Search Hotels with Pool in Osceola

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Check availability on Osceola Hotels with Pool

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Osceola hotels with a pool

Indoor pool
Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center
3.5 star property
Middlebury
9.8 out of 10, Exceptional, (1003)
"Everything was great my family & I have been going there for years.The atmosphere is just wonderful highly recommend it."
United States
Elsa
Essenhaus Inn & Conference Center
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
La Quinta Inn & Suites by Wyndham Elkhart

La Quinta Inn & Suites by Wyndham Elkhart

La Quinta Inn & Suites by Wyndham Elkhart
3.0 star property
Elkhart
7.6 out of 10, Good, (1004)
"Everything good, and clean I really recommend this hotel"
United States
Yony
The price is ฿2,190
฿2,452 total
includes taxes & fees
11 Jan - 12 Jan 2026
La Quinta Inn & Suites by Wyndham Elkhart
Indoor pool
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury
2.5 star property
Middlebury
8.4 out of 10, Very good, (1004)
"Clean room, friendly staff,pool area was great. "
United States
Steven T
The price is ฿3,410
฿3,819 total
includes taxes & fees
18 Jan - 19 Jan 2026
Hampton Inn & Suites Middlebury
Indoor pool
Fairfield Inn & Suites by Marriott Goshen

Fairfield Inn & Suites by Marriott Goshen

Fairfield Inn & Suites by Marriott Goshen
2.5 star property
Goshen
9.0 out of 10, Wonderful, (379)
"Staff super friendly clean place "
United States
Elizabeth
The price is ฿3,139
฿3,516 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Goshen
Indoor pool
Holiday Inn Express Hotel & Suites Goshen by IHG

Holiday Inn Express Hotel & Suites Goshen by IHG

Holiday Inn Express Hotel & Suites Goshen by IHG
2.5 star property
Goshen
8.0 out of 10, Very good, (620)
"Clean rooms, friendly staff and easy check-in "
United States
Sarah
The price is ฿2,731
฿3,059 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express Hotel & Suites Goshen by IHG
Outdoor spa tub
Four Winds Casino South Bend

Four Winds Casino South Bend

Four Winds Casino South Bend
3.0 star property
South Bend
9.6 out of 10, Exceptional, (765)
"Safe parking .excellent check in hosts."
United States
STEVEN J
The price is ฿2,765
฿3,457 total
includes taxes & fees
4 Jan - 5 Jan 2026
Four Winds Casino South Bend
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
Comfort Suites Elkhart North

Comfort Suites Elkhart North

Comfort Suites Elkhart North
2.5 star property
Elkhart
8.6 out of 10, Excellent, (477)
"nice place, comfortable bed, friendly service "
United States
Henry
The price is ฿2,035
฿2,280 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Suites Elkhart North
Indoor pool
avid Hotels Elkhart North by IHG

avid Hotels Elkhart North by IHG

avid Hotels Elkhart North by IHG
2.5 star property
Elkhart
9.2 out of 10, Wonderful, (352)
"Helpful, kind staff."
United States
Joanne
The price is ฿2,203
฿2,468 total
includes taxes & fees
4 Jan - 5 Jan 2026
avid Hotels Elkhart North by IHG
Seasonal outdoor pool
Amish Inn

Amish Inn

Amish Inn
2.0 star property
Nappanee
8.6 out of 10, Excellent, (407)
"Excellent stay for the weekend"
United States
Meghan
The price is ฿2,765
฿3,097 total
includes taxes & fees
31 Dec - 1 Jan 2026
Amish Inn
Seasonal outdoor pool
Baymont by Wyndham Elkhart

Baymont by Wyndham Elkhart

Baymont by Wyndham Elkhart
2.5 star property
Elkhart
7.4 out of 10, Good, (1002)
"Clean room and friendly staff"
United States
Kim
The price is ฿2,084
฿2,334 total
includes taxes & fees
1 Jan - 2 Jan 2026
Baymont by Wyndham Elkhart
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

Wingate by Wyndham South Bend/Notre Dame

Wingate by Wyndham South Bend/Notre Dame

10/10 Excellent
"The room and bathroom were both nice and clean. Everyone I interacted with was really polite. The complimentary breakfast was what i expected, but still enjoyable. I will definitely be staying here again."
Kara 2-night trip
Posted 6 days ago
Wingate by Wyndham South Bend/Notre Dame

Frequently asked questions

What are some accommodation options with pools in Osceola?
Doubletree Hotel South Bend: Hotel located near University of Notre Dame. Features complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Four Winds Casino South Bend: Offers 5 restaurants, a seasonal outdoor pool and a full-service spa. The Inn at Saint Mary's: Hotel located near University of Notre Dame. Features full, an indoor pool and free self parking. La Quinta Suites by Wyndham South Bend Notre Dame Area: Hotel located near University of Notre Dame. Offers a seasonal outdoor pool, an indoor pool and a snack bar/deli. Wingate by Wyndham South Bend/Notre Dame: Resort located near University of Notre Dame. Features free self parking, an indoor pool and complimentary wireless Internet access.
What is there to see and do in Osceola?
The picturesque settings of Wellfield Botanic Gardens and NIBCO Water and Ice Park showcase the area's natural beauty. During your stay, visit sights such as Elkhart Tactical Laser Tag, Mishawaka Fieldhouse and Midwest Museum of American Art.
When is the best time to book a hotel with a pool in Osceola?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Osceola in the hottest months of July, August or June, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temperature is -1°C.