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

The treehouse is nestled among the branches of a large oak tree, showcasing a rustic wooden exterior. A spacious deck wraps around the structure, offering glimpses of the surrounding foliage and natural beauty.

Home in Cottage Grove

4.98 out of 5 average rating, 686 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

The entrance features a welcoming path leading to double doors framed by greenery. Potted flowers and shrubs line the walkway, contributing to the vibrant garden. The structure's two-level porch, adorned with chairs and hanging plants, offers an inviting outdoor space.

Home in Whittier

4.93 out of 5 average rating, 40 reviews

Sweet retreat in fantastic uptown close to lakes.

Your family will be close to everything when you stay at this centrally-located place. Trendy Uptown location just steps away from numerous culinary and entertainment options. With a brand new gourmet lovers full kitchen, Large dinning room and living room. There is plenty of space to sprawl out and work or play in this historic home. Enjoy the long front porch out front, or the private back patio. Enjoy your morning coffee on a small private porch just off of the kitchen. Top quality amenities

Top guest favorite

A modern bathroom is showcased with a sleek white sink and illuminated mirror. Neutral gray tiles adorn the walls, while a wooden door labeled 'POWDER ROOM' creates a stylish focal point. Towels and toiletries are neatly arranged on a shelf above the sink.

Guesthouse in Whittier

4.99 out of 5 average rating, 603 reviews

Luxury Urban Retreat

Designer Carriage Home with all the modern amenities and a true place to relax and unwind. With a "walkscore" of 94 this beautiful newly renovated studio is walker's paradise ! Central AC / Heat, dedicated High Speed WIFI, luxury bedding, a King Sized Bed and a European Spa like bathroom are just a few of the amenities you will come to enjoy and appreciate. Equipped with Keurig Coffee Maker, Toaster, Refrigerator and Microwave this will easily feel like home. Reserved Garage Parking included.

Top guest favorite

A wooden deck is visible, featuring two patterned chairs that overlook a green backyard. Nearby, neighboring houses with a mix of rooftops and greenery can be seen, alongside a small patio area with an umbrella. The sky displays a mix of clouds and sunlight.

Apartment in Minneapolis

4.97 out of 5 average rating, 173 reviews

The Lott Nest; A Hideaway in the City

Kick back and relax in this open concept, tree top bungalow. Feel at peace nestled in the tree tops. Designed with stylish eco-conscious details in mind, this recently renovated unit boasts a new bathroom and upcycled kitchen. There is a sweet lil den and 2 bistro decks to enjoy morning coffee and a glass of vino at night. The king sized bed is nearly tucked into the trees, so you’ll get the best nights of rest! Restaurants and stores within walking distance! Owner occupied first floor unit:)

Top guest favorite

A charming house with a steep, gabled roof is framed by natural stone landscaping. A pathway made of pavers leads to the front porch, surrounded by trees and seasonal vegetation. Large windows allow for plenty of natural light, creating an inviting exterior.

Home in Wayzata

5 out of 5 average rating, 29 reviews

Charming Wayzata Cottage

Step into a welcoming haven where comfort & style intertwine. Enjoy a spacious living room with abundant seating, a modern kitchen, and comfortable bedrooms with fresh linens. Outside, a landscaped yard & a cozy front porch provide a slice of paradise. Conveniently located in a peaceful neighborhood next to Lake Minnetonka, you're just a short walk from downtown Wayzata, offering adorable shops, delicious dining, & more. Enjoy a stay that blends relaxation & recreation in a delightful setting.

Guest favorite

A rustic cabin is seen illuminated against the backdrop of tall trees at twilight. A winding gravel path leads to the cabin's entrance, showcasing its warm glow through the large window and inviting porch.

Place to stay in Trego

4.89 out of 5 average rating, 47 reviews

Heart's Rest

Heart's Rest is a rustic lodging experience in the heart of Northern Wisconsin. Two hours from the Twin Cities, one hour from Duluth & Bayfield. A great location for nearby villages' shopping , eateries, wineries, entertainment & events. Or ground yourself at the cabin & just relax! This airy retreat creates opportunities for lovers. families, & good friends to gather and have fun! Bring an ATV, snowmobile, snowshoes, fishing pole, fur baby, a shopping bag, a great book & a favorite recipe!

Top guest favorite

The living room features a spacious gray sectional sofa complemented by a wooden coffee table. Accent chairs are positioned nearby, and natural light fills the space through a large window. Decorative wall art and plants enhance the inviting atmosphere.

Home in Chanhassen

5 out of 5 average rating, 13 reviews

Perfect Gathering Spot | Spacious & Comfy Home

A perfect home for gathering with friends and family! 4 spacious bedrooms (1 king, 2 queens, 2 twins) and 2 full bathrooms. Queen blow-up bed + full size futon for up to 10 guests. Large deck, gas grill, fire pit, private fenced-in yard, stocked kitchen - everything you need for a GREAT stay! Convenient location: 4 min from Dinner Theater, 5 mins from Lake Ann, 6 mins from Excelsior! Target, Starbucks, Caribou Coffee and multiple grocery stores all within a 5 min drive! PERMIT #: PZ24-0077

Guest favorite

An aerial view of a spacious home set among trees, with a river visible in the background. The outdoor patio can be seen, along with a bonfire pit. The surrounding landscape showcases a mix of greenery and bare trees, indicating the winter season.

Home in Prescott

4.89 out of 5 average rating, 46 reviews

Whispering Pines: rivertown getaway

Skiing and snowmobiling just minutes away! This home is located very close to the River (although not visible through the trees) on a dead-end road in the rural countryside a few miles South of Prescott. There is enough seclusion that, even in winter, when the trees have dropped their leaves, it is difficult to see any neighboring houses. The town of Prescott is only a six-minute drive away (please note posted speed limits, which are often overlooked, but strictly enforced).

Top guest favorite

A living room is depicted with a light-colored sofa, accented by colorful throw pillows. Natural light filters through multiple windows, highlighting hardwood floors. The adjacent dining area features a wooden table surrounded by chairs, enhancing the open and inviting layout.

Home in Saint Paul

5 out of 5 average rating, 211 reviews

Classic, quiet, large 2-BR, near Macalester Coll.

“Stop looking…this is it.” “immaculate, homey and spacious” Six stars for this place!.” NO CLEANING FEE! Our place is close to 5 colleges, public transportation, historic Summit Avenue, Grand Avenue with its wonderful shops and restaurants, both downtowns, and is an easy 12-15 minute drive from the airport, MSP. You’ll love the location, the size and the quiet charm, AND we are rated SUPERHOSTS! Our place is good for families, couples, small groups and business travelers.

Guest favorite

Home in Bay City

4.94 out of 5 average rating, 17 reviews

Isabelle Creek Haven - Ultimate Group Getaway

Welcome to our stunning house on Isabelle Creek in Esdaile, WI! Once a historic barn, this beautifully restored home offers the ultimate group getaway with its massive open floor plan and luxurious amenities. The expansive living area is perfect for entertaining, with plenty of space for everyone to relax and enjoy each other's company. The fully equipped kitchen is a chef's dream, with high-end appliances and plenty of counter space to prepare gourmet meals for your group.

Top guest favorite

Condo in Nokomis

4.97 out of 5 average rating, 545 reviews

Bright City Condo Near the Light Rail

Welcome to my delightfully curated condo in the heart of the Twin Cities! This bright and happy home is the perfect spot for an amazing visit to the city. The location of my condo is unbeatable - just a few light-rail stops from the airport and within walking distance to Minnehaha Falls. If you're new to Airbnb or cannot instantly book, please don't hesitate to introduce yourself - we would love to host you and ensure an unforgettable stay in the Twin Cities.

Guest favorite

An open-concept living area features a round wooden dining table surrounded by black chairs. Natural light floods the space, highlighting the exposed beams and white cabinetry in the kitchen area. Fresh greenery is displayed on the table, complementing the warm wooden floors.

Home in Wayzata

4.9 out of 5 average rating, 29 reviews

Cozy cottage in downtown Wayzata - walk to lake!

Welcome to our beautiful and family-friendly cottage centrally located in downtown Wayzata just a short walk to Lake Minnetonka. Wayzata is a safe, fun, and relaxing community full of delicious restaurants, outdoor activities, and wonderful shops. You’ll have easy, walking access to anything you desire to experience in our lakeside town while also having a private, cozy space to return to in a quiet and peaceful neighbourhood.