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Osceola Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals in Osceola

Our top choices for Osceola holiday rentals

Hudson Inn & Suites
Lobby

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very good, (758)
"Quite, clean & affordable "
The price is HK$576
HK$684 total
includes taxes & fees
27 Aug - 28 Aug
Hudson Inn & Suites
Gathering families, friends, & coworkers
Exterior

Gathering families, friends, & coworkers

9.8 out of 10, Exceptional, (36)
"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
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Exterior

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

9.6 out of 10, Exceptional, (35)
"We had a great stay!"
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Get away from it all and relax on the lake!
Property grounds

Get away from it all and relax on the lake!

9.8 out of 10, Exceptional, (174)
"Very clean and comfortable, secluded and cozy."
Get away from it all and relax on the lake!
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!
Outdoor dining

Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!

10.0 out of 10, Exceptional, (24)
"This is our third stay at the property. It is perfect for our family "
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!
All seasons cabin getaway
Terrace/patio

All seasons cabin getaway

10.0 out of 10, Exceptional, (48)
"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
Romantic getaway! With gorgeous views from the Hot Tub!
Exterior

Romantic getaway! With gorgeous views from the Hot Tub!

9.6 out of 10, Exceptional, (94)
"Peaceful, Romantic, and Quiet "
The price is HK$528
HK$2,060 total
includes taxes & fees
26 Aug - 27 Aug
Romantic getaway! With gorgeous views from the Hot Tub!
Beautiful, clear water lakefront 2-bedroom cabin on Horseshoe Lake pet friendly
Exterior

Beautiful, clear water lakefront 2-bedroom cabin on Horseshoe Lake pet friendly

10.0 out of 10, Exceptional, (6)
Beautiful, clear water lakefront 2-bedroom cabin on Horseshoe Lake pet friendly
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
Terrace/patio

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

9.4 out of 10, Exceptional, (44)
"Nice and spacious."
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
Lake Home property
Property grounds

Lake Home property

10.0 out of 10, Exceptional, (8)
"The Lake Home was perfect for my trip. The home was immaculate with more than enough space and accommodations. The location is private and quiet. Would definitely recommend, exceeds many higher priced locations!"
The price is HK$1,250
HK$2,218 total
includes taxes & fees
27 Aug - 28 Aug
Lake Home property
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Exterior

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

9.2 out of 10, Wonderful, (33)
"Lovely, cozy house. We enjoyed our stay!"
The price is HK$977
HK$1,699 total
includes taxes & fees
26 Aug - 27 Aug
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Historic Swedish Cottage on Quiet Lindstrom Lake
Exterior

Historic Swedish Cottage on Quiet Lindstrom Lake

9.4 out of 10, Exceptional, (219)
"Very homey, open spaces in home for a group to be together. Easy walk to interesting shops. Felt safe to take walks in. Beautiful lake side location."
The price is HK$2,884
HK$5,220 total
includes taxes & fees
2 Sept - 3 Sept
Historic Swedish Cottage on Quiet Lindstrom Lake
Dogs O.K Historic River Home: 6 Beds, 4 Bedrooms, 10 People,
Exterior

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

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

10.0 out of 10, Exceptional, (26)
"Clean and quiet "
Lucky View Lodge Log Cabin on Big Butternut Lake Luck, WI 3 acre 300ft lakeshore
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
Stovetop, dishwasher, paper towels

Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

10.0 out of 10, Exceptional, (6)
The price is HK$1,164
HK$1,906 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
Lumberjack Inn 2300 sq.ft in DT with a rooftop
Terrace/patio

Lumberjack Inn 2300 sq.ft in DT with a rooftop

9.6 out of 10, Exceptional, (32)
"Property was clean, welcoming, and well situated in downtown Stillwater. Rooftop seating area was awesome. Very responsive hosts. Will stay again!"
Lumberjack Inn 2300 sq.ft in DT with a rooftop
Private Suite in historic Stillwater North Hill
Interior

Private Suite in historic Stillwater North Hill

10.0 out of 10, Exceptional, (23)
"Highly recommend staying here"
The price is HK$938
HK$1,889 total
includes taxes & fees
26 Aug - 27 Aug
Private Suite in historic Stillwater North Hill
Spacious 4-bedroom house with private access to river in Willow River State Park
Property grounds

Spacious 4-bedroom house with private access to river in Willow River State Park

10.0 out of 10, Exceptional, (5)
"We stayed here based on the terrific location to Willow State Park. The property is gorgeous and you have so many areas to hike and explore including down to a really great stream. The owners were very attentive and they communicated well. Highly recommend this property!"
Spacious 4-bedroom house with private access to river in Willow River State Park
Beautiful Farmhouse Style Country Home with Indoor Pool!
Indoor pool

Beautiful Farmhouse Style Country Home with Indoor Pool!

10.0 out of 10, Exceptional, (51)
"We had a great time enjoying the house, including the pool, tennis courts, and fire ring!"
Beautiful Farmhouse Style Country Home with Indoor Pool!
Historic James Mulvey Carriage house (Whole house)
Pool

Historic James Mulvey Carriage house (Whole house)

9.8 out of 10, Exceptional, (29)
"Very nice accommodations within walking distance to town. Enjoyed our stay!"
The price is HK$3,900
HK$6,440 total
includes taxes & fees
2 Sept - 3 Sept
Historic James Mulvey Carriage house (Whole house)
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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Top Osceola Hotel Reviews

Royal Inn - Hudson I-94

Royal Inn - Hudson I-94

10/10 Excellent
"Property was clean. Rooms were clean and updated. Welcome bag with water and snacks at check-in! That was a wonderful surprise! "
Tami 2-night trip
Posted 2 days ago
Royal Inn - Hudson I-94

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 home, 5 single rooms, 2 adults 80/rm.: This holiday home rental outside of Osceola is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 5 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.