A suspension bridge over a river with autumn foliage and houses in the background.

Osceola Vacation Rentals

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

Our top choices for Osceola vacation rentals

A living room with a fireplace, a bookshelf, and a large mirror.

1. Hot Tub The Strong Retreat Fire Pit 3BR

Hot Tub The Strong Retreat Fire Pit 3BR
2.0 star property
Elkhart
The price is ￥19,270
￥47,525 total
includes taxes & fees
Oct 6 - Oct 7
Hot Tub The Strong Retreat Fire Pit 3BR
A bedroom with a bed, bedside tables, a nightstand, a mirror, and a ceiling light fixture.

2. 1 Mi to Notre Dame, 4br, Private Yard and Pets

1 Mi to Notre Dame, 4br, Private Yard and Pets
3.0 star property
Northeast South Bend
The price is ￥20,678
￥90,399 total
includes taxes & fees
Oct 4 - Oct 5
1 Mi to Notre Dame, 4br, Private Yard and Pets
An outdoor hot tub area with a wooden bench, a small table with a candle, and string lights.

3. Hot Tub Outdoor Living Game Room Coffee Bar

Hot Tub Outdoor Living Game Room Coffee Bar
2.0 star property
South Bend
The price is ￥35,903
￥72,383 total
includes taxes & fees
Oct 11 - Oct 12
Hot Tub Outdoor Living Game Room Coffee Bar
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

4. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
The price is ￥25,797
￥49,551 total
includes taxes & fees
Oct 15 - Oct 16
Amish Country Getaway Farm Views Fire Pit
A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

5. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is ￥54,783
￥85,524 total
includes taxes & fees
Oct 16 - Oct 17
Hidden Log Cabin Hot Tub Ping Pong Family
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

6. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ￥19,270
￥45,532 total
includes taxes & fees
Oct 6 - Oct 7
Farm Country Amish Country Newly Renovated
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

Wingate by Wyndham South Bend/Notre Dame

Wingate by Wyndham South Bend/Notre Dame

10/10 Excellent
"The Wingate in South Bend was delightful. If I wanted my room serviced it was done when I got back that night. It was clean, comfortable, safe, and the staff were very friendly. I appreciated the refrigerator and microwave for use when I needed it. I would stay there again!"
Thelma 4-night trip
Posted 4 hours ago
Wingate by Wyndham South Bend/Notre Dame

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
  • Use the map to find apartments and other holiday homes in the Osceola neighbourhood you prefer
  • 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

Are there vacation rentals in Osceola?

Yes, we have vacation rentals near well known local attractions in Osceola, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Osceola?

Vacation at Garver Lake ~ Private Beach For Your Enjoyment!: Visitors like this Osceola vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Osceola?

Choose from 7 Expedia vacation rentals in Osceola for a memorable vacation.

What’s there to see and do in Osceola?

Explore the area and family-friendly sights such as National New York Central Railroad Museum, or get out into nature at a spot like Wellfield Botanic Gardens. Elkhart Tactical Laser Tag and Mishawaka Fieldhouse are a couple of places you'll find in the larger area.

What’s a vacation rental in Osceola like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Osceola. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips.