Osceola Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Osceola holiday rentals

Interior

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (75 reviews)
"Beautiful home and beautiful vibe. Would visit again!"
United States
Janice
The price is HK$1,402
HK$1,766 total
includes taxes & fees
13 May - 14 May
Historic 1880s Home
Exterior

Cozy Mother-in-Law Apartment

Cozy Mother-in-Law Apartment
Osceola
10.0 out of 10, Exceptional, (51 reviews)
"Would absolutely stay here again! Lovely location, clean, communicative host, and they shoveled right when it snowed which was especially helpful when I had a 5am clinical rotation!"
United States
Mallorey K.
The price is HK$768
HK$1,022 total
includes taxes & fees
11 May - 12 May
Cozy Mother-in-Law Apartment
Desk, iron/ironing board, free WiFi, bed sheets

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (824 reviews)
"Comfy and clean. "
United States
Melissa
The price is HK$559
HK$666 total
includes taxes & fees
10 May - 11 May
Hudson Inn & Suites
Dining

Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!

Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!
Amery
9.6 out of 10, Exceptional, (15 reviews)
"Very clean, comfortable cabin, beautiful area, nice fire pit area, love the large soaking tub! "
United States
Deb P.
The price is HK$1,022
HK$1,683 total
includes taxes & fees
11 May - 12 May
Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!
Exterior

Where Comfort Meets Adventure — In Every Season!

Where Comfort Meets Adventure — In Every Season!
Saint Croix Falls
9.8 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay so much! There is a lot to do around the area and our cabin was cozy & relaxing. Thank you!"
United States
Pwggy D.
The price is HK$1,088
HK$2,233 total
includes taxes & fees
11 May - 12 May
Where Comfort Meets Adventure — In Every Season!
Exterior detail

Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
Somerset
9.8 out of 10, Exceptional, (9 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is HK$1,233
HK$1,804 total
includes taxes & fees
22 May - 23 May
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
1 bedroom, iron/ironing board, WiFi, bed sheets

Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (8 reviews)
"We had a great stay. Nordic Harbor is a very charming, clean and comfortable boutique hotel! We really enjoyed the patio out back of our room and the rooftop bar overlooking the lake with live music out front of the hotel. We will be back and bring our boat next time!"
United States
Erica F.
The price is HK$1,880
HK$2,434 total
includes taxes & fees
10 May - 11 May
Nordic Harbor | Room 5 | Cedar Shadows
Dining

1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!
Amery
9.6 out of 10, Exceptional, (18 reviews)
"It was a perfect cozy cabin with updated amenities. Had a great stay!"
United States
Carissa S.
The price is HK$869
HK$1,437 total
includes taxes & fees
12 May - 13 May
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!
Exterior

Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (14 reviews)
"Very nice cozy cabin and such a great, accommodating host! "
United States
Jesse S.
The price is HK$1,214
HK$2,156 total
includes taxes & fees
12 May - 13 May
Lake Home property
Exterior

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (70 reviews)
"We enjoyed the location and amenities of this home. Our group of 4 adults and 3 infants were able to spread out and sleep comfortably, the house write up was accurate and the homey touches provided a wonderful space to relax and reconnect. We enjoyed our stay!"
United States
Crystal R.
The price is HK$1,762
HK$2,644 total
includes taxes & fees
10 May - 11 May
Historic Stillwater Home close to downtown
Interior

Home on the Apple River

Home on the Apple River
Amery
10.0 out of 10, Exceptional, (4 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
The price is HK$1,010
HK$1,726 total
includes taxes & fees
20 May - 21 May
Home on the Apple River
Smart TV

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (39 reviews)
"Amazing place! Super cute and close to lots of attractions. Hosts were great communicating and providing a welcoming stay with clear instructions. "
United States
Olivia W.
The price is HK$1,234
HK$2,762 total
includes taxes & fees
11 May - 12 May
Scandinavian Retreat
Smart TV, fireplace

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (9 reviews)
"Very conveniently located to downtown Taylors Falls and Interstate Park so we could walk everywhere!"
United States
Allison G.
The price is HK$1,174
HK$1,681 total
includes taxes & fees
13 May - 14 May
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Smart TV

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
Stillwater
9.4 out of 10, Exceptional, (59 reviews)
"Enjoyed our stay in stillwater. Host is very responsive and the property is amazing. The location is perfect for a getaway. We have enjoyed the property before and plan too again "
United States
Michael M.
The price is HK$1,472
HK$2,966 total
includes taxes & fees
17 May - 18 May
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
Property grounds

Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (239 reviews)
"Great stay, beautiful views, comfortable. and clean."
United States
CHRISTOPHER
The price is HK$3,328
HK$5,767 total
includes taxes & fees
10 May - 11 May
Historic Swedish Cottage on Quiet Lindstrom Lake
Interior

Luxurious remodel near historic downtown Hudson!

Luxurious remodel near historic downtown Hudson!
Hudson
10.0 out of 10, Exceptional, (31 reviews)
"Perfect for a girls get away! "
United States
Anne D.
The price is HK$3,086
HK$3,773 total
includes taxes & fees
10 May - 11 May
Luxurious remodel near historic downtown Hudson!
Fridge, microwave, oven, stovetop

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
Stillwater
9.8 out of 10, Exceptional, (6 reviews)
"Excellent place to stay. We will definitely be returning. Host was very accommodating."
United States
Judy K.
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
Terrace/patio

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (35 reviews)
"The hosts were super accommodating and made a last minute booking happen! The space is super cute and just what I needed. I also loved how close it was to downtown Stillwater "
United States
Courtney E.
The price is HK$1,096
HK$2,072 total
includes taxes & fees
12 May - 13 May
Private Suite in historic Stillwater North Hill
Outdoor dining

Nordic Harbor | Room 3 | Arctic Pine - Suite

Nordic Harbor | Room 3 | Arctic Pine - Suite
Center City
10.0 out of 10, Exceptional, (1 review)
"Beautiful place and will be staying there again. "
United States
SUZANNE M.
The price is HK$2,741
HK$3,495 total
includes taxes & fees
10 May - 11 May
Nordic Harbor | Room 3 | Arctic Pine - Suite
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

8/10 Good
"Hotel Crosby was beautiful. Only downfall was the uncomfortable mattresses and pillows. The mattresses were very thin and lumpy."
Carla 2-night trip
Posted 16 hours ago
Hotel Crosby

Find out more about Osceola

Search for holiday rentals in Osceola on Expedia! You can easily find your home rentals, villas, holiday apartments in Osceola using one of the methods below:

  • View our selection of featured holiday rentals in Osceola
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  • Enter your travel dates to view the best deals on holiday rentals in Osceola while they last

Look no further and take a look at our great range of rental properties in Osceola!

Frequently asked questions

Can I find a holiday rental in Osceola?

Yes, there are holiday rentals in Osceola close to Osceola & St. Croix Valley Railway, or you can select a more secluded option if you're looking for a relaxing stay. Osceola is known for its riverfront and bars. Make sure you have time to check out the waterfalls and entertainment choices during your trip.

What are some of the best holiday rentals that Osceola has to offer?

Cozy Lodge Theme Home in Beautiful Hudson, WI: This holiday home rental outside of Osceola is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Osceola?

Choose from 6 Expedia holiday rentals in Osceola for a memorable holiday.

What can I see and do in Osceola?

Farmington Bottoms State Natural Area and Saint Croix River are a couple of lovely local spots to get outside and enjoy nature. Osceola & St. Croix Valley Railway and Trollhaugen are other places to visit while you're in town.

What are holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.