watching beautiful snowflakes cascade around its walls, snuggled under heated blankets while star gazing. Rainstorms have a new meaning, sunsets and sunrises become a life-changing experience. This is a photographer's dream, a romantic getaway, or the perfect place to reconnect with yourself. Private hot tub and fire pit.

Top Guest favourite
A rustic cottage is seen among a natural setting, featuring a red roof and colorful door. White clapboard walls contrast with the vibrant red window frames. Surrounding foliage exhibit autumn hues, and grassy areas are visible in the foreground, adding to the serene landscape.
Cottage in Saint Croix Falls
4.97 out of 5 average rating, 103 reviews

Creativity and Contemplation

Our forty-acre immigrant farmstead hosts retreat guests committed to creativity, spirituality, and learning. We're near several rivers and the city of trails. We have five kilometers of trails on the property with woods, prairie, and ponds for walking, birding, cross-country skiing, and delight. We prize healthy holistic living. Guests and residents choose to remain free of alcohol and drugs. Please tell us a little about the reason for your stay.

Popular amenities for Osceola holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Polk County
  5. Osceola