Book Holiday Homes in Osceola

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Featured Holiday Homes in Osceola

Charming 3-bedroom house 8 blocks from Historic Downtown Stillwater

Charming 3-bedroom house 8 blocks from Historic Downtown Stillwater

Stillwater
Located in Stillwater, this vacation home is within a 5-minute drive of Ice Castle and Stillwater Dog Park.
Charming 3-bedroom house 8 blocks from Historic Downtown Stillwater
Cozy Lodge Theme Home in Beautiful Hudson, WI

Cozy Lodge Theme Home in Beautiful Hudson, WI

Hudson
A stay at this vacation home places you in the heart of Hudson, within a 10-minute walk of Phipps Center for the Arts and Knoke's Chocolates.
Cozy Lodge Theme Home in Beautiful Hudson, WI
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

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

Houlton
The price is AU$171 per night from 30 Mar to 31 Mar
AU$171
includes taxes & fees
30 Mar - 31 Mar
Located in Houlton, this vacation home is in a rural location, within a 10-minute drive of Float Rite Park and Willow River State Park.
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
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Modern Lake Home!

Modern Lake Home!

White Bear Lake
Located in White Bear Lake, this vacation home is on a lake, within a 5-minute drive of Lakeshore Players Theatre and Maplewood Mall.
Modern Lake Home!
Cozy Lakefront 2 BR/1 BA Welcomes You!

Cozy Lakefront 2 BR/1 BA Welcomes You!

Lindstrom
Located in Lindstrom, this vacation home is on the waterfront, within a 15-minute drive of Green Lake and WineHaven Winery and Vineyard.
Cozy Lakefront 2 BR/1 BA Welcomes You!
Cozy cottage in downtown Hudson, WI!

Cozy cottage in downtown Hudson, WI!

Hudson
Located in Hudson, this vacation home is within a 5-minute drive of Knoke's Chocolates and Phipps Center for the Arts.
Cozy cottage in downtown Hudson, WI!
Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage

North Saint Paul
With a stay at this vacation home in North Saint Paul, you'll be within a 15-minute drive of Mississippi River and Century College.
Minne-GetAway: Modern Cottage
Location, Comfort, Amenities in Downtown Hudson, WI!!

Location, Comfort, Amenities in Downtown Hudson, WI!!

Hudson
With a stay at this vacation home, you'll be centrally located in Hudson, just a 4-minute walk from Knoke's Chocolates and 7 minutes by foot from Phipps Center ...
Location, Comfort, Amenities in Downtown Hudson, WI!!
Gathering families, friends, & coworkers

Gathering families, friends, & coworkers

Clear Lake
Located in Clear Lake, this vacation home is in a rural location, a 1-minute drive from Clear Lake Area Historical Museum and 8 minutes from Magnor Lake.
Gathering families, friends, & coworkers
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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
183 Holiday Homes
Lowest Price
AU$129
Highest Price
AU$317
Popular accommodation
Charming 3-bedroom house 8 blocks from Historic Downtown Stillwater, Cozy Lodge Theme Home in Beautiful Hudson, WI, Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options, Modern Lake Home! , Cozy Lakefront 2 BR/1 BA Welcomes You! , Cozy cottage in downtown Hudson, WI!, Minne-GetAway: Modern Cottage, Location, Comfort, Amenities in Downtown Hudson, WI!!, Gathering families, friends, & coworkers

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 AU$153 per night from 9 Apr to 10 Apr
AU$153
includes taxes & fees
9 Apr - 10 Apr
With a stay at River Valley Inn & Suites in Osceola, you'll be a 3-minute walk from Saint Croix River and within a 5-minute drive of Osceola & St. Croix Valley ...
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 AU$317 per night from 22 Apr to 23 Apr
AU$317
includes taxes & fees
22 Apr - 23 Apr
With a stay at Hotel Crosby in Stillwater, you'll be within a 5-minute walk of Ice Castle and Lowell Park.
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
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 13 Apr to 14 Apr
AU$151
includes taxes & fees
13 Apr - 14 Apr
Located in White Bear Lake, Comfort Inn & Suites St. Paul Northeast is within a 15-minute drive of Xcel Energy Center and University of Minnesota, Twin ...
Comfort Inn & Suites St. Paul Northeast
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AmericInn by Wyndham White Bear Lake St. Paul

AmericInn by Wyndham White Bear Lake St. Paul

2 out of 5
4675 White Bear Pkwy, White Bear Lake, MN
Fully refundableReserve now, pay when you stay
The price is AU$129 per night from 6 Apr to 7 Apr
AU$129
includes taxes & fees
6 Apr - 7 Apr
When you stay at AmericInn by Wyndham White Bear Lake St. Paul in White Bear Lake, you'll be near the beach, within a 15-minute drive of Xcel Energy Center and ...
AmericInn by Wyndham White Bear Lake St. Paul
Don't see what you're looking for?
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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.

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^Subject to availability and chosen travel dates.