Photo by Erik Rowley
Open Photo by Erik Rowley
Osceola County Vacations & Trips from $356
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Osceola County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hyatt Regency Bloomington - Minneapolis
Sep 22 - Sep 24Hyatt Regency Bloomington - Minneapolis + Flight
East Bloomington2 nights4.0 star property9.2/10 - Wonderful (2,417 reviews)"Rooms were nice and clean. Mattress comfy but not sheets. No working fridge and empty ice machines...no brewed complimentary coffee in the morning and pricey not included breakfast."Reviewed July 19, 2026Roundtrip • Chicago (CHI) - Minneapolis (MSP)RFD - MSP • 1 stop MSP - MDW • Nonstop$444$356found 1 day agoper traveler - Emery, Autograph Collection Hotel
Oct 13 - Oct 16Emery, Autograph Collection Hotel + Flight
Downtown Minneapolis3 nights4.5 star property9.2/10 - Wonderful (758 reviews)"Perfect location to walk to the major sport venues plus the river front"Reviewed July 19, 2026Roundtrip • New York (NYC) - Minneapolis (MSP)JFK - MSP • Nonstop MSP - JFK • Nonstop$960$713found 4 hours agoper traveler - Four Seasons Hotel Minneapolis
Sep 15 - Sep 17Four Seasons Hotel Minneapolis + Flight
Downtown Minneapolis2 nights5.0 star property9.6/10 - Exceptional (343 reviews)"Our family very much enjoyed staying here. The property is beautiful and the staff went above and beyond to make sure that we were taken care of. We have stayed at many of the top resorts in the world, and this did not disappoint. We will definitely be back to stay again."Reviewed July 12, 2026Roundtrip • Chicago (CHI) - Minneapolis (MSP)RFD - MSP • 1 stop MSP - ORD • Nonstop - Moxy Minneapolis Downtown
Sep 15 - Sep 17Moxy Minneapolis Downtown + Flight
Downtown Minneapolis2 nights3.0 star property9.0/10 - Wonderful (899 reviews)Roundtrip • Chicago (CHI) - Minneapolis (MSP)RFD - MSP • 1 stop MSP - ORD • Nonstop$508$401found 3 hours agoper traveler - The Lofton Hotel, Tapestry Collection by Hilton
Sep 15 - Sep 17The Lofton Hotel, Tapestry Collection by Hilton + Flight
Downtown Minneapolis2 nights4.5 star property9.4/10 - Exceptional (1,071 reviews)Roundtrip • Chicago (CHI) - Minneapolis (MSP)RFD - MSP • 1 stop MSP - ORD • Nonstop$669$535found 3 hours agoper traveler
Discover the most popular places to visit in Osceola County
Osceola County Hotel Deals
9.2 out of 10, Wonderful, (456 reviews)
9.2/10
Wonderful
(456 reviews)
"Sibley Inn was a clean, friendly and relatively quiet motel sitting close to the railroad tracks. It was a decent room at a decent price. Would stay there again."
$67 nightly
The price is $74
$74 total
Aug 10 - Aug 11
Total with taxes and fees
9.2 out of 10, Wonderful, (299 reviews)
9.2/10
Wonderful
(299 reviews)
"The room is clean and quiet. The bed is comfortable. The staff is very helpful."
$107 nightly
The price is $118
$118 total
Jul 26 - Jul 27
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.