Photo by rinchindorj

Search Vacation Homes in Osceola

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 185 Vacation Homes in Osceola with updated reviews, rates, and availability.

Charming 3-bedroom house 8 blocks from Historic Downtown Stillwater

10.0 out of 10, Exceptional, (2)
"Very comfortable and clean in a convenient location "
Charming 3-bedroom house 8 blocks from Historic Downtown Stillwater

Cozy Lodge Theme Home in Beautiful Hudson, WI

9.8 out of 10, Exceptional, (66)
"Lovely little spot just a few blocks from downtown Hudson. It was the perfect place for a couples getaway with my husband."
Cozy Lodge Theme Home in Beautiful Hudson, WI

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

9.2 out of 10, Wonderful, (37)
"Very peaceful and quiet. Plenty of private and shared spaces. Great communication and nearby pointers for food and recreation. Will be staying again!"
The price is SAR 300
SAR 396 total
includes taxes & fees
9 Apr - 10 Apr
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

Modern Lake Home!

9.4 out of 10, Exceptional, (12)
"Super comfortable with beautiful views of the lake. We loved that its on a cul-de-sac so no traffic... its quite neighbors are nice and an overall fabulous place to unwind... we would DEFINITELY stay here again"
The price is SAR 751
SAR 2,067 total
includes taxes & fees
21 Apr - 22 Apr
Modern Lake Home!

Cozy Lakefront 2 BR/1 BA Welcomes You!

9.8 out of 10, Exceptional, (50)
"We loved this little cabin with a lake view. It was perfect for us being in town for the weekend visiting our son. Loved it!"
Cozy Lakefront 2 BR/1 BA Welcomes You!

Cozy cottage in downtown Hudson, WI!

10.0 out of 10, Exceptional, (139)
"It’s a cozy tiny house in a quiet neighborhood. Well stocked with essential toiletries, cookware, and bedding. Stayed 2 nights and was not dissatisfied with anything!! "
Cozy cottage in downtown Hudson, WI!

Minne-GetAway: Modern Cottage

9.6 out of 10, Exceptional, (5)
"Very nice"
The price is SAR 201
SAR 882 total
includes taxes & fees
14 Apr - 15 Apr
Minne-GetAway: Modern Cottage

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

10.0 out of 10, Exceptional, (142)
"Property was clean, quiet, and easy to access and use. Thanks for a smooth process and a great experiance!"
Location, Comfort, Amenities in Downtown Hudson, WI!!

Gathering families, friends, & coworkers

10.0 out of 10, Exceptional, (32)
"We had a great stay in Clear Lake. The house was big enough to comfortably fit our large extended family and the location was close to the everything. The beds were comfy, the kitchen was well equipped for large meals, and the gathering areas were perfect for our group. We will definitely stay again!! "
Gathering families, friends, & coworkers

Secluded Lakefront Home with outdoor hot tub, fire pit & indoor Hockey Rink

10.0 out of 10, Exceptional, (45)
"It was gorgeous, clean, open and quick communication with host. "
Secluded Lakefront Home with outdoor hot tub, fire pit & indoor Hockey Rink

Cottage on the lake near downtown Stillwater

10.0 out of 10, Exceptional, (233)
"We had a great weekend! Thank you so much. "
Cottage on the lake near downtown Stillwater

Stillwater's Third Street Inn

10.0 out of 10, Exceptional, (206)
"The home was beautiful and clean. The owner was very kind and accommodating! "
Stillwater's Third Street Inn

Get away from it all and relax on the lake!

9.8 out of 10, Exceptional, (160)
"Very clean and comfortable, secluded and cozy."
Get away from it all and relax on the lake!

Gorgeous 5 bed Remodel near Downtown Hudson for Groups!

10.0 out of 10, Exceptional, (5)
"My friends and I had a blast at the house! Lots of amazing memories!!! Plenty of room, very clean, close to lots of bars and restaurants. Couldn’t be happier!"
The price is SAR 3,674
SAR 4,553 total
includes taxes & fees
20 Apr - 21 Apr
Gorgeous 5 bed Remodel near Downtown Hudson for Groups!

Beautiful Farmhouse Style Country Home with Indoor Pool!

10.0 out of 10, Exceptional, (41)
"This house has it all: comfortable beds, beautiful and clean rooms, and a truly amazing indoor pool! Our group (5 8-year old girls and their moms) had a blast! It was a very memorable weekend! "
Beautiful Farmhouse Style Country Home with Indoor Pool!

Historic Stillwater Home close to downtown

10.0 out of 10, Exceptional, (37)
"We thoroughly enjoyed our stay for a guys night out in Stillwater. The house was in a quiet neighborhood and came fully stocked. Great communication and easy check in. Highly recommended."
The price is SAR 939
SAR 1,396 total
includes taxes & fees
15 Apr - 16 Apr
Historic Stillwater Home close to downtown

Historic Beauty w Modern Updates Near Taylor's Falls

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay at this early 1900’s era home. Our children enjoyed exploring all the nooks and closets playing with all the toys they brought while us adults enjoyed great conversation by the fire and playing games in the dining room. It was quite chilly during our stay (average temps below zero the entire time) but the house was quite comfortable with plenty of extra blankets if one wanted. We used the hot tub a few shorts times due to the temps but was a nice retreat to get some fresh...
The price is SAR 620
SAR 1,353 total
includes taxes & fees
10 Apr - 11 Apr
Historic Beauty w Modern Updates Near Taylor's Falls

Riverfront cabin with kayaks and canoes

9.8 out of 10, Exceptional, (107)
"Enjoyed our stay with 3 generations. Checked out the Pumpkin Train out of Osceola and visited the Amery farmers markets and parks. Neighborhood has lots of fun animal spotting for the kids. Loved the huge kitchen and the loft is well equipped with kids toys and"
Riverfront cabin with kayaks and canoes

Serene Suburban Retreat with Hot Tub next to the Super Rink, 3M Open and USA Cup

Serene Suburban Retreat with Hot Tub next to the Super Rink, 3M Open and USA Cup

Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

9.2 out of 10, Wonderful, (107)
"I rented this home for a sisters getaway. It really is a great space for a relaxing weekend. My sisters noted that the shower curtains had pink mold and the grout needed a good cleaning, thus the 4 stars. The kitchen was well stocked, although the knives could be better with more variety. I would rent again!"
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin
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.
Don't see what you're looking for?
See all available properties in Osceola
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Osceola

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very Good, (694)
"The place was very clean . The sheets were really nice and the pillows were amazing. Very nice staff at front desk."
The price is SAR 291
SAR 345 total
includes taxes & fees
22 Apr - 23 Apr
Hudson Inn & Suites

Gathering families, friends, & coworkers

10.0 out of 10, Exceptional, (32)
"We had a great stay in Clear Lake. The house was big enough to comfortably fit our large extended family and the location was close to the everything. The beds were comfy, the kitchen was well equipped for large meals, and the gathering areas were perfect for our group. We will definitely stay again!! "
Gathering families, friends, & coworkers

Lumberjack Inn 2300 sq.ft in DT with a rooftop

10.0 out of 10, Exceptional, (15)
"If you are looking for a beautiful place to stay that is right on Main Street, book this vrbo. We had our girls weekend/bridal celebration here and it was the perfect!!! The hosts communicated efficiently and it was super easy to get around Stillwater because everything is within walking distance. Thanks again for an awesome weekend, highly recommend!! "
The price is SAR 976
SAR 2,437 total
includes taxes & fees
10 Apr - 11 Apr
Lumberjack Inn 2300 sq.ft in DT with a rooftop
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.