A waterfall cascading over a rocky cliff surrounded by lush greenery.

Holiday Homes in Osceola

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Osceola holiday homes

A kitchen with wooden cabinets, a window, a sink, and various kitchen utensils.

1. Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (85 reviews)
"Rooms are clean, kitchen is well supplied. If you enjoy staying at historic buildings, this would be a good fit for you."
United States
Kathleen R.
The price is NZ$388
includes taxes & fees
6 Oct - 7 Oct
Historic 1880s Home
A campsite with a tent, a grill, and outdoor seating.

2. Lovers Lookout 2 at Big Rock Creek

Lovers Lookout 2 at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"We enjoyed everything about our stay! Just wish we had more time to enjoy the amenities of the property. "
United States
Kim J.
The price is NZ$273
includes taxes & fees
12 Oct - 13 Oct
Lovers Lookout 2 at Big Rock Creek
A modern living room with a spiral staircase, a sofa set, a coffee table, and a chandelier.

3. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (44 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
The price is NZ$692
includes taxes & fees
5 Oct - 6 Oct
Scandinavian Retreat
A wooden cabin with a triangular roof, a central door, and a small window.

4. The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"Great experience"
United States
Lori M.
The price is NZ$319
includes taxes & fees
30 Sept - 1 Oct
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
A dock with two boats, a wooden deck, and a small outdoor seating area.

5. Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (10 reviews)
"VRBO makes a quick getaway so seamless. Stayed in town for a family wedding and could not have been happier with the location. Great rooftop bar with craft cocktails and good beer wine selection. Soon to have restaurant. Gift/essential shop below bar. Really nice people and great view."
United States
Karie S.
The price is NZ$489
includes taxes & fees
30 Sept - 1 Oct
Nordic Harbor | Room 5 | Cedar Shadows
A two-story house with a wooden deck, large windows, and a covered porch area.

6. Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.

Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
center city
10.0 out of 10, Exceptional, (9 reviews)
"We had a wonderful time staying in this beautiful house. House was very clean, well decorated and had everything we needed.Quiet location but only minutes away from great wineries and restaurants.Highly recommend!"
United States
Karen M.
The price is NZ$815
includes taxes & fees
30 Sept - 1 Oct
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
A kitchen with wooden cabinets, a granite countertop, a window with a faucet, and a black doormat.

7. Classic Home

Classic Home
Centuria
8.2 out of 10, Very good, (41 reviews)
"Nice clean house that fit our needs perfectly. Were on girls weekend and this was great place to stay and then travel around the wider area trying different routes and restaurants. Got great suggestions from the host! "
United States
Melissa
The price is NZ$398
includes taxes & fees
30 Sept - 1 Oct
Classic Home
A bedroom with a wooden ceiling, a bed with a white comforter and patterned pillows, a bedside table with a lamp, and a small table with a potted plant.

8. Nordic Harbor | Room 1 | Acorn Oak

Nordic Harbor | Room 1 | Acorn Oak
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was wonderful---quaint, modern-rustic and very comfortable. We loved being able to walk across the parking lot to the rooftop bar."
United States
Alisha H.
The price is NZ$537
includes taxes & fees
8 Oct - 9 Oct
Nordic Harbor | Room 1 | Acorn Oak
Property grounds

9. Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (250 reviews)
"Second time staying at this property with a group and it was excellent once again!"
United States
Leah O.
The price is NZ$1,291
includes taxes & fees
13 Oct - 14 Oct
Historic Swedish Cottage on Quiet Lindstrom Lake
A compact kitchen with a microwave, a sink, and a small countertop.

10. Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce
Center City
The price is NZ$544
includes taxes & fees
4 Oct - 5 Oct
Nordic Harbor | Room 4 | Nordic Spruce
A large, historic building with a prominent tower and arched windows, featuring a classic architectural style.

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

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Balsam Lake Village
9.0 out of 10, Wonderful, (44 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is NZ$398
includes taxes & fees
28 Oct - 29 Oct
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
A wooden interior with a ceiling fan, a woven rug, and a view through a glass door to another room.

12. Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking

Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
Somerset
10.0 out of 10, Exceptional, (3 reviews)
"Very nice,clean property. The only thing it needs is a little more seating in the living room area. A couch would be very nice. We would definitely stay there again."
United States
Trina P.
The price is NZ$1,037
includes taxes & fees
30 Sept - 1 Oct
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
A spacious living room with wooden floors, two sofas, a coffee table, and a large rug.

13. Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
White Bear Lake
9.4 out of 10, Exceptional, (10 reviews)
"House very clean and well stocked."
United States
Brad H.
The price is NZ$625
includes taxes & fees
13 Oct - 14 Oct
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
A cozy living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

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

Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
Stillwater
9.4 out of 10, Exceptional, (21 reviews)
"Very spacious and comfortable."
United States
Joan I.
Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
A dock with two boats, a wooden deck, and a sandy area with a small chair and table.

15. Nordic Harbor | Room 6 | Silver Birch - Suite

Nordic Harbor | Room 6 | Silver Birch - Suite
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Do not hesitate to book at Nordic Harbor. The rooms are stellar and the location is convenient. Steps away from the room is the Nordic Harbor market and roof top bar. The onsite pontoon rental is a blast, and the lake is beautiful. If you're looking for a quick getaway from the cities, this is it!"
United States
Paul F.
The price is NZ$792
includes taxes & fees
11 Oct - 12 Oct
Nordic Harbor | Room 6 | Silver Birch - Suite
A dining area with a wooden table, grey upholstered chairs, and a tray with beverages and snacks.

16. Relaxing Townhouse Escape

Relaxing Townhouse Escape
Hugo
9.2 out of 10, Wonderful, (25 reviews)
"Nice clean place. Perfect for what we needed."
United States
Sara C.
The price is NZ$631
includes taxes & fees
30 Sept - 1 Oct
Relaxing Townhouse Escape
A spacious kitchen with a large island, wooden cabinets, and a stainless steel refrigerator.

17. 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
9.6 out of 10, Exceptional, (14 reviews)
"Excellent place to stay. We will definitely be returning. Host was very accommodating."
United States
Judy K.
The price is NZ$1,184
includes taxes & fees
4 Oct - 5 Oct
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
A two-story house with a front porch, brick facade, and a garage.

18. Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (88 reviews)
"Our host was lovely, the property was great, and our stay was one to remember. I can't wait to come back and explore this cute community more in the future!"
United States
Katelyn F.
The price is NZ$657
includes taxes & fees
18 Oct - 19 Oct
Historic Stillwater Home close to downtown
A spacious living room with a high ceiling, large windows, a red leather sofa, floral-patterned armchairs, a coffee table, and a wooden cabinet with decorative items.

19. Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage
North Saint Paul
9.8 out of 10, Exceptional, (16 reviews)
"Comfortable beds and clean bathrooms."
United States
Angelika
The price is NZ$499
includes taxes & fees
7 Oct - 8 Oct
Minne-GetAway: Modern Cottage
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osceola Hotel Reviews

Country Inn & Suites by Radisson Stillwater MN

Country Inn & Suites by Radisson Stillwater MN

10/10 Excellent
"The room was great! I particularly liked the expanded countertop in the bathroom area. A very nice upgrade to the usual hotel bath. Staff was excellent on check in and check out as well."
Jill 3-night trip
Posted 13 hours ago
Country Inn & Suites by Radisson Stillwater MN

Find out more about Osceola

Osceola Holiday Homes information

Number of reviews
653
Accommodation
161 Holiday Homes
Lowest Price
NZ$273
Highest Price
NZ$1,291