Osceola Holiday 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
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Osceola holiday rentals

Exterior

Beautiful Waterfront Home on Baugo Bay

Beautiful Waterfront Home on Baugo Bay
Osceola
9.4 out of 10, Exceptional, (40 reviews)
"Great stay and great host!"
United States
jennifer
The price is HK$3,918
HK$5,146 total
includes taxes & fees
2 Jun - 3 Jun
Beautiful Waterfront Home on Baugo Bay
Property grounds

Relax and unwind at the Cozy Cabin on Heaton Lake.

Relax and unwind at the Cozy Cabin on Heaton Lake.
Elkhart
10.0 out of 10, Exceptional, (34 reviews)
"Fantastic place to stay"
United States
Kimberley G.
The price is HK$987
HK$1,652 total
includes taxes & fees
1 Jun - 2 Jun
Relax and unwind at the Cozy Cabin on Heaton Lake.
Interior

Cozy place in country settings, only 5 min from ND. No parties allowed however.

Cozy place in country settings, only 5 min from ND. No parties allowed however.
Mishawaka
10.0 out of 10, Exceptional, (49 reviews)
"So peaceful and such a beautiful property. Host was super quick with communication."
United States
KELLE
The price is HK$1,058
HK$1,397 total
includes taxes & fees
4 Jun - 5 Jun
Cozy place in country settings, only 5 min from ND. No parties allowed however.
Smart TV, books

Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife

Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife
Vandalia
10.0 out of 10, Exceptional, (79 reviews)
"Such a great stay! We very much enjoyed the cabin and recommend for a relaxing, peaceful trip."
United States
Natalie C.
The price is HK$1,587
HK$2,419 total
includes taxes & fees
3 Jun - 4 Jun
Couples Hideaway, Hot Tub, Private, Gazebo, Serene, Country, Birds, Wildlife
3 bedrooms

Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is HK$1,214
HK$2,545 total
includes taxes & fees
3 Jun - 4 Jun
Hidden Log Cabin Hot Tub Ping Pong Family
Outdoor spa tub

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Middlebury
10.0 out of 10, Exceptional, (65 reviews)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
The price is HK$1,550
HK$2,829 total
includes taxes & fees
11 Jun - 12 Jun
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Property grounds

Secluded Country Cabin

Secluded Country Cabin
Berrien Springs
10.0 out of 10, Exceptional, (75 reviews)
"We had a great stay! We loved the privacy and the wedding gift the owners gave to us!"
United States
Savannah L.
The price is HK$1,097
HK$1,434 total
includes taxes & fees
1 Jun - 2 Jun
Secluded Country Cabin
Property grounds

Cozy little lake cottage on Buck Lake!

Cozy little lake cottage on Buck Lake!
Vandalia
10.0 out of 10, Exceptional, (16 reviews)
"This was a wonderful place for a retreat--quiet and peaceful. I loved walking in Lawless County Park as well (just a short walk from the cottage)"
United States
Gail M.
The price is HK$1,072
HK$1,754 total
includes taxes & fees
1 Jun - 2 Jun
Cozy little lake cottage on Buck Lake!
TV

The Row House on 4th

The Row House on 4th
Dowagiac
The price is HK$1,008
HK$2,126 total
includes taxes & fees
1 Jun - 2 Jun
The Row House on 4th
Exterior

Vintage Romance Finds Cozy Charm at Depot Cottage

Vintage Romance Finds Cozy Charm at Depot Cottage
Dowagiac
9.2 out of 10, Wonderful, (17 reviews)
"Heather is very accommodating and communicates very well."
United States
Jeff B.
The price is HK$1,008
HK$2,126 total
includes taxes & fees
1 Jun - 2 Jun
Vintage Romance Finds Cozy Charm at Depot Cottage
TV, offices

Rivers Edge Lofts - Unit 4

Rivers Edge Lofts - Unit 4
Niles
9.2 out of 10, Wonderful, (17 reviews)
"It was a great stay with a fantastic stay with a great location."
United States
Patty B.
Rivers Edge Lofts - Unit 4
Beach

Rivers Edge Lofts - Unit 2

Rivers Edge Lofts - Unit 2
Niles
9.2 out of 10, Wonderful, (28 reviews)
"Nice location. "
United States
Todd
The price is HK$585
HK$1,039 total
includes taxes & fees
1 Jun - 2 Jun
Rivers Edge Lofts - Unit 2
Beach

Rivers Edge Lofts - Unit 5

Rivers Edge Lofts - Unit 5
Niles
9.6 out of 10, Exceptional, (31 reviews)
"Love the unique quaint setup in beautiful Niles, MI on the rivers edge. I would recommend for others"
United States
Sharon
The price is HK$626
HK$1,082 total
includes taxes & fees
2 Jun - 3 Jun
Rivers Edge Lofts - Unit 5
Beach

Be home away from home @ Charming Chestnut Cottage

Be home away from home @ Charming Chestnut Cottage
Dowagiac
8.4 out of 10, Very good, (9 reviews)
"Always a welcoming environment at Heathers places. It was nicely decorated for the holidays as well! "
United States
Diana G.
The price is HK$1,091
HK$1,991 total
includes taxes & fees
8 Jun - 9 Jun
Be home away from home @ Charming Chestnut Cottage
3 bedrooms

Hot Tub The Strong Retreat Fire Pit 3BR

Hot Tub The Strong Retreat Fire Pit 3BR
2.0 star property
Elkhart
Hot Tub The Strong Retreat Fire Pit 3BR
Beach

Rivers Edge Lofts - Unit 10

Rivers Edge Lofts - Unit 10
Niles
9.4 out of 10, Exceptional, (37 reviews)
"It was a beautiful place very clean and nice definitely gonna book it again"
United States
Adam D.
The price is HK$665
HK$1,137 total
includes taxes & fees
2 Jun - 3 Jun
Rivers Edge Lofts - Unit 10
Exterior

Ideal Bell Tent for a Glamping Experience on a Farm with all the Amenities in Niles, MI

Ideal Bell Tent for a Glamping Experience on a Farm with all the Amenities in Niles, MI
Niles
The price is HK$1,270
HK$1,544 total
includes taxes & fees
1 Jun - 2 Jun
Ideal Bell Tent for a Glamping Experience on a Farm with all the Amenities in Niles, MI
Smart TV, books

ND Irish homestead, mins away from ND Stadium, Memorial Hospital

ND Irish homestead, mins away from ND Stadium, Memorial Hospital
River Park
9.8 out of 10, Exceptional, (32 reviews)
"Great location! "
United States
Kristin C.
The price is HK$423
HK$1,343 total
includes taxes & fees
3 Jun - 4 Jun
ND Irish homestead, mins away from ND Stadium, Memorial Hospital
Terrace/patio

Romantic Cozy Home in "America’s Nicest Town"

Romantic Cozy Home in "America’s Nicest Town"
Buchanan
9.8 out of 10, Exceptional, (17 reviews)
"Very comfortable home in excellent location. Very well furnished and maintained."
United States
Jan P.
The price is HK$906
HK$1,780 total
includes taxes & fees
1 Jun - 2 Jun
Romantic Cozy Home in "America’s Nicest Town"
Terrace/patio

Cozy Quiet at Mill Pond Cottage

Cozy Quiet at Mill Pond Cottage
Dowagiac
8.2 out of 10, Very good, (12 reviews)
"Clean house, well equiped, very quiet location, easy access to fishing, caught mostly bluegills and a bass. Comfortable stay for 4 people. We did not have a pet but dogs are welcome. "
United States
Gregory
The price is HK$1,387
HK$2,583 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Quiet at Mill Pond 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

Wingate by Wyndham South Bend/Notre Dame

Wingate by Wyndham South Bend/Notre Dame

6/10 Okay
"When I walked in the room the tv was turned on and on mute. The bedside table lamp was not working I checked the plug and it never came on, that is an inconvenience for someone that needs that light. The shower head is very old the water pipe the shower head was attached to was wobbly. The associate when I checked in gave horrible directions to my room and the way the rooms are numbered makes no sense. I walked down several hallways until I finally found my room. I carried my heavy bags all over that place and I didn’t appreciate it. Unless it’s one of the only options left I don’t intend to stay here again."
Theresa 1-night trip
Posted less than an hour 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 holiday rentals in Osceola?

Yes, there are holiday rentals close to the most popular sights in Osceola, or you can select a more secluded option if you're looking for a relaxing stay.

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

Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL: This highly rated holiday home rental in Osceola is located on a river, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub. Another good choice for your trip to Osceola is Beautiful Waterfront Home on Baugo Bay.

How many holiday rentals are there in Osceola?

Choose from 8 Expedia holiday rentals in Osceola for a memorable holiday.

What’s there to see and do in Osceola?

Explore the area and family-friendly sights such as Strikes and Spares Entertainment Center, or get out into nature at a spot like Merrifield Pool. Mishawaka Fieldhouse and Midwest Museum of American Art are a couple of places you'll find in the wider area.

What’s a holiday rental in Osceola like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osceola. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.