Photo by rinchindorj

Holiday Rentals in Osceola

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Osceola

Walking Distance to the St. Croix River & Downtown

10.0 out of 10, Exceptional, (11)
"Stayed here while in the area for the Indian bike week."
Walking Distance to the St. Croix River & Downtown

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very good, (721)
"It was a pleasant stay"
The price is €75
includes taxes & fees
3 Jul - 4 Jul
Hudson Inn & Suites

Gathering families, friends, & coworkers

10.0 out of 10, Exceptional, (32)
"This was an amazing property for our large family to gather together to celebrate Christmas. There was plenty of sleeping, dining and gathering space."
Gathering families, friends, & coworkers

Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20

10.0 out of 10, Exceptional, (3)
"Quick was the only problem we had. Wish we had longer time!!! We will be bak for sure for all of next business trips to come to come this area !!! Thanks agian for everything "
Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20

Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

9.2 out of 10, Wonderful, (40)
"Very peaceful and quiet. Plenty of private and shared spaces. Great communication and nearby pointers for food and recreation. Will be staying again!"
The price is €94
includes taxes & fees
6 Jul - 7 Jul
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

Romantic getaway! With gorgeous views from the Hot Tub!

9.4 out of 10, Exceptional, (88)
"Clean and private"
The price is €230
includes taxes & fees
7 Jul - 8 Jul
Romantic getaway! With gorgeous views from the Hot Tub!

Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.

9.6 out of 10, Exceptional, (34)
"We had a great stay!"
The price is €94
includes taxes & fees
1 Jul - 2 Jul
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.

Cozy cabin on the lake

9.0 out of 10, Wonderful, (9)
"Very nice and quiet lake, a peaceful getaway"
Cozy cabin on the lake

Lumberjack Inn 2300 sq.ft in DT with a rooftop

9.8 out of 10, Exceptional, (22)
"Great property to stay with friends. Location very convenient for shopping and restaurants. "
The price is €611
includes taxes & fees
1 Jul - 2 Jul
Lumberjack Inn 2300 sq.ft in DT with a rooftop

Dogs O.K Historic River Home: 6 Beds, 4 Bedrooms, 10 People,

10.0 out of 10, Exceptional, (1)
"The location and property are perfect for a women's trip of hiking, shopping cute shops, wineries, and hanging out. Would stay again!"
Dogs O.K Historic River Home: 6 Beds, 4 Bedrooms, 10 People,

All seasons cabin getaway

10.0 out of 10, Exceptional, (44)
"Great location. Beautiful view. "
All seasons cabin getaway

Charming Underhill 2-bedroom cabin in lovely Center City with lake access.

10.0 out of 10, Exceptional, (3)
"Clean and cozy! Our family of 5 loved staying here. Great location and great host! "
Charming Underhill 2-bedroom cabin in lovely Center City with lake access.

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

9.2 out of 10, Wonderful, (33)
"Everything was great. Just wish the location was more accurate when I booked. "
The price is €191
includes taxes & fees
1 Jul - 2 Jul
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Northwoods Upscale Charming Lakefrt Bone Lk-4 Bedrm-Game Rm-BOOKING SUMMER 2026!

10.0 out of 10, Exceptional, (70)
"Beautiful place! VERY clean! 10/10 would stay here again. Spacious, fun game room, plenty of bathrooms! ;)"
Northwoods Upscale Charming Lakefrt Bone Lk-4 Bedrm-Game Rm-BOOKING SUMMER 2026!

Lucky View Lodge Log Cabin on Big Butternut Lake Luck, WI 3 acre 300ft lakeshore

10.0 out of 10, Exceptional, (24)
"Clean and quiet "
Lucky View Lodge Log Cabin on Big Butternut Lake Luck, WI 3 acre 300ft lakeshore

Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

9.2 out of 10, Wonderful, (109)
"Was nice Jane checked on us. We enjoyed our stay! "
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

Lodge at Lotus Lake

10.0 out of 10, Exceptional, (31)
"Had a wonderful time at this beautiful property! "
Lodge at Lotus Lake

Beautiful Farmhouse Style Country Home with Indoor Pool!

10.0 out of 10, Exceptional, (45)
"We had a great time enjoying the house, including the pool, tennis courts, and fire ring!"
Beautiful Farmhouse Style Country Home with Indoor Pool!

MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!

9.4 out of 10, Exceptional, (89)
"Close to everything... restaurants, shops, lift bridge and trails! Lots of space and cozy beds!"
The price is €320
includes taxes & fees
13 Jul - 14 Jul
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!

Lovely Lake House + WIFI + Coffee + Kayaks + Views

9.4 out of 10, Exceptional, (9)
"Pretty, relaxing"
Lovely Lake House + WIFI + Coffee + Kayaks + Views
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find a holiday rental in Osceola?

Yes, there are holiday rentals in Osceola close to Osceola & St. Croix Valley Railway, or you can select a more secluded option if you're looking for a relaxing stay. Osceola is known for its riverfront and bars. Make sure you have time to check out the waterfalls and entertainment choices during your trip.

What are some of the best holiday rentals that Osceola has to offer?

Lumberjack Inn 2300 sq.ft in DT with a rooftop: This holiday home rental outside of Osceola is located on a river, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Osceola?

Choose from 4 Expedia holiday rentals in Osceola for a memorable holiday.

What can I see and do in Osceola?

Saint Croix River and Apple River are a couple of lovely local spots to get outside and enjoy nature. Osceola & St. Croix Valley Railway and Trollhaugen are other places to visit while you're in town.

What are holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.