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

4.92 out of 5 average rating, 106 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, 255 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, 357 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 favorite

An aerial view showcases a rural property featuring multiple buildings, including a large red barn, a farmhouse, and a smaller structure. Lush greenery surrounds the area, with trees and an open field visible. Pathways connect the buildings, creating an inviting outdoor space.

Farm stay in Cottage Grove

4.96 out of 5 average rating, 542 reviews

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

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, 157 reviews

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.

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, 709 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.

Top guest favorite

An outdoor seating area features two red cushioned chairs and a small glass table, positioned around a circular fire pit. Soft light illuminates the space from a nearby lamp, with greenery and flowers visible in the background, creating a serene atmosphere.

Farm stay in Roberts

4.87 out of 5 average rating, 332 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 comfortable outdoor seating area is shown, featuring a cushioned sectional arranged around a wooden deck. An umbrella provides shade, while a serene view of the lake and boats is visible in the background. Colorful flowers are positioned along the railing.

Guest suite in Forest Lake

4.9 out of 5 average rating, 206 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.

Top 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, 106 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.

Guest favorite

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

4.96 out of 5 average rating, 76 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 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, 182 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 favorite

A cozy seating area is situated under the shade of trees, featuring two adirondack chairs positioned for relaxation. In the background, a yurt-style tent is visible, surrounded by lush greenery. A picnic table can be seen nearby, enhancing the camping experience.

Campsite in Shafer

4.93 out of 5 average rating, 107 reviews

Yurt-Style Tent at Stone Creek Farm

1 of 4 campsites on the farm, this yurt-style tent has all you need to enjoy camping without the work! The campsite includes a picnic table, BBQ grill and fire pit. There is a self composting toilet on site. Camp carts available to bring gear out. Drinking water is available from the hose out by the high tunnel. It is about a quarter mile walk to the site. If this site is booked when you want to stay, check out our new sites Peachy Keen and Plum Perfect!