Book Holiday Homes in Osceola

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Featured Holiday Homes in Osceola

Steps from Downtown Hudson Bars, Restaurants, and St. Croix River!

Steps from Downtown Hudson Bars, Restaurants, and St. Croix River!

Hudson
Stay at this vacation home in Hudson. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Phipps Center for the Arts and Knoke's Chocolates ...
Steps from Downtown Hudson Bars, Restaurants, and St. Croix River!
Modern Home

Modern Home

Centuria
The price is NZ$314 per night from 7 Jan to 8 Jan
NZ$314
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this vacation home in Centuria. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Long Lake Park and Long Lake are located ...
Modern Home
Cozy Lodge Theme Home in Beautiful Hudson, WI

Cozy Lodge Theme Home in Beautiful Hudson, WI

Hudson
Stay at this vacation home in Hudson. Enjoy free WiFi, a garden, and patios. Popular attractions Phipps Center for the Arts and Knoke's Chocolates are located ...
Cozy Lodge Theme Home in Beautiful Hudson, WI
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Cozy cottage in downtown Hudson, WI!

Cozy cottage in downtown Hudson, WI!

Hudson
Stay at this vacation home in Hudson. Enjoy free WiFi, a garden, and patios. Popular attractions Phipps Center for the Arts and Knoke's Chocolates are located ...
Cozy cottage in downtown Hudson, WI!
Stillwater's Third Street Inn

Stillwater's Third Street Inn

Stillwater
Stay at this vacation home in Stillwater. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Ice Castle and Lowell Park are located ...
Stillwater's Third Street Inn
Beautiful Farmhouse Style Country Home with Indoor Pool!

Beautiful Farmhouse Style Country Home with Indoor Pool!

New Richmond
Book a stay at this family-friendly vacation home in New Richmond. Enjoy a garden, tennis courts, and patios. Popular attractions Splat Tag Paintball Park and ...
Beautiful Farmhouse Style Country Home with Indoor Pool!
Lake Home, hot tub, sauna, boat rental, private chef

Lake Home, hot tub, sauna, boat rental, private chef

Forest Lake
Book a stay at this family-friendly vacation home in Forest Lake. Enjoy a garden, a pool table, and patios. Popular attractions Clear Lake Park and Clear Lake ...
Lake Home, hot tub, sauna, boat rental, private chef
House in quiet country, near lakes, snowmobile trail access, close to state park

House in quiet country, near lakes, snowmobile trail access, close to state park

Hudson
Book a stay at this family-friendly vacation home in Hudson. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Willow River State Park ...
House in quiet country, near lakes, snowmobile trail access, close to state park
Hugo Home, Direct Lake Access & Private Dock!

Hugo Home, Direct Lake Access & Private Dock!

Hugo
Book a stay at this family-friendly vacation home in Hugo. Enjoy patios, cable/satellite TV service, and in-room washers/dryers. Popular attractions Centerville ...
Hugo Home, Direct Lake Access & Private Dock!
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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.

Osceola Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Osceola vacation homes are the perfect way for you to wing it.

Holiday houses in Osceola let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Osceola in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Osceola adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Osceola with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Osceola vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Osceola Holiday Homes essential information

Accommodation
140 Holiday Homes
Lowest Price
NZ$172
Highest Price
NZ$424
Popular accommodation
Steps from Downtown Hudson Bars, Restaurants, and St. Croix River! , Modern Home, Cozy Lodge Theme Home in Beautiful Hudson, WI, Cozy cottage in downtown Hudson, WI!, Stillwater's Third Street Inn, Beautiful Farmhouse Style Country Home with Indoor Pool!, Lake Home, hot tub, sauna, boat rental, private chef, House in quiet country, near lakes, snowmobile trail access, close to state park, Hugo Home, Direct Lake Access & Private Dock!

Top trending hotels in Osceola

River Valley Inn & Suites

River Valley Inn & Suites

2.5 out of 5
1030 N Cascade Street, Osceola, WI
Fully refundableReserve now, pay when you stay
The price is NZ$174 per night from 29 Dec to 30 Dec
NZ$174
includes taxes & fees
29 Dec - 30 Dec
Book a stay at this business-friendly motel in Osceola. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Riverwood Canoe and Osceola & ...
River Valley Inn & Suites
Hotel Crosby

Hotel Crosby

2.5 out of 5
232 Main St N, Stillwater, MN
Fully refundableReserve now, pay when you stay
The price is NZ$424 per night from 24 Dec to 25 Dec
NZ$424
includes taxes & fees
24 Dec - 25 Dec
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. ...
Hotel Crosby
Country Inn & Suites by Radisson, Forest Lake, MN

Country Inn & Suites by Radisson, Forest Lake, MN

2.5 out of 5
1954 West Broadway Avenue, Forest Lake, MN
Fully refundable
The price is NZ$183 per night from 1 Jan to 2 Jan
NZ$183
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this business-friendly hotel in Forest Lake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Country Inn & Suites by Radisson, Forest Lake, MN
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Best Western Plus White Bear Country Inn

Best Western Plus White Bear Country Inn

3 out of 5
4940 Highway 61 North, White Bear Lake, MN
Fully refundableReserve now, pay when you stay
The price is NZ$172 per night from 5 Jan to 6 Jan
NZ$172
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this hotel in White Bear Lake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the restaurant and the helpful staff in our reviews. ...
Best Western Plus White Bear Country Inn
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See all available properties in Osceola
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.