Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Guest favorite

A living room features a stone fireplace and a large window allowing natural light. A leather couch faces a wooden coffee table, with built-in bookshelves nearby. Soft drapes frame the window, enhancing the serene view of the garden outside.

Cottage in Taylors Falls

4.91 out of 5 average rating, 103 reviews

Grove Cottage walkable retreat in St. Croix Valley

Nestled in the St. Croix Valley, this historic cottage is within walking distance of downtown Taylors Falls and Interstate Park. Centrally located between two ski hills, this is a great location for year-round enjoyment. Within minutes of ATV/snowmobile and bike trails, canoeing, kayaking, and gorgeous fall color displays. Within easy distance of Osceola and Stillwater. The charming home includes all the modern comforts with a spacious yard and garden to relax and unwind, including a fire pit

Top guest favorite

A light-filled living space features a comfortable leather sofa, a wooden coffee table, and a flat-screen TV mounted on a wooden cabinet. A round dining table with two chairs is positioned near the window. Decorative horse-themed accents are visible on some furnishings.

Guest suite in Osceola

4.96 out of 5 average rating, 252 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

A rustic cabin exterior features wooden siding and a sloping roof. Two rocking chairs are placed on the front porch, framed by large windows adorned with lace curtains. Surrounding trees display vibrant autumn foliage, enhancing the natural setting.

Place to stay in Saint Croix Falls

4.94 out of 5 average rating, 340 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 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

4.91 out of 5 average rating, 212 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

The cozy timber-framed cabin is surrounded by lush greenery and colorful fall foliage. A vibrant orange tree contrasts with the cabin's exterior, while flowering plants and shrubs create a natural border, enhancing the cabin's secluded atmosphere amidst the serene wooded landscape.

Cabin in Amery

5 out of 5 average rating, 154 reviews

Timber-framed Cabin On River’s Bend | 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.

Top guest favorite

A warmly illuminated bedroom features a carved wooden bed frame with tall posts, draped in soft linens. Architectural accents include arched doorways and decorative windows, contributing to the room's unique character. A cozy textured blanket is placed atop the bed, enhancing the inviting space.

Loft in Saint Croix Falls

4.98 out of 5 average rating, 176 reviews

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

Top guest favorite

The modern retreat features an expansive outdoor patio with comfortable seating arrangements. Large windows accentuate the two-story structure, revealing a seamless blend of indoor and outdoor living areas. Surrounding tall trees provide a sense of isolation and tranquility.

Home in Somerset

4.98 out of 5 average rating, 123 reviews

Lake House Retreat: Modern, Stylish, Arty, Fun

Secluded modern design, fun, stylish, lakefront retreat carefully nestled in mature pines on 2.5 acres with 120 feet of easily accessible shoreline and large spa for year-round activities. A new build for families, groups, and pets on a countryside neighborhood. The indoors and outdoors are connected through careful positioning of many large windows, sliding doors, courtyard-like patio and rooftop deck. Cleaned by professional American House Cleaning Association certified COVID-19 cleaners.

Top guest favorite

A tranquil cabin is nestled among tall trees, with soft lighting emanating from its windows. A wooden walkway leads to the entrance, inviting guests into a harmonious natural setting. The roof features a classic red color, complementing the surrounding greenery.

Cabin in Grantsburg

4.95 out of 5 average rating, 701 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.

Guest favorite

A small black wooden cabin is surrounded by greenery, featuring exterior string lights that add a gentle glow. An outdoor seating area with an Adirondack chair sits nearby, alongside a fire pit. The rustic cabin design harmonizes with the natural landscape.

Tiny home in Shafer

4.86 out of 5 average rating, 153 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

The exterior of a rustic barn-style building is shown, featuring a large window and a bright red door. Solar panels are mounted on the front, with greenery and vibrant foliage in the foreground, enhancing the natural setting. A clear blue sky complements the serene environment.

Barn in Saint Croix Falls

4.97 out of 5 average rating, 105 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

The exterior of the home features a covered entrance with wooden beams and a welcoming sign. Snow falls gently, creating a serene atmosphere. Large double doors with glass panels are flanked by multiple windows, while a porch area contains seating and a clear view of the snowy surroundings.

Home in Osceola

4.97 out of 5 average rating, 32 reviews

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!

Guest favorite

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, 178 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.