Osceola, WI

Travel Guide

A waterfall cascading over a rocky cliff surrounded by lush greenery.
A waterfall cascading over rocks in a forested area.
A waterfall in a forested area with a rocky stream below.
A golf course with ponds and autumn-colored trees.
River Valley Inn & Suites

River Valley Inn & Suites

2.5 out of 5
1030 N Cascade Street Osceola WI
$80 nightly
The price is $88 total per night from Nov 1 to Nov 2
$88 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly motel in Osceola. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Riverwood Canoe and Osceola & ...
7.8/10 Good! (521 reviews)
"Very clean and great staff. Breakfast was awesome!"

Reviewed on Oct 24, 2026

River Valley Inn & Suites
Hotel Crosby

Hotel Crosby

2.5 out of 5
232 Main St N Stillwater MN
$234 nightly
The price is $262 total per night from Nov 25 to Nov 26
$262 total
Nov 25 - Nov 26
Total with taxes and fees
Stay at this hotel in Stillwater. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the restaurant and the helpful staff in our reviews. ...
9.6/10 Exceptional! (1,003 reviews)
"The rooftop patio with hot tub was worth every penny!! The food at the onsite restaurant was absolutely the best!! Highly recommend this hotel!!!"

Reviewed on Oct 25, 2026

Hotel Crosby
Comfort Inn & Suites St. Paul Northeast

Comfort Inn & Suites St. Paul Northeast

2.5 out of 5
3505 Vadnais Center Dr. White Bear Lake MN
$98 nightly
The price is $107 total per night from Nov 11 to Nov 12
$107 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in White Bear Lake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Comfort Inn & Suites St. Paul Northeast
See all 494 properties in Osceola
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hudson Inn & Suites

Hudson Inn & Suites

3 out of 5
811 Dominion Drive Hudson WI
Book a stay at this business-friendly aparthotel in Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hudson Inn & Suites
Gathering families, friends, & coworkers

Gathering families, friends, & coworkers

Clear Lake WI
Stay at this vacation home in Clear Lake. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Clear Lake Area Historical Museum and Apple River ...
9.8/10 Exceptional! (44 reviews)
"Another fantastic training trip for our team! We love coming because it's such a comfortable space that can accommodate everyone in our group. Thank you!!"

Reviewed on Aug 31, 2026

Gathering families, friends, & coworkers
Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill

Stillwater MN
Stay at this apartment in Stillwater. Enjoy free WiFi, a garden, and patios. Popular attractions Warden's House Museum and Lowell Park are located nearby.
10/10 Exceptional! (51 reviews)
"I was pleased. Everything was accurate to the advertisement."

Reviewed on Oct 20, 2026

Private Suite in historic Stillwater North Hill
See all properties in Osceola
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Osceola attractions

Osceola & St. Croix Valley Railway

8.6/10 (14 reviews)
Enjoy a stop at Osceola & St. Croix Valley Railway, an entertaining place to visit in Osceola. Discover the waterfalls in this relaxing area.
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Frequently asked questions

Is Osceola worth visiting?
Osceola is worth visiting for its unique attractions, including the Osceola & St. Croix Valley Railway, and the natural beauty of Farmington Bottoms State Natural Area. Travelers can also enjoy diverse dining experiences, with options ranging from Italian to North American cuisine.
When is the best time to visit Osceola?
The best time to visit Osceola is from July through September. For travelers seeking a more relaxed experience with fewer crowds and potentially better value, the quieter months of November through January are a good option.
What is Osceola known for?
Osceola is known for the Osceola & St. Croix Valley Railway, offering scenic experiences. Travelers can also explore the Farmington Bottoms State Natural Area and enjoy activities with Riverwood Canoe. The city also features a presence of Italian food culture.
What is a good itinerary length for Osceola?
A good itinerary length for Osceola is two to three days to experience the Osceola & St. Croix Valley Railway and explore Farmington Bottoms State Natural Area. An extended stay of four to five days allows for more time to enjoy a Riverwood Canoe trip and sample the local Italian, North American, and Latin American dining options.
What are the top things to do in and around Osceola?
Osceola offers scenic railway rides, natural area exploration, and tranquil lakes for travelers to enjoy:

  • Ride the Osceola & St. Croix Valley Railway for a scenic journey.
  • Explore the natural beauty of Farmington Bottoms State Natural Area.
  • Go canoeing from the landmark Riverwood Canoe.
  • Visit Big Lake for outdoor recreation and relaxation.
  • Discover the serene waters of Rice Lake.

How do I plan a trip to Osceola?
To plan your trip to Osceola, search for places to stay on Expedia and book flights in advance. Consider a rental car to visit attractions like Osceola & St. Croix Valley Railway, Farmington Bottoms State Natural Area, and Riverwood Canoe. When planning activities, remember to pair outdoor options with indoor backups for weather flexibility.
What cuisines can you find in Osceola?
In Osceola you can find Italian cuisine, offering dishes such as pasta, pizza, lasagna, and risotto. Travelers also have options for North American fare, Latin American cuisine with Mexican influences, Asian dishes, and Mediterranean specialties.
Can I book a refundable hotel in Osceola?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Osceola by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Osceola with Expedia?
Expedia makes it easier to plan your Osceola trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Osceola?
The best choice depends on your travel style. Hotels in Osceola can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Osceola trip on Expedia?
Once you've booked your Osceola trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Osceola trip?
Expedia offers customer support before, during, and after your Osceola trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Osceola?
If it's your first trip to Osceola, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Osceola hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Osceola hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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