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
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 27 Cottages in Osceola with updated reviews, rates, and availability.

Historic James Mulvey Carriage house (Whole house)
Pool

Historic James Mulvey Carriage house (Whole house)

9.8 out of 10, Exceptional, (24)
"Very nice accommodations within walking distance to town. Enjoyed our stay!"
The price is AEDĀ 2,200
AEDĀ 3,492 total
includes taxes & fees
5 Jun - 6 Jun
Historic James Mulvey Carriage house (Whole house)
Sunset Point West facing cottage. Amazing spot RIGHT on the water!!!
Exterior

Sunset Point West facing cottage. Amazing spot RIGHT on the water!!!

9.8 out of 10, Exceptional, (54)
"This was such a cute little cabin. Please know that the pirmary bedroom is just a bed in a room without much room for anything else. This was more than fine for me. The view of the lake and sitting out of the dock was wonderful, beautiful, and relaxing. "
Sunset Point West facing cottage. Amazing spot RIGHT on the water!!!
Sunset Circle West facing waterfront Cottage
Terrace/patio

Sunset Circle West facing waterfront Cottage

9.6 out of 10, Exceptional, (45)
"Our second time at this property and just as good as the first! Very clean and welcoming. "
Sunset Circle West facing waterfront Cottage
Cozy Private Cottage overlooking the St. Croix River Valley
Aerial view

Cozy Private Cottage overlooking the St. Croix River Valley

10.0 out of 10, Exceptional, (162)
"This cottage was the perfect place for our ā€œHallmark Weekend ā€œ in Stillwater! The location was perfect as we were easily able to enjoy all of the dining, shopping, and holiday festivities of this charming community!"
Cozy Private Cottage overlooking the St. Croix River Valley
Picturesque Lake Elmo Cottage w/ Fire Pits!
Interior

Picturesque Lake Elmo Cottage w/ Fire Pits!

9.8 out of 10, Exceptional, (6)
"This was my first VRBO experience and it was amazing. The place was extra clean, spacious and very comfortable. It was so beautiful inside and out, with lots of wonderful touches and our host was very helpful and welcoming. "
Picturesque Lake Elmo Cottage w/ Fire Pits!
Incredible Lake Views Only Steps Away from The Water
3 bedrooms, desk, iron/ironing board, travel crib

Incredible Lake Views Only Steps Away from The Water

9.6 out of 10, Exceptional, (27)
"great spot,would love to come in summer"
Incredible Lake Views Only Steps Away from The Water
Park Place Cottage
Exterior

Park Place Cottage

9.8 out of 10, Exceptional, (25)
"Restful stay, comfortable beds clean home. Would stay again. "
Park Place Cottage
Cozy Lakeside Cottage
Beach

Cozy Lakeside Cottage

8.8 out of 10, Excellent, (18)
"Overall great place and location"
Cozy Lakeside Cottage
Lakefront Cottage 2 min to downtown
Smart TV, books, stereo

Lakefront Cottage 2 min to downtown

10.0 out of 10, Exceptional, (22)
"Cute cottage, beautiful view, great hosts."
Lakefront Cottage 2 min to downtown
Cozy Lake Elmo Cottage
Fridge, microwave, oven, stovetop

Cozy Lake Elmo Cottage

10.0 out of 10, Exceptional, (17)
"Everything was great and exactly as listed. "
Cozy Lake Elmo Cottage
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, (1)
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
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!
Cabin w/ Dock & Porch Across From Balsam Lake
Terrace/patio

Cabin w/ Dock & Porch Across From Balsam Lake

3.0 star property
Cabin w/ Dock & Porch Across From Balsam Lake
Charming Taylors Falls Home w/ Deck, Fire Pit
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Taylors Falls Home w/ Deck, Fire Pit

3.0 star property
Charming Taylors Falls Home w/ Deck, Fire Pit
Wisconsin Vacation Rental w/ Fire Pit on Long Lake
House (4 Bedrooms) | Interior

Wisconsin Vacation Rental w/ Fire Pit on Long Lake

3.0 star property
Wisconsin Vacation Rental w/ Fire Pit on Long Lake
Lakefront Osceola Vacation Rental - Dogs Welcome!
TV, fireplace, books

Lakefront Osceola Vacation Rental - Dogs Welcome!

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

Historic Home in Taylors Falls w/ Patio & Fire Pit

3.0 star property
Historic Home in Taylors Falls w/ Patio & Fire Pit
Cozy Balsam Lake Home: Deck, Private Dock + Kayaks
Exterior

Cozy Balsam Lake Home: Deck, Private Dock + Kayaks

2.0 star property
Cozy Balsam Lake Home: Deck, Private Dock + Kayaks
Spacious Luxury Cabin w/ Deck & Dock on Bone Lake
Fireplace, books

Spacious Luxury Cabin w/ Deck & Dock on Bone Lake

3.0 star property
Spacious Luxury Cabin w/ Deck & Dock on Bone Lake
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

Frequently asked questions

Why book your cottage in Osceola with Expedia?
We think that a vacay should be a breeze, so if youā€™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 Expediaā€™s convenient filter tool, locating cheap cottages in Osceola is a cinch. To discover stays thatā€™ll make your bank balance smile, tailor your search results by amenities, budget and star rating.