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Compare 142 Vacation Homes in Osceola with updated reviews, rates, and availability.

Stillwater's Third Street Inn

10.0 out of 10, Exceptional, (205)
"Place has great location, very clean. The 4th bedroom is really just a bed on the enclosed porch. But was fine for us. Thank you."
Stillwater's Third Street Inn

Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!

10.0 out of 10, Exceptional, (10)
"This is our third stay at the property. It is perfect for our family "
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!

Blocks to Downtown. Charming 3 Bed, Entire House

10.0 out of 10, Exceptional, (61)
"Great location, nice house, very responsive host. "
Blocks to Downtown. Charming 3 Bed, Entire House

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

9.2 out of 10, Wonderful, (33)
"Everything was great. Just wish the location was more accurate when I booked. "
The price is AED 349
AED 659 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

A cozy home nestled in the heart of the river bluffs.

10.0 out of 10, Exceptional, (6)
"There were four adults in our group and we enjoyed our stay at this comfortable, conveniently located property. Great indoor/outdoor spaces. The location was perfect for walking to explore the historic downtown and to access the Lift bridge hiking trail. Zach was very quick to respond to my questions and also provided great recommendations for dining options and local attractions. Would definitely stay here again! "
A cozy home nestled in the heart of the river bluffs.

Modern Home

8.6 out of 10, Excellent, (29)
"We were in town for a church event. The owner was super accomodating to our constant changes. It was close to where we needed to be and had plenty of space. "
The price is AED 338
AED 647 total
includes taxes & fees
24 Feb - 25 Feb
Modern Home

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

10.0 out of 10, Exceptional, (138)
"The house was so cozy! We enjoyed the layout, the beds were so comfortable, and the house was decorated with Valentine’s Day decor with some extra goodies! Matthew was great to work with and the place had so many extras, including a few things I had forgotten, so that was a wonderful surprise! It snowed while we were there and Matthew shoveled/cleared snow right away. We love the Hudson area and would definitely stay here again!! Location is conveniently located to downtown, so that was a bonus...
Location, Comfort, Amenities in Downtown Hudson, WI!!

St. Croix Riverview Home...Walking Distance to Downtown Stillwater

9.8 out of 10, Exceptional, (136)
"Nice location. Pretty views. Great communication. No issues. Highly recommend. "
St. Croix Riverview Home...Walking Distance to Downtown Stillwater

Game Room! -Lakefront 5BRM -Close to Skiing and Trails

10.0 out of 10, Exceptional, (12)
"Beautiful home with a great setup. Lots for kiddos to do inside/during the winter. Host is very nice and great to communicate with. "
Game Room! -Lakefront 5BRM -Close to Skiing and Trails

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

10.0 out of 10, Exceptional, (57)
"This was a surprise stay to celebrate my wife’s 40th birthday. The view of the lake was breathtaking. The house was open, nicely maintained, and inviting. The private chef was wonderful. The hot tub was lovely. It was a delightful way to create a lasting experience that commemorates a milestone for someone so loved. "
Lake Home, hot tub, sauna, boat rental, private chef

Cozy cottage in downtown Hudson, WI!

10.0 out of 10, Exceptional, (135)
"We went for a weekend getaway and had a great time. Had a bunch of snow on Saturday and 8 below zero on Sunday but still had fun it this comfy place. Matt was awesome!! With any luck, we will be back next winter!!"
Cozy cottage 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

Charming and spacious 5 bedroom, 3 bath,19 guest home on peaceful keewahtin lake

9.8 out of 10, Exceptional, (28)
Charming and spacious 5 bedroom, 3 bath,19 guest home on peaceful keewahtin lake

Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.

9.6 out of 10, Exceptional, (33)
"We had a great stay!"
The price is AED 294
AED 388 total
includes taxes & fees
24 Feb - 25 Feb
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.

Beautiful Farmhouse Style Country Home with Indoor Pool!

10.0 out of 10, Exceptional, (40)
"What an amazing vacation! Beautiful home and wonderful pool. Great to get away from the cold!We hope to come back soon!"
Beautiful Farmhouse Style Country Home with Indoor Pool!

Home with Lake Access and 2023 Tri-toon available to rent

9.4 out of 10, Exceptional, (16)
"10 members of our family enjoyed another great weekend at this Vrbo. The space is comfortable for all."
Home with Lake Access and 2023 Tri-toon available to rent

Scandinavian Retreat

10.0 out of 10, Exceptional, (15)
"We recently had the pleasure of staying at the Scandinavian Retreat, and it was an absolutely delightful experience. "
The price is AED 643
AED 1,362 total
includes taxes & fees
24 Feb - 25 Feb
Scandinavian Retreat

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 AED 1,653
AED 2,257 total
includes taxes & fees
28 Feb - 1 Mar
Historic Stillwater Home close to downtown

Cozy Lodge Theme Home in Beautiful Hudson, WI

9.8 out of 10, Exceptional, (63)
"It was good to have a home base while we were in town visiting family. So many good places to eat close by. "
Cozy Lodge Theme Home in Beautiful Hudson, WI

Daffodil House - Large 6 Bedroom Accessible Rental

2.0 star property
10.0 out of 10, Exceptional, (1)
"was a great property- didn't realize it was a duplex, unsure if that was included. Still suited our needs, plenty of bedrooms, all large. "
The price is AED 1,219
AED 2,837 total
includes taxes & fees
24 Feb - 25 Feb
Daffodil House - Large 6 Bedroom Accessible Rental
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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Other property types in Osceola

Historic 1880s Home

10.0 out of 10, Exceptional, (58)
"Accurate listing, 5-10 min drive to Trollhaugen Skiing, 2 min walk from grocery store. Very clean and more than enough bathroom products, and a coffee machine!"
The price is AED 551
AED 690 total
includes taxes & fees
24 Feb - 25 Feb
Historic 1880s Home

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very Good, (688)
"I felt welcome and at home as soon as i walked through the door. "
The price is AED 285
AED 337 total
includes taxes & fees
9 Mar - 10 Mar
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
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.