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Osceola Holiday Rentals

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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, (725)
"Nice clean quiet place to stay. "
The price is NZ$146
includes taxes & fees
14 July - 15 July
Hudson Inn & Suites

Gathering families, friends, & coworkers

9.8 out of 10, Exceptional, (34)
"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

Lakefront 2-bedroom log cabin on beautiful Horseshoe Lake with AC, WiFi

10.0 out of 10, Exceptional, (1)
"Cute property on a beautiful lake. My husband & I had 3 nights while our children were at camp so we stay here. We loved canoeing with our dog on the lake and seeing two loon families. The host was readily available for anything we needed. Cabin is clean & cute with two different living spaces in case you need some separation from family members, with lower level looking over the lake. There is a simple dock with a nice bench seat at the end where you can watch the lake/sunrise/sunset. We...
Lakefront 2-bedroom log cabin on beautiful Horseshoe Lake with AC, WiFi

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

9.2 out of 10, Wonderful, (41)
"Very peaceful and quiet. Plenty of private and shared spaces. Great communication and nearby pointers for food and recreation. Will be staying again!"
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

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

10.0 out of 10, Exceptional, (2)
"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,

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!"
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

Romantic getaway! With gorgeous views from the Hot Tub!

9.4 out of 10, Exceptional, (89)
"Everything was great! Highly recommended! Thank you!"
The price is NZ$533
includes taxes & fees
13 July - 14 July
Romantic getaway! With gorgeous views from the Hot Tub!

Lumberjack Inn 2300 sq.ft in DT with a rooftop

9.8 out of 10, Exceptional, (23)
"Great property to stay with friends. Location very convenient for shopping and restaurants. "
The price is NZ$1,257
includes taxes & fees
24 July - 25 July
Lumberjack Inn 2300 sq.ft in DT with a rooftop

All seasons cabin getaway

10.0 out of 10, Exceptional, (46)
"Was a great stay! We brought a boat and parked it at the dock for the entire stay... worked very well. Property is right there next to the lake and you're walking distance to several places to eat and drink."
All seasons cabin getaway

River road cabin

8.0 out of 10, Very good, (11)
"Me and some friends spent the night here during a weekend road trip. We loved the cozy interior, easy check-in and check-out process. The living room is spacious and the smart TV was a great thing to have. I would definitely recommend!"
The price is NZ$350
includes taxes & fees
21 July - 22 July
River road cabin

Lake Home property

10.0 out of 10, Exceptional, (5)
"Very nice, beautiful spot."
The price is NZ$471
includes taxes & fees
16 July - 17 July
Lake Home property

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 NZ$362
includes taxes & fees
21 July - 22 July
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

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

10.0 out of 10, Exceptional, (4)
"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.

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

10.0 out of 10, Exceptional, (71)
"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

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 NZ$612
includes taxes & fees
3 Aug - 4 Aug
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!

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

9.2 out of 10, Wonderful, (110)
"Was nice Jane checked on us. We enjoyed our stay! "
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin
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.
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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?

Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options: This holiday home rental outside of Osceola is located in a rural location, and has a patio, a BBQ 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.

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.