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Compare 140 Vacation Homes in Osceola with updated reviews, rates, and availability.

Steps from Downtown Hudson Bars, Restaurants, and St. Croix River!
Living area

Steps from Downtown Hudson Bars, Restaurants, and St. Croix River!

10.0 out of 10, Exceptional, (28)
"We stayed the weekend of our daughter’s UWRF graduation. The amenities and “little touches” were so nice. Having the kitchen somewhat stocked was so nice. Also, the communication was amazing. Sheri was so quick to respond when a couple of issues came up - she even mailed us something that we forgot! Highly recommend this VRBO!"
Steps from Downtown Hudson Bars, Restaurants, and St. Croix River!
Modern Home
Living area

Modern Home

8.6 out of 10, Excellent, (28)
"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 651 total
includes taxes & fees
7 Jan - 8 January 2025
Modern Home
Cozy Lodge Theme Home in Beautiful Hudson, WI
Exterior

Cozy Lodge Theme Home in Beautiful Hudson, WI

9.8 out of 10, Exceptional, (62)
"Nice small home. Floors were not clean. Walking distance to many restaurant choices. "
Cozy Lodge Theme Home in Beautiful Hudson, WI
Cozy cottage in downtown Hudson, WI!
Private kitchen

Cozy cottage in downtown Hudson, WI!

10.0 out of 10, Exceptional, (133)
"My daughter and I stayed here for the weekend and it was lovely. The cottage is very clean and beautifully decorated for Christmas. Seamless process to check in/out and the house has everything you want or need for your stay. "
Cozy cottage in downtown Hudson, WI!
Stillwater's Third Street Inn
Winter MN. Only good picture I had. Waiting for things to bloom for new picture.

Stillwater's Third Street Inn

10.0 out of 10, Exceptional, (202)
"Great house for a weekend in Stillwater! Great location to walk downtown! Highly recommend! "
Stillwater's Third Street Inn
Beautiful Farmhouse Style Country Home with Indoor Pool!
Full sized in door pool

Beautiful Farmhouse Style Country Home with Indoor Pool!

10.0 out of 10, Exceptional, (39)
"Great place for a family vacation."
Beautiful Farmhouse Style Country Home with Indoor Pool!
Lake Home, hot tub, sauna, boat rental, private chef
Terrace/patio

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
House in quiet country, near lakes, snowmobile trail access, close to state park
Exterior

House in quiet country, near lakes, snowmobile trail access, close to state park

9.6 out of 10, Exceptional, (38)
"The kitchen lacked several items but luckily we came prepared because we knew we were planning on eating together. The towels were a little rough, however they were thick towels. Lots of space in the bedrooms and the bathrooms. The house was nice and clean. Disappointed that it had a fireplace, but a note hung on it saying not to use it. (It was below freezing outside and had snowed.)"
House in quiet country, near lakes, snowmobile trail access, close to state park
Hugo Home, Direct Lake Access & Private Dock!
Hugo Vacation Rental | 3BR | 2BA | 2 Steps for Entry | 1,300 Sq Ft

Hugo Home, Direct Lake Access & Private Dock!

10.0 out of 10, Exceptional, (14)
"We really enjoyed our stay. "
Hugo Home, Direct Lake Access & Private Dock!
A cozy home nestled in the heart of the river bluffs.
Front of Home - Main Keypad Entrance

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

10.0 out of 10, Exceptional, (5)
"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.
Lakefront Home with 6-person Hot Tub
Firepit on the beach

Lakefront Home with 6-person Hot Tub

The price is AED 988
AED 2,464 total
includes taxes & fees
13 Jan - 14 January 2025
Lakefront Home with 6-person Hot Tub
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Aerial view of the house & pole barn

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 387 total
includes taxes & fees
24 Dec - 25 Dec
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Living area

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

9.2 out of 10, Wonderful, (32)
"This is an older home but with many updates. Would have been a tight fit for 8 people, but was an excellent base camp for us while exploring the area. Host was responsive and helpful."
The price is AED 349
AED 666 total
includes taxes & fees
3 Jan - 4 January 2025
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Gathering families, friends, & coworkers
Former Lutheran Church remodeled into a vacation home

Gathering families, friends, & coworkers

9.8 out of 10, Exceptional, (29)
"Property manager was kind, communicative, and responsive to questions. Thoroughly cleaned. Tons of beds, private bedroom space, huge kitchen well stocked with equipment and dishes, and multiple large areas to hang out. We had ~35 people and there was tons of extra space. Clear Lake is a charming town, very small, with friendly locals and a grocery store in short walking distance. Just an hour from MSP airport as well. We had a wonderful time and intend to return when we come back through the...
Gathering families, friends, & coworkers
Historic Stillwater Home close to downtown
Exterior

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."
Historic Stillwater Home close to downtown
Cottage on the lake near downtown Stillwater

Cottage on the lake near downtown Stillwater

10.0 out of 10, Exceptional, (233)
"We had a great weekend! Thank you so much. "
The price is AED 1,900
AED 3,196 total
includes taxes & fees
5 Jan - 6 January 2025
Cottage on the lake near downtown Stillwater
St. Croix Riverview Home...Walking Distance to Downtown Stillwater
Ackerman Home

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

9.8 out of 10, Exceptional, (135)
"The overall experience was awesome. Very clean, very large house. Plenty of amenities inside the home that we could use... we cooked and baked while there and there were plenty of tools for that. They allowed both of our large breed dogs as long as they stayed on the main floor which wasn't a problem. The only thing I would change is that they were insistent on a face to face check in, which means we had to be there at a very specific time the first evening. Everything that we briefly discussed...
St. Croix Riverview Home...Walking Distance to Downtown Stillwater
Balsam Lake Cabin and Pickleball Retreat
Lake View from your Dock Area

Balsam Lake Cabin and Pickleball Retreat

9.4 out of 10, Exceptional, (27)
"The property is small, yet spacious and open! We didn't even make it downstairs to play games! Loved the layout of the house! Just a minor delay with the last bit of information, but it worked out at the end. We had a lovely stay!"
Balsam Lake Cabin and Pickleball Retreat
MINNeSTAY *Modern Chic | Host Christmas*
This modern tiny house kitchen has everything you need!

MINNeSTAY *Modern Chic | Host Christmas*

9.6 out of 10, Exceptional, (27)
"Highly recommend this place. Very clean and not overwhelming with decor. Super comfy and loved that most of the lights were dimmable. We would definitely book again in the future. "
MINNeSTAY *Modern Chic | Host Christmas*
Modern Lake Home!
Exterior

Modern Lake Home!

9.4 out of 10, Exceptional, (11)
"Great space and well equiped!"
The price is AED 1,469
AED 2,958 total
includes taxes & fees
24 Dec - 25 Dec
Modern Lake Home!
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 Beauty w Modern Updates Near Taylor's Falls
Living area

Historic Beauty w Modern Updates Near Taylor's Falls

10.0 out of 10, Exceptional, (24)
"5 friends getting"
The price is AED 606
AED 1,323 total
includes taxes & fees
5 Jan - 6 January 2025
Historic Beauty w Modern Updates Near Taylor's Falls
Hudson Inn & Suites
Front of property

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very Good, (680)
"This is an ok hotel. Nothing to get a 4.5 rating. We checked in on the Tuesday before Thanksgiving. We stayed 4 days. We were told breakfast would not be served because of the holidays. We understand 1 or two days. No breakfast all 4 days. Housekeeping not available till Friday. Seldom to never no one at front desk. If you just need a place to sleep this is the place."
The price is AED 285
AED 337 total
includes taxes & fees
24 Dec - 25 Dec
Hudson Inn & Suites
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

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

9.2 out of 10, Wonderful, (36)
"My sister and I only stayed for one night and used one of the rooms in the house but it was the perfect place to stay for the concert. The host, Steve, was very helpful and even drove us to and from the concert! Property is situated on a beautiful serene lot, hummingbirds were abundant out on the deck, had coffee and pastries in the am prior to checkout. Great spot!"
The price is AED 294
AED 387 total
includes taxes & fees
24 Dec - 25 Dec
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
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.