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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Browse Select Osceola Holiday Homes

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, (35)
"We had a great stay!"
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.
Stillwater's Third Street Inn
Property grounds

Stillwater's Third Street Inn

10.0 out of 10, Exceptional, (215)
"The host and the house were both amazing. We had a great time exploring the area and just hanging out at the house in the evenings. We would definitely stay here again."
Stillwater's Third Street Inn
Historic Swedish Cottage on Quiet Lindstrom Lake
Exterior

Historic Swedish Cottage on Quiet Lindstrom Lake

9.4 out of 10, Exceptional, (219)
"Very homey, open spaces in home for a group to be together. Easy walk to interesting shops. Felt safe to take walks in. Beautiful lake side location."
The price is £508
includes taxes & fees
2 Sept - 3 Sept
Historic Swedish Cottage on Quiet Lindstrom Lake
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, (72)
"Very nice house to stay in. Clean, comfortable and close to main street!Would definitely stay again!"
Blocks to Downtown. Charming 3 Bed, Entire House
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, (24)
"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!
The Historic Roney House
Exterior

The Historic Roney House

The Historic Roney House
Cozy 3BR Home in Oakdale with BBQ & Private Patio!
Fridge, microwave, oven, stovetop

Cozy 3BR Home in Oakdale with BBQ & Private Patio!

10.0 out of 10, Exceptional, (1)
"Thank you for the comfortable accommodations during our stay in Minneapolis. The check in was seamless, convenient to local activities and check out was hassle free. "
Cozy 3BR Home in Oakdale with BBQ & Private Patio!
Cozy Lodge Theme Home in Beautiful Hudson, WI
Fridge, microwave, oven, stovetop

Cozy Lodge Theme Home in Beautiful Hudson, WI

9.6 out of 10, Exceptional, (74)
"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
Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
Private kitchen

Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse

9.8 out of 10, Exceptional, (9)
"The Place was perfect, beautiful better than the pictures. "
The price is £513
includes taxes & fees
24 Aug - 25 Aug
Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
Historic Stillwater Home close to downtown
Exterior

Historic Stillwater Home close to downtown

10.0 out of 10, Exceptional, (46)
"The owner is super friendly and very prompt in responding. The home is beautiful, cozy and clean. Beds were comfortable and there was AC in both bedrooms. The grounds are well manicured and peaceful. Off street parking and a nice little coffee bar. Highly recommend and we would definitely love to come back! Very convenient to downtown as well."
The price is £259
includes taxes & fees
31 Aug - 1 Sept
Historic Stillwater Home close to downtown
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

9.4 out of 10, Exceptional, (44)
"Nice and spacious."
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
Stovetop, dishwasher, paper towels

Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

10.0 out of 10, Exceptional, (5)
The price is £187
includes taxes & fees
25 Aug - 26 Aug
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
Lumberjack Inn 2300 sq.ft in DT with a rooftop
Terrace/patio

Lumberjack Inn 2300 sq.ft in DT with a rooftop

9.8 out of 10, Exceptional, (31)
"Property was clean, welcoming, and well situated in downtown Stillwater. Rooftop seating area was awesome. Very responsive hosts. Will stay again!"
Lumberjack Inn 2300 sq.ft in DT with a rooftop
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, (38)
"Our family had a really good time."
Charming and spacious 5 bedroom, 3 bath,19 guest home on peaceful keewahtin lake
Riverfront cabin with kayaks and canoes
Exterior

Riverfront cabin with kayaks and canoes

9.8 out of 10, Exceptional, (115)
"Everything was wonderful "
Riverfront cabin with kayaks and canoes
Cozy cottage in downtown Hudson, WI!
Outdoor dining

Cozy cottage in downtown Hudson, WI!

10.0 out of 10, Exceptional, (148)
"In town for our daughter’s wedding :) We had a very nice stay in this clean and comfortable home! "
Cozy cottage in downtown Hudson, WI!
MINNeSTAY* The Happy Home | Ski |
Fridge, microwave, oven, stovetop

MINNeSTAY* The Happy Home | Ski |

10.0 out of 10, Exceptional, (10)
"We loved this clean, modern home with the indoor sport court. We would definitely rent here again!!"
MINNeSTAY* The Happy Home | Ski |
Lake front-Fishing-Snowmobile Trails Nearby!
Property grounds

Lake front-Fishing-Snowmobile Trails Nearby!

9.2 out of 10, Wonderful, (21)
"Great space and great location. Bedrooms are spacey and cozy. We’d love to return in the summer!"
Lake front-Fishing-Snowmobile Trails Nearby!
Kayaks - Firepit - Dock - Fishing & more!
Outdoor dining

Kayaks - Firepit - Dock - Fishing & more!

9.8 out of 10, Exceptional, (30)
"enjoyed the peaceful area and lake"
Kayaks - Firepit - Dock - Fishing & more!
Gathering families, friends, & coworkers
Exterior

Gathering families, friends, & coworkers

9.8 out of 10, Exceptional, (36)
"This was an amazing property for our large family to gather together to celebrate Christmas. There was plenty of sleeping, dining and gathering space."
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.
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Top Osceola Hotel Reviews

Hotel Crosby

Hotel Crosby

10/10 Excellent
"Everything!!! Loved the restaurant, roof top hot tub, the room, staff... "
Christina 1-night trip
Posted 3 days ago
Hotel Crosby