Photo by rinchindorj

Search Cottages 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Osceola

Pet-friendly St Croix Falls Remote Retreat!
Interior

Pet-friendly St Croix Falls Remote Retreat!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Wonderful cozy retreat. "
Pet-friendly St Croix Falls Remote Retreat!
Quiet Farmhouse Retreat w/ Fire Pit - Pets Welcome
Interior

Quiet Farmhouse Retreat w/ Fire Pit - Pets Welcome

2.0 star property
Quiet Farmhouse Retreat w/ Fire Pit - Pets Welcome
'the Trailhouse at Serendipity' in Taylor Falls
Interior

'the Trailhouse at Serendipity' in Taylor Falls

3.0 star property
'the Trailhouse at Serendipity' in Taylor Falls
Cabin w/ Dock & Porch Across From Balsam Lake
Interior

Cabin w/ Dock & Porch Across From Balsam Lake

3.0 star property
Cabin w/ Dock & Porch Across From Balsam Lake
Hugo Home, Direct Lake Access & Private Dock!
Terrace/patio

Hugo Home, Direct Lake Access & Private Dock!

3.0 star property
Hugo Home, Direct Lake Access & Private Dock!
Historic Home in Taylors Falls w/ Patio & Fire Pit
Interior

Historic Home in Taylors Falls w/ Patio & Fire Pit

3.0 star property
Historic Home in Taylors Falls w/ Patio & Fire Pit
Lakefront Osceola Vacation Rental - Dogs Welcome!
Interior

Lakefront Osceola Vacation Rental - Dogs Welcome!

3.0 star property
Lakefront Osceola Vacation Rental - Dogs Welcome!
Family Home - Walk to Town & Balsam Lake!
Interior

Family Home - Walk to Town & Balsam Lake!

3.0 star property
Family Home - Walk to Town & Balsam Lake!
Picturesque Lake Elmo Cottage w/ Fire Pits!
Interior

Picturesque Lake Elmo Cottage w/ Fire Pits!

3.0 star property
Picturesque Lake Elmo Cottage w/ Fire Pits!
Wisconsin Vacation Rental w/ Fire Pit on Long Lake
Interior

Wisconsin Vacation Rental w/ Fire Pit on Long Lake

3.0 star property
Wisconsin Vacation Rental w/ Fire Pit on Long Lake
Spacious Luxury Cabin w/ Deck & Dock on Bone Lake
Interior

Spacious Luxury Cabin w/ Deck & Dock on Bone Lake

3.0 star property
Spacious Luxury Cabin w/ Deck & Dock on Bone Lake
'love Lake Retreat w/ Hot Tub in New Richmond!
Interior

'love Lake Retreat w/ Hot Tub in New Richmond!

3.0 star property
'love Lake Retreat w/ Hot Tub in New Richmond!
Cozy Balsam Lake Home: Deck, Private Dock + Kayaks
Interior

Cozy Balsam Lake Home: Deck, Private Dock + Kayaks

2.0 star property
Cozy Balsam Lake Home: Deck, Private Dock + Kayaks
Lake Wapogasset Home w/ Dock: 7 Mi to Amery
Interior

Lake Wapogasset Home w/ Dock: 7 Mi to Amery

3.0 star property
Lake Wapogasset Home w/ Dock: 7 Mi to Amery
4 Mi to Dtwn: White Bear Lake Home w/ Large Yard
Interior

4 Mi to Dtwn: White Bear Lake Home w/ Large Yard

3.0 star property
4 Mi to Dtwn: White Bear Lake Home w/ Large Yard
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
Sign in
Sign up, it's free

Top Osceola Hotel Reviews

Holiday Inn Express & Suites Hudson I-94 by IHG

Holiday Inn Express & Suites Hudson I-94 by IHG

10/10 Excellent
"Great place to stay "
James 5-night trip
Posted 10 hours ago
Holiday Inn Express & Suites Hudson I-94 by IHG

Frequently asked questions

Why book your cottage in Osceola with Expedia?
We think that a holiday should be a breeze, so if you're looking for cottages in Osceola at a great price, Expedia has got you covered. Stick to the budget and go for a wallet-friendly option far away from the downtown buzz, or splurge on a 5-star cottage to pamper your loved ones.
How can I find cheap cottages in Osceola?
With Expedia's convenient filter tool, locating cheap cottages in Osceola is a cinch. To discover stays that'll make your bank balance smile, tailor your search results by amenities, budget and star rating.
What is there to do in Osceola near my cottage?
The most useful travel accessory is a well-planned schedule. Osceola & St. Croix Valley Railway is an excellent place to start your exploration of Osceola.