Osceola Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Osceola vacation rentals

Exterior

Beautiful Waterfront Home on Baugo Bay

Beautiful Waterfront Home on Baugo Bay
Osceola
9.4 out of 10, Exceptional, (38 reviews)
"Great stay and great host!"
United States
jennifer
$569 nightly
The price is $654
Apr 14 - Apr 15
Total with taxes and fees
Beautiful Waterfront Home on Baugo Bay
House

Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
$222 nightly
The price is $237
Apr 13 - Apr 14
Total with taxes and fees
Amish Country Getaway Farm Views Fire Pit
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, (29 reviews)
"Fantastic place to stay"
United States
Kimberley G.
$169 nightly
The price is $181
Apr 20 - Apr 21
Total with taxes and fees
Relax and unwind at the Cozy Cabin on Heaton Lake.
Outdoor spa tub

| Hot Tub | Amish Farm Country | Pergola | Deck |

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (96 reviews)
"This was a fantastic Vrbo stay and perfect little getaway! The home was clean, cozy and relaxing...exactly what I needed for two nights. Check-in/check-out was smooth, and the host was responsive and friendly. Great location and highly recommend! Absolutely would stay here again."
United States
Phil M.
$239 nightly
The price is $241
Apr 13 - Apr 14
Total with taxes and fees
| Hot Tub | Amish Farm Country | Pergola | Deck |
Property grounds

Cozy little lake cottage on Buck Lake!

Cozy little lake cottage on Buck Lake!
Vandalia
10.0 out of 10, Exceptional, (14 reviews)
"Well maintained and nicely stocked residence, exceptionally clean and comfortably decorated home. We had a great time during our brief one night stay for a family wedding. "
United States
Michele Lynn M.
$271 nightly
The price is $271
Apr 13 - Apr 14
Total with taxes and fees
Cozy little lake cottage on Buck Lake!
Terrace/patio

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Milford
10.0 out of 10, Exceptional, (34 reviews)
"We very much enjoyed our stay. The pool and hot tub were amazing and the home was thoughtfully prepared. We would definitely love to stay here again. "
United States
Mariah C.
$309 nightly
The price is $346
Apr 13 - Apr 14
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Apartment (2 Bedrooms) | Interior

Game Day Made Easy! Apt 2 Mi to Notre Dame Stadium

Game Day Made Easy! Apt 2 Mi to Notre Dame Stadium
3.0 star property
Near Northwest
$126 nightly
The price is $140
Apr 13 - Apr 14
Total with taxes and fees
Game Day Made Easy! Apt 2 Mi to Notre Dame Stadium
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.
$252 nightly
The price is $265
Apr 13 - Apr 14
Total with taxes and fees
Vintage Romance Finds Cozy Charm at Depot Cottage
Exterior

The Grain Binn: Stunning Magical Secluded Hot tub Lux Couples, Stillness, Belong

The Grain Binn: Stunning Magical Secluded Hot tub Lux Couples, Stillness, Belong
Vandalia
10.0 out of 10, Exceptional, (22 reviews)
"Amazing place to stay!! Such a cool location, great host great communication. Thanks again for an amazing stay."
United States
Mike H.
$433 nightly
The price is $470
Apr 23 - Apr 24
Total with taxes and fees
The Grain Binn: Stunning Magical Secluded Hot tub Lux Couples, Stillness, Belong
Living area

The Gemini

The Gemini
Elkhart
9.2 out of 10, Wonderful, (13 reviews)
"Very clean, had everything we needed and the host was great to communicate with. One of the best places we have ever stayed."
United States
Kelly C.
$136 nightly
The price is $146
Apr 19 - Apr 20
Total with taxes and fees
The Gemini
Smart TV, DVD player, foosball, books

River Retreat W/ HOT TUB/ Game room

River Retreat W/ HOT TUB/ Game room
Bristol
10.0 out of 10, Exceptional, (31 reviews)
"This is a great place for friends and family to congregate. It is out of the way, so you get some privacy and yet it is not a far drive from restaurants, groceries, and activities. If you like the outdoors and would enjoy a riverside retreat, this place is a great option! "
United States
Kenneth G.
$836 nightly
The price is $895
May 1 - May 2
Total with taxes and fees
River Retreat W/ HOT TUB/ Game room
House

Hot Tub The Strong Retreat Fire Pit 3BR

Hot Tub The Strong Retreat Fire Pit 3BR
2.0 star property
Elkhart
$271 nightly
The price is $290
Apr 19 - Apr 20
Total with taxes and fees
Hot Tub The Strong Retreat Fire Pit 3BR
Property grounds

Secluded Country Cabin

Secluded Country Cabin
Berrien Springs
10.0 out of 10, Exceptional, (74 reviews)
"We had a great stay! We loved the privacy and the wedding gift the owners gave to us!"
United States
Savannah L.
$181 nightly
The price is $181
Apr 13 - Apr 14
Total with taxes and fees
Secluded Country Cabin
Interior

Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country
Nappanee
10.0 out of 10, Exceptional, (12 reviews)
"Clean, courteous and a great place to get away from distractions and burdens and relax!!! Wife and I are really looking forward to visiting soon."
United States
Go N.
$174 nightly
The price is $186
May 7 - May 8
Total with taxes and fees
Woodside Retreat in the Heart of Amish Country
Interior

Rivers Edge Lofts - Unit 1

Rivers Edge Lofts - Unit 1
Niles
9.8 out of 10, Exceptional, (52 reviews)
"It was a beautiful place. Reminded us of a room that Joanna Gaines would have decorated. Very pretty. Great location for our weekend getaway!"
United States
Michelle B.
Rivers Edge Lofts - Unit 1
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, (39 reviews)
"Perfect place for a quick, ND get away."
United States
Marisa H.
$155 nightly
The price is $178
Apr 13 - Apr 14
Total with taxes and fees
Cozy place in country settings, only 5 min from ND. No parties allowed however.
Smart TV, books

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

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife
Vandalia
10.0 out of 10, Exceptional, (77 reviews)
"Very beautiful and cozy cabin. The host was responsive and you can tell he cares about the guests and cabin. "
United States
Matthew O.
$241 nightly
The price is $250
Apr 15 - Apr 16
Total with taxes and fees
Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife
Terrace/patio

The Sanctuary at Eby Farms

The Sanctuary at Eby Farms
Cassopolis
10.0 out of 10, Exceptional, (24 reviews)
"The place was beautifully done. The shower is outdoors (on the porch) but that didn't bother us at all. Overall great place to stay especially if you're attending a wedding at the venue just around the corner."
United States
Kristin E.
$202 nightly
The price is $212
Apr 13 - Apr 14
Total with taxes and fees
The Sanctuary at Eby Farms
Fridge, microwave, oven, stovetop

Lakeshore Cottage

Lakeshore Cottage
Elkhart
9.8 out of 10, Exceptional, (18 reviews)
"We had a great trip here to cheer on ND!"
United States
Megan B.
$479 nightly
The price is $512
Apr 14 - Apr 15
Total with taxes and fees
Lakeshore Cottage
Beach

Be home away from home @ Charming Chestnut Cottage

Be home away from home @ Charming Chestnut Cottage
Dowagiac
8.0 out of 10, Very Good, (8 reviews)
"Always a welcoming environment at Heathers places. It was nicely decorated for the holidays as well! "
United States
Diana G.
$217 nightly
The price is $228
Apr 13 - Apr 14
Total with taxes and fees
Be home away from home @ Charming Chestnut 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.
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Top Osceola Hotel Reviews

Morris Inn

Morris Inn

10/10 Excellent
"Great staff great beds"
Bernadette 2-night trip
Posted 8 hours ago
Morris Inn

Find out more about Osceola

Everything you need to know about Osceola vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osceola vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osceola in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $178 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osceola rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osceola vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osceola. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL: Visitors like this Osceola vacation home rental. It is located on a river and has an outdoor pool, a balcony, 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. Kick off your shoes and enjoy yourself with a garden and a hot tub.

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 Potawatomi Zoo, or get out into nature at a spot like Merrifield Pool. 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.