Vacation rentals in Osceola

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!

Value · Location · Solo travel

River Haus Where Good Times&Great Memories Happen!

The River Haus is located on 59 wooded acres with 1200 ft. of riverfront. The home is tucked back in the woods with a 3/4 mile long private drive, offering complete privacy. There are beautiful views of the St. Croix River from the deck, access to the river, dock, and amazing walking trails. The home is a log- sided cabin from the 1930s maintaining its original charm with vaulted ceilings, wood beams, and wood floors. Near downhill & cross-country skiing at Wild Mt. & William O'Brian State Park

Location · Family · Decor

Lakefront Cabin | Amazing Views | Kayaks Wildlife

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

Value · Family · Condition

The Greenhouse. Lakefront cabin

This 3 bed 1 bath newly custom built cabin sits perched above Middle Pine Lake, nestled into a quiet hillside forest. Filled with natural light, it’s a perfect retreat into nature and a great base for exploring NW Wisconsin. Features a dock and floating dock to enjoy the lake outside and a wood-burning stove for cozy nights inside. Designed for beauty and comfort, this well-appointed, efficient cabin is the perfect place to spend a peaceful lakeside cabin getaway or a fun-filled family vacation!

Family · Location · View

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.

Value · Family · Checkout

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!

Location · Family · TV

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!

Value · Family · Quiet

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!

Location · Family · Grill

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.

Location · Family · Condition

Lakefront-Firepit-snowmobile trails-ice fishing

Welcome to your very own private retreat on North Center Lake! A short drive from the twin cities brings you to the wonderful city of Lindstrom. This home is situated on over an acre on North Center Lake with beautiful trees surrounding the property to allow for plenty of privacy. This home can sleep up to 8 people. It provides 2 queen beds, 1 full bed and 2 twin beds. North Center Lake is one of the chain of lakes is Chisago County and is known for great bass fishing.

Value · Family · Skiing

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

Location · Value · Indoor spaces

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.

Value · Location · Wifi