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Holiday Homes in Osceola

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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Featured Holiday Homes in Osceola and around

Stillwater's Third Street Inn
Property grounds

Stillwater's Third Street Inn

10.0 out of 10, Exceptional, (204)
"I booked this house for my wedding weekend and it was perfect! It’s very close to the JX Venue space that you can walk to and from. The house was clean and plenty of room for everyone. It’s within walking distance of Main Street and all the bars and restaurants. The communication with the owners was easy and they were helpful with explaining all the rules. I would recommend this place for a fun weekend stay in Stillwater! "
Stillwater's Third Street Inn
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!
Outdoor dining

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

10.0 out of 10, Exceptional, (9)
"This was a great location for our staff retreat. Lots of space for group meetings, while allowing private time in our rooms. Beautiful location and lovely accomodations."
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!
Blocks to Downtown. Charming 3 Bed, Entire House
Fridge, microwave, oven, stovetop

Blocks to Downtown. Charming 3 Bed, Entire House

10.0 out of 10, Exceptional, (59)
"Groom and groomsmen stayed before wedding at JX. Close, convenient and host was very accommodating!"
Blocks to Downtown. Charming 3 Bed, Entire House
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Exterior

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 €176
includes taxes & fees
27 Jan - 28 Jan
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Modern Home
Exterior

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 €172
includes taxes & fees
28 Jan - 29 Jan
Modern Home
Location, Comfort, Amenities in Downtown Hudson, WI!!
Exterior

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

10.0 out of 10, Exceptional, (135)
"The house was perfect! Host was very responsive. We loved the location of the house. It was close to everything. It had all the amenities we needed. Bed was comfortable. "
Location, Comfort, Amenities in Downtown Hudson, WI!!
A cozy home nestled in the heart of the river bluffs.
Interior

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

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

9.8 out of 10, Exceptional, (136)
"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
Lake Home, hot tub, sauna, boat rental, private chef

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

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
Cozy cottage in downtown Hudson, WI!
Outdoor dining

Cozy cottage in downtown Hudson, WI!

10.0 out of 10, Exceptional, (135)
"I’m from Hudson and planned a visit for my birthday. This place was perfect for my stay! "
Cozy cottage in downtown Hudson, WI!
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Exterior

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 €105
includes taxes & fees
26 Jan - 27 Jan
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Gathering families, friends, & coworkers
Exterior

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
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."
The price is €600
includes taxes & fees
31 Jan - 1 Feb
Historic Stillwater Home close to downtown
Beautiful Farmhouse Style Country Home with Indoor Pool!
Indoor 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!
Balsam Lake Cabin and Pickleball Retreat
Pool

Balsam Lake Cabin and Pickleball Retreat

9.4 out of 10, Exceptional, (28)
"This property was a great place for 3 generations at Christmas time. Spacious and comfortable and great communication."
Balsam Lake Cabin and Pickleball Retreat
Spacious lakeside retreat
Dining

Spacious lakeside retreat

10.0 out of 10, Exceptional, (34)
"Very Clean, Big spaces, Lots to do. Perfect place for meeting extended family. "
Spacious lakeside retreat
MINNeSTAY *Modern Chic | Host Christmas*
Fridge, microwave, oven, stovetop

MINNeSTAY *Modern Chic | Host Christmas*

9.6 out of 10, Exceptional, (28)
"We were in the area celebrating the holidays with family. We chose this location as a central hub with easy access to family, shopping, and eateries. The home was clean and the layout provided comfortable individual and shared gathering spaces. The property management and maintenance team quickly addressed questions about the heating systems and followed up to ensure that everything was working properly. We enjoyed walking through the neighborhood, watching deer in the backyard, and the views...
MINNeSTAY *Modern Chic | Host Christmas*
Secluded Lakefront Home with outdoor hot tub, fire pit & indoor Hockey Rink
Smart TV, fireplace, printers

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

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

9.8 out of 10, Exceptional, (28)
"Perfect for our family of 16. Beds were all very comfortable, many options for activities which was great considering the crummy weather. Hosts are quick to respond and very accommodating. Great experience overall."
Charming and spacious 5 bedroom, 3 bath,19 guest home on peaceful keewahtin 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.
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Other property types in Osceola

Hudson Inn & Suites
Lobby

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very good, (685)
"They should have shoveled the sidewalks, it had snowed only an inch or so. None the less they should have shoveled for safety reasons "
The price is €87
includes taxes & fees
9 Feb - 10 Feb
Hudson Inn & Suites
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
Terrace/patio

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 €105
includes taxes & fees
26 Jan - 27 Jan
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
Romantic getaway! With gorgeous views from the Hot Tub!
Outdoor spa tub

Romantic getaway! With gorgeous views from the Hot Tub!

9.4 out of 10, Exceptional, (83)
"Great!"
The price is €234
includes taxes & fees
26 Jan - 27 Jan
Romantic getaway! With gorgeous views from the Hot Tub!
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.