Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Guest favorite

Home in Cottage Grove

4.98 out of 5 average rating, 648 reviews

Tree House Luxury Stay

Perched high in the majestic arms of a 150 year old Burr White Oak tree. This cozy 1200 square foot, seven-room house not only has breathtaking views it also has enchanting and delightful surprises befitting of a fairytale. Climb 40 feet up onto the Observation Tower, where a telescope waits for you, ready to scan the night sky, and reveal the panorama of the heavens -- overlooking 500 acres of natural splendor right next door. Step into the hot, bubbling jets of the jacuzzi, or warm caress of the rain shower, and restore your spirits by soothing your muscles, melting away any residual tensions of the day. Get a restful sleep in one of our soft beds. In the morning, pad around on in-floor radiant heated floors (so cozy during winter-time.) Or enjoy your morning coffee on one of four outside decks. And don’t forget to solve the mystery of the Treehouse, that awaits your discovery within its wood beamed walls. This treehouse was custom designed by its architect with three dimensional chess in mind. Artisan architectural details are found throughout. Crystal chandeliers bedeck its high ceilings, and marble countertops grace the elegant, fully appointed kitchen. (A surround sound system helps set the mood for those special dinners in the dining nook.) One of two fireplaces adds luxurious touches to the primary bedroom with a queen bed, and hideaway bed in the secret room, along with a jacuzzi and rain shower in the primary bath, as well as a second bathroom in the secret room. Perfect for honeymooners, couples, business/corporate overnights, solo travelers and families with children over twelve years old. These are only a few of the many luxury details in this spectacular vacation spot must-see. Spend your days snuggled up beside the fireplace of your choice, while enjoying the panoramic views. You can stream your favorite movies and shows with Broadband Wi-Fi throughout the house. Come down for a leisurely walk around the grounds, and stop by to visit and feed the goats and chickens that call Hope Glen Farm their home in the corral of this historic farmstead. Bring your stress levels down and your heart rate up by walking over to Washington County Cottage Grove Park Reserve, just steps away, and answer its call to explore over 550 acres of fields and forests. Go hiking and biking down its trails, geocaching the hills and ravines for hidden treasures, or spend the afternoon fishing and kayaking in the lakes. And don’t let cooler temperatures keep you from discovering the pristine natural beauty of winter! Winter activities include cross country skiing and snowshoeing on the blankets of snow. Breathe deeply of the crisp Minnesota winter air -- truly one of life’s great pleasures. Plus, only a ten minute drive brings you to nearby Afton Alps in Afton State Park offering downhill skiing and snowboarding. For clarity, the Treehouse has 2 private bedrooms: Bedroom 1 is has a queen bed. Bedroom 2 has a bedroom with standard sofa bed with attached half bathroom, which is the secret room a must find. Give yourself the gift of this luxurious enchanting TreeHouse Suite in the treetops, for a enchanting vacation experience you'll never forget. Something to write home about!

Guest favorite

Guest suite in Osceola

4.96 out of 5 average rating, 230 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!

Guest favorite

Place to stay in Saint Croix Falls

4.94 out of 5 average rating, 250 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

Cabin in Grantsburg

4.95 out of 5 average rating, 642 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

Cabin in Amery

5 out of 5 average rating, 133 reviews

On River’s Bend cabin stunning view of Apple River

Perched high on the banks of the Apple River, this timber-framed cabin offers spectacular views of the river and wildlife. We’ve seen bald eagles, deer, ducks, geese, great blue heron, golden eagle, fox, beaver, bear and wild turkey from the comfort of the cabin. Just one hour from the twin cities, it’s the perfect cabin getaway for couples or families. Located on a private 3-acre lot <10 miles from Amery, WI you’ll be near hiking and biking trails and all that Northwest WI has to offer.

Guest favorite

Guest suite in Forest Lake

4.91 out of 5 average rating, 185 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

Cottage in Center City

4.99 out of 5 average rating, 101 reviews

3 Bed Lake House w/ Balconies

3 bedroom (2 king, 1 queen), 2 bath house located on South Center Lake. Soak in the beautiful view from the private balconies or from the wrap around deck! Enjoy provided snacks, bed side chocolates and a bag of coffee from the local roaster. During the summer months enjoy a fire by the lake (firewood provided), yard games (cornhole, croquet and horseshoes) or rent the pontoon. Free onsite laundry/gas grill/full kitchen utensils. Entrance on lower level is wheelchair accessible.

Guest favorite

Tiny home in Grantsburg

4.97 out of 5 average rating, 556 reviews

Snowshoe Creek & Little Wood Lake Tiny House

New 520 sf 'not too tiny' house on 20 wilderness acres. Year 'round fun. Dog friendly. RV & EV plug. Firepit. Your Snowshoe Creek and Little Wood Lake trails. Free canoe, kayak, paddleboat. $40/day mini-pontoon boat. Fishing. Internet. WiFi. AC. Gas Fireplace. Sleep by Number. Lovely bathroom. New gas stove. Ice maker. 2 TVs. 3 towns + Burnett Dairy/Bistro, 4 golf courses, DQ to fine dining, mini-golf, antiquing, multi-theater, Siren beach & 'Music in Park'. Wildlife! You'll return.

Guest favorite

Tiny home in Saint Croix Falls

4.9 out of 5 average rating, 155 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 front deck of our cozy cabin, as well as from the loft or many windows looking out. Enjoy the fire pit, private barrel sauna, gas grill, pond, 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!

Guest favorite

Cabin in Hudson

4.92 out of 5 average rating, 358 reviews

Cozy Cabin on Banks of Willow River (Burkhardt)

Our cozy cottage on the banks of the Willow River is ideally situated for enjoying the Willow River State Park experience while enjoying the comforts of home. Willow Falls is a short walk, and the main entrance is one mile from the front door. The cottage has a unique walk-in shower, luxurious tub, and full kitchen for your own use. The main master bedroom has a queen bed, barnboard walls, large windows, access to back deck & outdoor hottub. Two twin beds in front room sleep 2.

Guest favorite

Home in Taylors Falls

4.98 out of 5 average rating, 211 reviews

Maple House - Spacious 6 BR home for gatherings

ALL are welcome in private home above quaint village of Taylors Falls. Perfect for family stay-cations, vacations, groups & friends gatherings to relax or work. High speed wifi, cooking facilities, natural setting, fire pit, and private parking for 9 regular size cars. We follow Covid 19 enhanced cleaning guidelines with UV lights and HEPA filters on furnaces/air conditioners. Please reflect total number of guests in reservation.

Guest favorite

Rental unit in Amery

4.95 out of 5 average rating, 200 reviews

Serendipity Escape - Relax and enjoy nature!

Winter is here! So if you enjoy skiing, snowboarding, cross country skiing, or ice fishing. Just minutes away from Trollhaugen and Wild Mountain Ski resorts. Serendipity Escape on Lake Wapogasset! Available 365 for up to 4 guests, age 12 and older. Full Self Check-In. Fully equipped efficiency apartment with private entrance. Check out all our amenities provided for your convenience and perfect for a relaxing getaway.