Places to stay in Osceola

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Top-rated places to stay in Osceola

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

Two red Adirondack chairs sit on a dock overlooking a misty lake at twilight. The surface of the water reflects the blue sky, with a full moon visible. Surrounding trees create a serene backdrop, adding to the tranquil atmosphere of the bay.

Cabin in Amery

5 out of 5 average rating, 113 reviews

Vintage Modern Lake Cabin | Unique Design w/Kayaks

Welcome to The Backwater, a newly built architect designed year-round getaway on Pike Lake in Amery, WI. Nestled in the back of a quiet, lilypad-filled bay teeming with wildlife, our cabin is the perfect destination for guests who appreciate original design and crave a unique experience. Our amenities are luxurious, but our attitude is chill inside our comfy, creative digs full of nostalgic, vintage vibes. Come stay and play on the bay while enjoying Polk Co.! Follow along @thebackwater_wi on IG

Top guest favorite

An antique lantern hangs from the ceiling, casting a warm glow. A wooden shelf displays a collection of vintage bottles and an assortment of rustic decor items. Neutral-colored walls complement the charming, nostalgic ambiance of the space.

Guest suite in Osceola

4.96 out of 5 average rating, 240 reviews

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!

Top guest favorite

An old wooden trestle stands tall amidst autumn foliage, supported by robust wooden beams and crisscrossed bracing. The structural details of weathered wood are prominent, contrasting with the surrounding greenery and fallen leaves on the forest floor.

Place to stay in Saint Croix Falls

4.94 out of 5 average rating, 319 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!

Guest favorite

A newly-built tiny home with a rustic exterior is positioned on the ridge, overlooking a valley at sunset. The deck features seating, while the surrounding landscape includes patches of snow and tall grasses, creating a serene environment.

Tiny home in Saint Croix Falls

4.92 out of 5 average rating, 204 reviews

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!

Top guest favorite

Cabin in Grantsburg

4.95 out of 5 average rating, 689 reviews

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.

Superhost

A wood-fired sauna is depicted, featuring a glowing fire within a small stove. Smooth stones are arranged around the stove, and a bucket with a ladle rests nearby. The wooden walls and benches create a warm, inviting environment.

Tiny home in Shafer

4.86 out of 5 average rating, 147 reviews

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.

Guest favorite

A winding pathway, composed of gray stones and bordered by red mulch, leads through a wooded area. The path is lined with soft-glowing lights that provide a gentle illumination. Lush greenery surrounds the pathway, creating a serene outdoor environment.

Farm stay in Roberts

4.87 out of 5 average rating, 317 reviews

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.

Superhost

A street view of downtown North Branch is captured at night, showcasing illuminated storefronts and the Americana Coca Cola mural on a nearby building. Streetlights provide warm lighting, while light trails from passing vehicles add a dynamic element to the scene.

Loft in North Branch

4.81 out of 5 average rating, 219 reviews

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.

Superhost

A wooden sign is displayed, featuring the text 'Lakeside Loft Parking' in large, bold letters. The sign is framed in a rustic wood border and includes decorative elements such as crossed oars. A small American flag is positioned nearby, and a well-maintained lawn is visible in the background.

Guest suite in Forest Lake

4.91 out of 5 average rating, 192 reviews

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.

Guest favorite

Barn in Saint Croix Falls

4.97 out of 5 average rating, 103 reviews

Simple and Serene

The Stable is one of several live/work studios on a property that hosts artists in retreat and those seeking time for spiritual sustenance and personal reflection. We also enjoy hosting tourists who align with our mission. This 20x25 studio has an electric stove, fridge, container water, and a piano! It's served by a privy just a few steps from the door. Our community thrives on healthy wholistic living. Residents and guests agree to remain alcohol and drug free during their stay.

Top guest favorite

Large windows frame serene views of the river and surrounding pine trees, inviting natural light into the space. A cozy area rug lies on the floor, complementing the wood flooring and adjacent to a small kitchenette featuring simple cabinetry.

Cabin in Webster

4.97 out of 5 average rating, 156 reviews

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!

Guest favorite

A scenic view overlooking a river valley is framed by bare trees and a wooden fence. A bench is positioned on a paved area, inviting guests to relax and take in the natural beauty of the surroundings.

Home in Osceola

4.93 out of 5 average rating, 173 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.